Old Money Hairstyles: Timeless & Refined Looks for Men

The most sought-after Old Money Hairstyles, including the Classic Side Part, Slick Back, and Ivy League cut, are deeply rooted in upper-class tradition and refinement. These haircuts for men are characterized by their emphasis on clean lines, meticulous grooming, and enduring appeal, projecting an image of understated wealth and sophistication.

Key Considerations for Choosing Your Old Money Hairstyle

• Face Shape and Hair Texture Harmony: Select a style that complements your unique facial structure and hair type.
• Lifestyle and Upkeep Commitment: Factor in your daily routine and the level of maintenance each hairstyle demands.
• Age-Appropriate Elegance: Choose styles that not only reflect your age but also enhance your overall appearance with timeless grace.

Eager to delve deeper? Continue exploring the full article below to discover the nuances of each iconic style ↓

1. The Classic Side Part: A Paragon of Timeless Style

Classic Side Part Old Money Hairstyle

Alt text: A man with a neatly styled classic side part hairstyle, embodying old money elegance.

The classic side part stands as a quintessential hairstyle for men, distinguished by its sharp, well-defined part that elegantly divides the hair, typically extending from the crown to the temple. The hallmark of this cut is the subtly longer hair on top, meticulously styled to one side, contrasted by neatly tapered or faded sides that ensure a crisp, clean silhouette.

The Enduring Appeal of the Classic Side Part in Old Money Aesthetics

Emerging in the sophisticated eras of the 1920s and 1930s, the Classic Side Part quickly became a hallmark of refined taste. Popularized by Hollywood icons like Cary Grant and Fred Astaire, it represented a shift from the longer, slicked-back styles of previous decades, evolving into a potent symbol of refined masculinity.

Cary Grant and Fred Astaire Old Money Hairstyle The Classic Side Part

Alt text: Black and white portrait of Cary Grant and Fred Astaire, iconic figures showcasing the classic side-part hairstyle, embodying old money charm.

With its precise lines and structured form, the Classic Side Part inherently communicates order and discipline, core values deeply embedded within the old-money style. This hairstyle is not merely a cut; it’s a statement of timeless elegance and considered grooming.

Ideal Hair Specifications for the Classic Side Part

The Classic Side Part is most effectively executed on medium to fine hair types, ideally with a subtle natural wave that aids in maintaining volume and shape. The hair on top should be sufficiently long to allow for a defined comb-over and part, typically ranging from 2 to 4 inches. The sides are kept shorter, usually between 0.5 and 1 inch, to enhance the structured contrast. The goal is to achieve a balanced volume that upholds the style’s inherent structure without appearing overly rigid or dense.

Celebrities Who Champion the Classic Side Haircut

• Jon Hamm: His portrayal of Don Draper in “Mad Men” has solidified the Classic Side Part as a modern style reference, embodying mid-century sophistication.

Jon Hamm Classic Side Part Old Money Hairstyle

Alt text: Jon Hamm, portraying Don Draper, exemplifies the classic side part hairstyle, a modern icon of old money style.

• George Clooney: His silver fox side part is a celebrated example of the classic side part in old money hairstyles, radiating mature charisma.

George Clooney Classic Side Part Old Money Hairstyle

Alt text: George Clooney, showcasing his silver fox classic side part, a distinguished example of old money hairstyle elegance.

• David Beckham: This British icon has frequently showcased various adaptations of the Classic Side Part, underscoring the cut’s lasting appeal and adaptability.

David Beckham Classic Side Part Old Money Hairstyle

Alt text: David Beckham, sporting a modern iteration of the classic side part, illustrating its enduring versatility in old money hairstyles.

• Ryan Gosling: Gosling’s interpretation of the side part includes a slightly longer top with a more relaxed, textured finish, offering a contemporary twist on the classic.

Ryan Gosling Classic Side Part Old Money Hairstyle

Alt text: Ryan Gosling, presenting his classic side part hairstyle, a subtly textured and relaxed take on old money grooming.

Essential Styling Techniques for the Classic Side Part

• Begin with hair that is damp, ideally towel-dried, and apply a small amount of pomade or styling cream, focusing application from the roots to the ends.
• Utilize a fine-toothed comb to create a precise and distinct part, starting from the crown and moving towards the temple.
• Blow-dry the hair on top towards the defined part, employing a round brush to introduce volume and smoothness.
• For a more casual iteration, gently use your fingers to tousle the hair on top, ensuring the part’s structure remains intact.

Facial Hair Pairings for the Classic Side Part

The Classic Side Part is ideally complemented by a clean-shaven face, enhancing the sharp, polished appearance. However, a well-groomed mustache or a meticulously trimmed beard can also harmonize with this style, adding a touch of vintage charm or modern sophistication.

Recommended Hair Products for the Classic Side Part

Opt for a high-quality pomade or styling cream that offers medium to firm hold with a subtle sheen, such as Baxter of California’s Hard Water Pomade or Creed’s Green Irish Tweed Hair Pomade. A lightweight hair spray, like R+Co’s Outer Space Flexible Hairspray, is also advisable for enhanced hold and frizz control.

Maintenance Regimen and Barber Visits

Regular trims every 3-4 weeks are crucial to maintain the Classic Side Part’s defined and sharp aesthetic. Ensure your barber is well-versed in the nuances of this style to tailor the cut to your face shape and hair type. Between professional cuts, daily maintenance includes refining the part and restyling as needed.

The Classic Side Part remains a cornerstone of old-money hairstyles, offering a versatile and timeless look that elegantly suits a broad spectrum of face shapes and personal styles.

2. The Slick Back: Effortless Sophistication Personified

Slick Back Old Money Hairstyle

Alt text: A man showcasing a sleek slick back hairstyle, embodying the refined essence of old money aesthetics.

The Slick Back hairstyle is a timeless and sophisticated choice that exudes tasteful refinement. It is achieved by meticulously brushing the hair back and away from the face, creating a sleek appearance that speaks volumes of understated elegance.

The Historical Prestige of the Slick Back in Old Money Style

The Slick Back hairstyle gained significant traction during the 1920s and 1930s, a period often hailed as the Golden Age of Hollywood. Icons such as Clark Gable and Humphrey Bogart championed this look, making it synonymous with the quintessential suave gentleman.

Clark Gable and Humphrey Bogart Slick Back Old Money Hairstyle

Alt text: Black and white image of Clark Gable and Humphrey Bogart, classic movie stars with slick back hairstyles, epitomizing old money sophistication.

The Slick Back’s deep-rooted association with the old-money aesthetic stems from its inherent ability to project confidence, refinement, and an aura of effortless style, traits highly valued in elite circles.

Optimal Hair Characteristics for the Slick Back

The Slick Back performs best with medium to thick hair type that possesses a slight natural wave or straight texture. The hair should be sufficiently long to be combed back and maintain the style effectively, ideally around 3-5 inches on top and 1-2 inches on the sides and back. The key is to achieve a balanced volume that results in a smooth, sleek appearance without looking flat or devoid of life.

Celebrities Synonymous with the Slick Back Hairstyle

• Leonardo DiCaprio: His portrayal in “The Great Gatsby” with a Slick Back flawlessly captured the old-money charm and sophistication associated with this iconic hairstyle.

Leonardo DiCaprio Slick Back Old Money Hairstyle

Alt text: Leonardo DiCaprio in “The Great Gatsby,” sporting a slick back hairstyle that perfectly embodies old money glamour.

• Michael Douglas: Known for his consistently sleek and polished Slick Back, Douglas embodies mature and sophisticated style.

Michael Douglas Slick Back Old Money Hairstyle

Alt text: Michael Douglas, showcasing his signature slick back hairstyle, a hallmark of mature old money elegance.

• Jake Gyllenhaal: Gyllenhaal often opts for a contemporary Slick Back, demonstrating its versatility across different eras and styles.

Jake Gyllenhaal Slick Back Old Money Hairstyle

Alt text: Jake Gyllenhaal, wearing a modern slick back hairstyle, illustrating its adaptability and contemporary old money appeal.

Mastering the Styling of the Slick Back

• Begin with damp, towel-dried hair and apply a modest amount of pomade or hair gel, ensuring even distribution from the roots to the ends.
• Use a wide-toothed comb to meticulously slick the hair back, starting from the forehead and moving towards the crown.
• For a high-gloss finish, refine the look using a fine-toothed comb to achieve an exceptionally smooth and even surface.
• Blow-dry the hair in a backward direction, utilizing a concentrator nozzle for a sleeker outcome. Conclude by applying additional pomade or hair spray to enhance hold and shine.

Facial Hair Options for the Slick Back

The Slick Back is ideally paired with a clean-shaven face, accentuating the sophisticated appearance. However, a well-maintained beard or mustache can introduce a touch of masculinity and create a more contemporary, edgy aesthetic.

Essential Hair Products for the Slick Back

A high-quality pomade with a strong hold and high shine, such as Layrite’s Super Hold Pomade or Suavecito’s Firme Hold Pomade, is crucial. For a sleeker, wet-look finish, a medium-hold hair gel like American Crew’s Firm Hold Styling Gel is also recommended.

Maintenance and Barber Appointments for the Slick Back

Regular trims, ideally every 4-6 weeks, are advisable to maintain the Slick Back’s polished appearance. Ensure your barber understands the specific nuances of this style to tailor the cut appropriately to your hair type and face shape. Daily restyling is necessary to uphold the Slick Back’s signature look, using the recommended products and techniques.

The Slick Back is a quintessential old-money hairstyle, offering a timeless and sophisticated look that can be effectively adapted to suit a variety of face shapes and personal styles.

3. The Ivy League: Scholarly Chic with Refined Elegance

Ivy League Old Money Hairstyle

Alt text: A man with an impeccably styled Ivy League hairstyle, reflecting scholarly chic and old money refinement.

The Ivy League hairstyle is a classic, Preppy look that perfectly encapsulates refined scholarly elegance. It is a timeless haircut characterized by a short, neat overall appearance, featuring a subtle quiff at the front, precisely tapered sides, and a sharp side part.

The Academic Pedigree of the Ivy League Hairstyle

Named after the prestigious Ivy League universities in the United States, such as Harvard, Yale, and Princeton, the Ivy League style first emerged in the 1920s. It quickly gained favor among the young, affluent gentlemen attending these esteemed institutions.

Ivy League Prep University Life 1930s 1940s

Alt text: Vintage photo of Ivy League university life in the 1930s-1940s, illustrating the historical context of the Ivy League hairstyle.

Projecting an image of elite education and intellectual prowess, the Ivy League haircut embodies the old-money aesthetic through its strong association with establishments that have long been bastions of wealth, power, and enduring influence.

Ideal Hair Specifications for the Ivy League Cut

Fine to medium hair with a slight natural wave is optimally suited for a flawless Ivy League haircut. This hair texture allows for a neat, structured appearance while still maintaining a touch of natural movement. The hair on top should be kept relatively short, just long enough to create a small, subtle quiff at the front. Aim for a top length of around 1-2 inches, providing sufficient volume and height without appearing overly dramatic. The sides and back should be tapered shorter, gradually fading from approximately 1 inch at the top to about 0.5 inches near the ears and neckline. This precise tapering is essential for creating a clean, polished look, reinforcing the hairstyle’s crisp lines and refined silhouette, hallmarks of classic men’s haircut styles.

Celebrities Who Exemplify the Ivy League Scholarly Chic Hairstyle

• John F. Kennedy: As a style icon, JFK epitomized the Ivy League haircut, linking it to political prestige and classic American style.

John F. Kennedy Ivy League Hairstyle

Alt text: John F. Kennedy, a style icon, with his signature Ivy League haircut, embodying classic American old money style.

• Ryan Gosling: Gosling often sports a modern interpretation of the Ivy League haircut, highlighting its versatility and enduring appeal across generations.

Ryan Gosling Ivy League Hairstyle

Alt text: Ryan Gosling, showcasing a contemporary Ivy League haircut, demonstrating its timeless appeal and modern old money adaptation.

Styling Techniques for the Ivy League Haircut

• Apply a small amount of pomade or styling cream to slightly damp hair, focusing on the roots and distributing the product through to the ends using your fingers.
• Create a crisp side part using a fine-toothed comb, starting from the crown and extending towards the temple.
• Use a blow dryer set to medium heat and speed to dry the hair on top, employing a small round brush to generate volume and a subtle quiff at the front.
• Once dry, refine the quiff using your fingers or a comb to ensure a neat, structured finish.

Facial Hair Recommendations for the Ivy League Style

The Ivy League haircut is best complemented by a clean-shaven face, which accentuates the style’s neat, polished appearance and draws attention to its clean lines and refined silhouette. However, a well-groomed mustache can be an excellent option for gentlemen seeking to add a touch of vintage charm and sophistication. A classic mustache style, such as the chevron or pyramidal, can enhance the Ivy League’s old-money aesthetic, subtly nodding to the style icons of a bygone era.

Recommended Hair Products for the Ivy League Cut

• Baxter of California Clay Pomade: A water-based pomade providing medium hold and a matte finish, ideal for achieving the Ivy League’s structured yet natural-looking style.
• American Crew Forming Cream: With a light to medium hold and low-shine finish, perfect for achieving the Ivy League’s polished yet understated appearance.
• Oribe’s Superfine Hair Spray: A lightweight hair spray is essential for maintaining the Ivy League haircut’s shape and protecting against humidity and frizz.

Maintenance Schedule and Barber Visits for the Ivy League

Maintaining the Ivy League haircut’s clean, structured appearance requires regular trims every 3-4 weeks. This frequency ensures the hair on top remains at the ideal length for crafting the style’s signature quiff, while keeping the tapered sides and back impeccably neat.

The Ivy League haircut is a timeless old-money style that projects an air of intelligence, refinement, and understated elegance, making it a perennial choice for those seeking a sophisticated and academically inspired look.

4. The Taper Fade: Modern Refinement with Classic Roots

Taper Fade Old Money Hairstyle

Alt text: A man with a meticulously executed taper fade hairstyle, blending contemporary style with old money elegance.

The taper fade is a contemporary hairstyle that seamlessly merges the classic elegance of old-money aesthetics with fresh, clean cuts, appealing to today’s discerning gentlemen. This haircut is defined by a gradual tapering from longer lengths on the top to progressively shorter lengths on the sides and back, creating a smooth, blended transition that is both modern and sophisticated.

The Historical Underpinnings of the Taper Fade in Old Money Style

While the taper fade has surged in popularity in recent years, its origins are rooted in the classic, clean-cut hairstyles favored by the wealthy and influential throughout the 20th century. Gaining prominence in the 1940s, the taper fade’s emphasis on neatness, structure, and precision resonates deeply with the timeless values of the old-money aesthetic.

Taper Fade Hairstyle History

Alt text: Historical image showcasing the taper fade hairstyle’s evolution, highlighting its roots in classic grooming and old money aesthetics.

Simultaneously, its modern interpretation allows for enhanced flexibility and personal expression, making it a versatile choice for those who appreciate both tradition and contemporary style. The taper fade serves as an excellent bridge between traditional and contemporary styling, making it a go-to choice for gentlemen seeking to project elegance in both professional and social settings.

Ideal Hair Versatility for the Taper Fade

The taper fade is remarkably versatile, adaptable to a broad spectrum of hair types, textures, and lengths. However, for achieving the most polished and refined results, it is best to start with hair that has a medium to fine texture and a moderate amount of natural volume. The ideal length for the top portion of the hair depends on your personal styling preferences, but a range of 1-4 inches is generally recommended. This length provides ample scope for various styling options, from sleek and smooth to textured and tousled, while maintaining the taper fade’s signature blended appearance. Regarding volume, the objective is to achieve a balanced, proportional look that enhances your facial features and head shape.

Celebrities Who Master the Taper Fade Hairstyle

• Justin Timberlake: Timberlake’s sleek, polished taper fades showcase the hairstyle’s versatility and ability to complement various personal styles and occasions, from red-carpet events to laid-back, casual settings.

Justin Timberlake Taper Fade Old Money Hairstyle

Alt text: Justin Timberlake, demonstrating a polished taper fade haircut, highlighting its versatility in contemporary old money style.

• Ryan Reynolds: Reynolds’ clean-cut, yet slightly textured, taper fades exemplify how this style can be adapted to suit various personal styles and occasions, from red-carpet events to casual, everyday settings.

Ryan Reynolds Taper Fade Old Money Hairstyle

Alt text: Ryan Reynolds, sporting a clean-cut taper fade, showcasing its adaptability for both formal and casual old money looks.

• Michael B. Jordan: Jordan’s taper fades, characterized by precise, graduated cuts, feature crisp lines and sharp fades that highlight his chiseled features. The longer lengths on top allow for a range of stylish, textured looks, projecting an image of confidence and adaptability.

Michael B. Jordan Taper Fade Old Money Hairstyle

Alt text: Michael B. Jordan, featuring a sharp taper fade haircut, emphasizing its modern and confident appeal in old money grooming.

Styling Techniques for the Taper Fade

• Start with clean, towel-dried hair washed with high-quality shampoo and conditioner. Apply a small amount of styling product, such as pomade, clay, or cream, to the hair on top, working it through from roots to ends with your fingers or a comb.
• Use a blow dryer set to medium heat and speed to dry the hair on top, simultaneously using a round brush or your fingers to shape and style it in your preferred direction.
• Once the top portion is dry and styled, use a fine-toothed comb or soft-bristled brush to gently blend the longer hair on top with the tapered sides and back.
• To finish and ensure long-lasting hold, apply a small amount of hair spray or a light-hold styling product, such as grooming cream or texture spray, to the hair on top.

Facial Hair Pairings for the Taper Fade

The taper fade’s versatility extends to its compatibility with various facial hairstyles, allowing gentlemen to customize their looks to suit personal preferences and face shapes. A clean-shaven face is ideal for a clean cut, creating a refined appearance that emphasizes the taper fade’s structured silhouette. Alternatively, a well-groomed mustache, carefully trimmed beard, or precisely styled goatee can enhance the taper fade’s old-money aesthetic while allowing for a greater degree of personal expression and individuality.

Recommended Hair Products for the Taper Fade

To achieve and maintain the perfect taper fade, it is essential to use high-quality hair products that provide the right balance of hold, texture, and finish. Some recommended options include:

• Hanz de Fuko Claymation: A matte-finish styling product combining clay’s strength with wax’s flexibility, ideal for creating textured yet controlled taper fade styles.
• Uppercut Deluxe Pomade: For gentlemen preferring a sleeker, more polished taper fade, this pomade offers the perfect combination of medium hold and high shine.
• Baxter of California’s Clay Effect Style Spray: Excellent when a lightweight, texturizing finish is desired, adding subtle texture without stiffness.

Maintenance Schedule and Barber Visits for the Taper Fade

Depending on your hair’s natural growth rate and desired level of precision, it is recommended to schedule barber appointments every 2-4 weeks. This ensures the taper remains sharp and the overall style stays refined, hallmarks of old money grooming.

5. The Undercut: Bold Contrast with Refined Edges

Undercut Old Money Hairstyle

Alt text: A man confidently sporting an undercut hairstyle, showcasing its bold contrast and modern old money appeal.

The undercut is a striking, modern hairstyle that artfully combines the refined appeal of old-money aesthetics with a contemporary, daring twist. This attention-grabbing look features sharply short, buzzed sides and back, creating a dramatic contrast with the longer hair on top. The undercut is a bold hairstyle for men who aim to make a statement and stand out, departing from traditional, conservative styles typically associated with the old-money aesthetic, appealing to those who embrace individuality and modern flair.

The Rebellious Charm of the Undercut in Old Money Context

The undercut originated in the early 20th century and was initially popular among working-class men and military personnel. Recently, it has experienced a significant resurgence, becoming a favorite among fashion-forward gentlemen who appreciate its unique blend of classic refinement and rebellious attitude.

Undercut History

Alt text: Historical image illustrating the undercut hairstyle’s origins, showing its evolution into a modern style with old money undertones.

The undercut’s sharp contrast and precise lines echo the clean-cut, well-groomed appearance associated with the old-money aesthetic while pushing the boundaries of traditional styling, making it a bold yet sophisticated choice.

Ideal Hair Specifications for the Undercut

The undercut is best suited for men with straight or slightly wavy hair, as it relies on the stark contrast between the short sides and the longer top to achieve its distinctive look. The ideal length for the top portion is 2-5 inches, allowing for various styling options and dramatic volume. The sides and back are typically clipped very short, often with a #1 or #2 guard, or even fully buzzed, to maximize the sharp distinction between the top and sides, creating a bold, eye-catching silhouette.

Celebrities Who Champion the Undercut Hairstyle

• Brad Pitt: Pitt has frequently sported various undercut styles, demonstrating the hairstyle’s rugged, masculine appeal and its versatility across different looks.

Brad Pitt Undercut Old Money Haircut

Alt text: Brad Pitt, exemplifying the undercut haircut, showcasing its rugged masculinity and modern old money vibe.

• Adam Levine: Levine’s iconic undercut features a longer, textured top and closely cropped sides, perfectly embodying the style’s rock-and-roll edge and modern sophistication.

Alt text: Adam Levine, known for his undercut hairstyle, blending rock-and-roll edge with a modern take on old money grooming.

• Cillian Murphy: Murphy’s portrayal of Tommy Shelby in “Peaky Blinders” popularized a vintage-inspired undercut, combining sharp contrast with old-world sophistication, making it a culturally iconic style.

Alt text: Cillian Murphy as Tommy Shelby in “Peaky Blinders,” popularizing a vintage-inspired undercut with sharp lines and old money sophistication.

Styling Techniques for the Undercut

• Begin with clean, dry hair and apply a small amount of high-hold pomade or styling clay to the longer hair on top.
• Style the hair on top in your desired direction, creating volume, texture, and movement using a wide-toothed comb or fingers.
• Use a blow dryer on medium heat and speed, directing airflow at the roots while styling to achieve extra volume and lift.
• Apply a small amount of hairspray or texturizing spray to hold the style in place and add definition, ensuring the undercut maintains its bold shape throughout the day.

Facial Hair Options for the Undercut

The undercut’s edgy, masculine appeal makes it an ideal companion for various facial hairstyles. A well-groomed beard can add texture and visual interest, enhancing the overall ruggedness, while a clean-shaven face highlights the undercut’s sharp lines and bold contrast, emphasizing its modern aesthetic. Consider pairing your undercut with neatly trimmed stubble or a short, well-defined beard for a balanced, rugged yet refined look that aligns with a contemporary old money style.

Recommended Hair Products for the Undercut

• Layrite Cement Clay: Provides a firm, pliable hold with a natural, matte finish, ideal for creating textured, modern undercut styles that require strong control.
• Suavecito’s oil-based pomade: For a classic, slick look with high shine, this pomade offers superior hold and long-lasting control, perfect for achieving a traditional undercut style.
• Kevin Murphy Rough Rider clay: Provides a stronghold and a matte finish, suitable for various textures and styles of undercuts, offering versatility in styling.

Maintenance Schedule and Barber Visits for the Undercut

Maintain the undercut’s sharp appearance with regular barber visits every 2-3 weeks. This frequent maintenance is crucial to keep the sides and back sharply defined and the contrast between the short and long hair prominent. Between appointments, use quality hair products and restyle as needed to keep the undercut looking its best, reflecting a commitment to grooming and style.

6. The Classic Pompadour: Vintage Charm and Bold Volume

Classic Pompadour Old Money Hairstyle Men

Alt text: A man with a voluminous classic pompadour hairstyle, exuding vintage charm and old money sophistication.

The classic pompadour is a timeless hairstyle that exudes old-school sophistication and vintage charm. This iconic look features hair swept upward and back from the forehead, creating an impressive volume that commands attention. The pompadour is a daring choice for men who appreciate the refined, dapper aesthetics of a bygone era and is ideal for recalling the elegance and panache of classic Hollywood icons, making a bold statement with timeless style.

The Royal Roots and Hollywood Glamour of the Pompadour

With a rich history dating back to the 18th century, the pompadour hairstyle was named after Madame de Pompadour, a mistress of King Louis XV of France, highlighting its aristocratic origins. The style gained significant popularity in the 1950s and 1960s, worn by influential musicians and celebrities like Elvis Presley and Johnny Cash, cementing its status as a symbol of cool rebellion and classic charm.

Elvis Presley and Johnny Cash Classic Pompadour Haircut

Alt text: Black and white photo of Elvis Presley and Johnny Cash, iconic musicians with classic pompadour hairstyles, embodying vintage old money style.

The pompadour’s enduring appeal lies in its ability to convey confidence, charisma, and a touch of rebellion, all while maintaining a polished, well-groomed appearance that aligns seamlessly with old-money sensibilities, making it a powerful statement of style and personality.

Ideal Hair Characteristics for the Pompadour

Medium to thick hair with a slight natural wave is ideal for creating a classic pompadour. The hair should be long enough on top to achieve the signature swept-up look, typically 3-5 inches in length. The sides and back are kept shorter, usually tapered or faded, to emphasize the contrast and height of the pomp, drawing attention to its voluminous top. The key to a successful pompadour is achieving a balance of volume and control, ensuring the style looks impressive but not overly stiff or artificial, maintaining a natural yet sculpted appearance.

Celebrities Synonymous with the Pompadour Hairstyle

• Elvis Presley: Presley’s legendary pompadour became a defining feature of his iconic style, inspiring generations of fans to emulate his rebellious yet glamorous look, making it a cultural phenomenon.

Elvis Presley Classic Pompadour Old Money Hairstyle

Alt text: Elvis Presley, the king of rock and roll, with his iconic classic pompadour, a defining symbol of vintage old money style.

• James Dean: Dean’s effortlessly cool take on the pompadour helped cement the style’s association with rebellious, bad-boy charm, adding a layer of edgy sophistication to its classic roots.

James Dean Classic Pompadour Old Money Hairstyle

Alt text: James Dean, embodying cool rebellion with his classic pompadour, adding an edgy twist to old money hairstyles.

• David Beckham: Beckham has sported a modern version of the pompadour, showcasing the style’s versatility and ongoing relevance in contemporary fashion, proving its timeless appeal and adaptability.

David Beckham Pompadour Old Money Hairstyle

Alt text: David Beckham, presenting a modern pompadour hairstyle, demonstrating its contemporary relevance and versatile old money charm.

Styling Techniques for the Classic Pompadour

• Begin with damp, towel-dried hair and apply a generous amount of high-hold pomade or styling cream, working it evenly throughout the hair from roots to tips.
• Using a comb, create a side part if desired, then sweep the hair on top upward and back, starting from the forehead and working towards the crown to build volume.
• Use a blow dryer on medium-high heat, directing airflow at the roots while combing the hair back to maximize volume and height, shaping the signature pomp.
• Once the desired shape is achieved, use your fingers or a comb to refine the final look, ensuring a smooth, polished finish that highlights the pomp’s structure and volume.

Facial Hair Pairings for the Pompadour

A clean-shaven face is a traditional choice for the classic pompadour, highlighting the hairstyle’s crisp, polished appearance and ensuring the focus remains on the voluminous hair. However, a well-groomed mustache can add a touch of vintage flair and masculine charm, complementing the pompadour’s retro vibe. For a more contemporary take, a neatly trimmed beard can provide balance and texture, softening the style’s boldness while maintaining its old-money roots, offering a modern twist on a classic look.

Recommended Hair Products for the Pompadour

Achieving and maintaining a classic pompadour requires high-quality styling products with a stronghold and a medium- to high-shine finish.

• Layrite Super Hold Pomade: Provides a water-based, high-hold formula that keeps the pompadour firmly in place all day, offering reliable control and shine.
• Baxter of California’s Hard Cream Pomade: An excellent choice for a more natural, pliable hold with a subtle sheen, providing flexibility while maintaining shape.
• Suavecito Firme Hold Pomade: Offers a strong, long-lasting hold with a high-shine finish, perfect for a traditional, slick pompadour that demands maximum hold and gloss.

Maintenance Schedule and Barber Visits for the Pompadour

Regular barber visits every 3-4 weeks are crucial to maintaining the pompadour’s precise shape and neatly trimming the sides and back, ensuring the style remains sharp and defined. Daily styling with the appropriate products is necessary to ensure the pomp retains its volume and structure, requiring a consistent grooming routine to keep the pompadour looking its best.

7. The Quiff: Modern Volume with Classic Inspiration

Quiff Old Money Haircut

Alt text: A man showcasing a stylish quiff hairstyle, combining modern volume with classic old money inspiration.

The quiff is a modern hairstyle that elegantly combines elements of the classic pompadour with the 1950s-inspired slick back, creating a versatile and contemporary look. This cut features longer hair on top, styled up and back to create volume and height at the front, while the sides and back are kept shorter for a clean, modern silhouette. The quiff effectively balances the structured elegance of old-money hairstyles with the relaxed, textured appeal of modern styling, making it a popular choice for those seeking a blend of tradition and modernity.

The Evolution of the Quiff from Classic Styles

While the quiff is a relatively modern hairstyle, it draws significant inspiration from the classic pompadour, which has deep roots in old-money fashion and grooming traditions. Popularized by James Dean in the 1950s, the quiff’s emphasis on volume, height, and a polished finish echoes the refined aesthetics of traditional old-money hairstyles, while adapting them for a contemporary audience.

James Dean 50s Quiff Haircut

Alt text: James Dean, a 1950s icon, sporting a classic quiff haircut, illustrating the style’s historical roots and old money influences.

The quiff’s adaptability allows it to be styled in various ways, from more relaxed and tousled versions to highly structured and voluminous styles, reflecting the modern trend towards less structured, more natural-looking hair. This flexibility makes the quiff an ideal choice for gentlemen who want to incorporate elements of old-money sophistication into a contemporary, easy-to-manage style that suits various occasions.

Ideal Hair Specifications for the Quiff

The quiff works best with medium to thick hair that has a slight natural wave or straight texture, providing the necessary body and manageability for styling. The ideal length for the top portion is 2-4 inches, allowing for enough volume and height to create the signature quiff shape, while maintaining a balanced overall look. The sides and back should be shorter, usually between 0.5 and 2 inches, depending on the desired level of contrast and personal preference, creating a defined shape that emphasizes the quiff. The quiff’s volume can be customized to suit individual tastes, ranging from a more understated, textured look to a bold, sky-high statement, offering versatility in styling and impact.

Celebrities Who Exemplify the Quiff Hairstyle

• Zac Efron: Efron’s modern quiff features a textured, tousled top and shorter sides, showcasing the style’s youthful, effortless appeal and its ability to look both casual and stylish.

Zac Efron quiff old money hairstyle

Alt text: Zac Efron, sporting a modern quiff hairstyle, demonstrating its youthful appeal and contemporary old money style.

• Chris Pine: Pine’s sleek, voluminous quiff combines old-school sophistication with contemporary charm, making it a go-to choice for red-carpet events, highlighting its elegant and refined nature.

Chris Pine Quiff Old Money Hairstyle

Alt text: Chris Pine, showcasing a sleek and voluminous quiff, embodying old school sophistication and modern old money charm.

• David Gandy: Gandy’s classic quiff with a side part demonstrates the style’s versatility and ability to bridge the gap between traditional and modern aesthetics, offering a timeless yet contemporary look.

David Gandy Quiff Old Money Hairstyle

Alt text: David Gandy, presenting a classic quiff with a side part, illustrating its versatility and blend of traditional and modern old money styles.

Styling Techniques for the Quiff

• Begin with damp, towel-dried hair by applying a small pre-styling mousse or volumizing spray for added lift and hold, preparing the hair for styling.
• Using a blow dryer and a round brush, dry the hair on top up and back, focusing on creating volume at the roots and a smooth, curved shape for the quiff.
• Apply a small amount of pomade, clay, or styling cream to the hair, working it through with your fingers to add texture, definition, and hold, shaping and setting the quiff.
• For a more relaxed, tousled look, use your fingers to gently break up the quiff and create a natural, textured finish, providing a more casual and effortless style.

Facial Hair Options for the Quiff

The quiff’s modern, versatile nature allows it to be paired effectively with various facial hair styles, enhancing its overall appeal and adaptability. A clean-shaven face can highlight the quiff’s polished, sophisticated appearance, emphasizing its clean lines and volume. Alternatively, well-groomed stubble or a short beard can add a rugged, masculine edge, providing a contrast to the quiff’s refined top. For a more balanced look, consider pairing your quiff with a neatly trimmed mustache or goatee, which can complement the hairstyle’s classic and contemporary elements, creating a harmonious and stylish appearance.

Recommended Hair Products for the Quiff

• Hanz de Fuko Claymation: Provides a pliable, long-lasting hold with a natural, matte finish, making it ideal for creating textured, modern quiffs that require flexibility and control.
• Imperial Barber Classic Pomade: For a high-shine look, use a water-based pomade like this, offering excellent hold and a glossy finish that enhances the quiff’s volume and shape.

Maintenance Schedule and Barber Visits for the Quiff

To keep your quiff looking its best, schedule regular barber visits every 4-6 weeks to maintain the proper length and shape, ensuring the quiff remains defined and stylish. Between appointments, wash and condition your hair regularly and restyle it as needed using your preferred products, maintaining the quiff’s volume and shape on a daily basis.

8. The Crew Cut: Classic Simplicity and Low Maintenance

Military Crew Cut mens haircuts

Alt text: A man with a clean and sharp crew cut hairstyle, embodying classic simplicity and low maintenance old money grooming.

The crew cut is a classic, low-maintenance hairstyle characterized by short hair all around the head, with slightly longer hair on top that gradually tapers down to the sides and back. This timeless style offers a neat and practical look. The crew cut’s clean, masculine appearance and easy upkeep make it a popular choice for men who value simplicity and practicality without sacrificing style, making it a go-to for understated elegance.

The Collegiate and Military Heritage of the Crew Cut

The crew cut originated in the 1920s and 1930s as a popular haircut among university crew teams, hence its name, reflecting its early association with athleticism and collegiate life. During World War II, the hairstyle gained widespread popularity as a practical and low-maintenance cut for military personnel, cementing its reputation for functionality and neatness.

Crew Cut Men History

Alt text: Historical image of men’s crew cut hairstyles in the 1920s and 1930s, illustrating its collegiate and early old money origins.

The crew cut’s association with the old-money aesthetic lies in its neat, well-groomed appearance and connection to prestigious universities and military tradition, both of which are historically linked to upper-class society. The style’s simplicity and practicality align perfectly with the understated elegance and academic discipline associated with old-money families, making it a subtle yet sophisticated choice.

Ideal Hair Specifications for the Crew Cut

The crew cut works well with most hair types and textures, from fine to thick and straight to wavy, making it a versatile option for a wide range of men. The ideal length for a crew cut is between 1/2 inch to 1 inch on top, with the sides and back gradually tapering down to 1/8 inch or less, creating a clean and uniform look. The crew cut’s volume is minimal, as the short length keeps the hair close to the scalp, emphasizing its practicality and neatness. This low-volume, no-fuss style is perfect for men who prefer a neat, tidy appearance without requiring extensive styling or daily maintenance.

Celebrities Who Opt for the Crew Cut

• Ryan Reynolds: Reynolds often sports a classic crew cut, showcasing the style’s timeless appeal and ability to complement various face shapes, highlighting its versatility and enduring charm.

Ryan Reynolds Crew Cut

Alt text: Ryan Reynolds, sporting a classic crew cut, demonstrating its timeless appeal and versatile old money style across different face shapes.

• Tom Hardy: Hardy’s crew cut, often styled with slightly longer hair on top, adds a modern, textured twist to the traditional style, giving it a contemporary edge while maintaining its classic roots.

Tom Hardy Crew Cut

Alt text: Tom Hardy, showcasing a crew cut with slightly longer hair on top, adding a modern texture to this classic old money style.

• Channing Tatum: Tatum’s crew cut demonstrates the style’s versatility, as it effortlessly transitions from casual settings to more formal occasions, proving its adaptability and understated elegance.

Channing Tatum Crew Cut

Alt text: Channing Tatum, presenting a crew cut hairstyle, highlighting its versatility for both casual and formal old money occasions.

Styling Techniques for the Crew Cut

• Start with a small amount of matte pomade or styling cream on clean, damp hair, and apply from the top down, distributing it evenly with your fingers to enhance texture and control.
• Using a comb or your fingers, style the hair on top forward, to the side, or in a slightly messy, textured manner, depending on your desired look, allowing for customization within the crew cut’s neat framework.
• For a more polished appearance, brush or comb to smooth the hair on top and create a neat, uniform finish, emphasizing the crew cut’s clean and orderly nature.
• If desired, apply a small amount of hair wax or clay to the hair on top for added texture and definition, providing more styling options for those seeking a slightly more defined look.

Facial Hair Options for the Crew Cut

The crew cut’s clean, masculine appearance pairs well with various facial hairstyles, offering flexibility in grooming choices. A clean-shaven face can highlight the crew cut’s neat, polished look, emphasizing its clean lines and simplicity. Alternatively, well-groomed stubble or a short beard can add a rugged, masculine touch, providing a contrast to the crew cut’s neatness. For a balanced appearance, pair your crew cut with a neatly trimmed mustache or goatee, which can complement the hairstyle’s simple but refined nature, creating a harmonious and stylish overall look.

Recommended Hair Products for the Crew Cut

To maintain the crew cut’s neat appearance and add a touch of texture or definition, consider using the following products:

• American Crew Forming Cream: Provides a pliable, low-shine hold that helps to tame and style short hair, enhancing texture without stiffness, ideal for a natural look.
• Baxter of California Clay Pomade: For a matte, textured finish, try this clay pomade, which offers a strong, pliable hold without added shine, perfect for a more defined and textured crew cut.

Maintenance Schedule and Barber Visits for the Crew Cut

To keep your crew cut looking sharp and well-maintained, schedule regular barber visits every 2-4 weeks, depending on your hair growth and desired length, ensuring the crew cut remains neat and in shape. Between appointments, wash your hair regularly and style as needed with minimal product, maintaining the crew cut’s effortless style and cleanliness.

The crew cut is a timeless, low-maintenance hairstyle that embodies the clean, masculine aesthetics of old-money grooming, making it a practical yet stylish choice. The simplicity and practicality of this look make it a go-to choice for men who value a neat, polished appearance without needing extensive styling or upkeep, aligning with an understated and refined approach to grooming.

9. The Buzz Cut: Minimalist Confidence and Utilitarian Style

Classic Buzz Cut hairstyles

Alt text: A man with a classic buzz cut hairstyle, projecting minimalist confidence and utilitarian old money style.

The buzz cut is a minimalist, low-maintenance hairstyle that exudes confidence and masculinity. This simple yet assertive look involves cutting the hair very short all over the head, typically with electric clippers, resulting in a uniform length that usually ranges from 1/4 to 1/2 inch. The buzz cut’s clean, fuss-free appearance makes it a popular choice for men who value practicality and a no-nonsense approach to grooming, while still projecting a strong and confident image.

The Practical Appeal of the Buzz Cut in Old Money Circles

While the buzz cut is not traditionally considered an old-money hairstyle, its origins in the military and its emphasis on simplicity and practicality align with certain old-money aesthetics that value function and understated style. The buzz cut’s minimalist appearance and low-maintenance nature can be interpreted as a rejection of excess and a focus on functionality, qualities often associated with old-money values and a preference for understated elegance over ostentation.

Additionally, the buzz cut’s popularity among influential figures, such as actors, athletes, and business leaders, has helped to elevate its status and make it a timeless, classic choice for men across various social and economic backgrounds, further cementing its appeal beyond its utilitarian origins.

Ideal Hair Versatility for the Buzz Cut

The buzz cut works exceptionally well with most hair types and textures, from fine to thick and straight to curly, making it an incredibly versatile option. The uniform short length of the buzz cut effectively minimizes the appearance of volume and texture differences, making it a universally flattering choice for men with various hair types and textures. The ideal length for a buzz cut ranges from 1/4 inch to 1/2 inch, depending on personal preference and face shape, allowing for subtle variations in style. Shorter lengths can create a more severe, masculine look, while slightly longer lengths offer a touch more flexibility in styling, though the buzz cut remains inherently minimalist.

Celebrities Who Embrace the Buzz Cut

• David Beckham: Beckham has sported various buzz cut styles throughout his career, showcasing the look’s versatility and its ability to complement different face shapes and personal styles, proving its adaptability across diverse looks and settings.

David Beckham Buzz Cut

Alt text: David Beckham, showcasing a buzz cut hairstyle, demonstrating its versatility and enduring appeal in contemporary old money style.

• Zayn Malik: Malik’s buzz cut, often styled with a slightly longer top and faded sides, demonstrates how the style can be adapted to create a more modern, edgy appearance, adding a contemporary twist to the classic buzz cut.

Zayn Malik buzz cut

Alt text: Zayn Malik, featuring a buzz cut with a slightly longer top and faded sides, illustrating its modern and edgy adaptation for old money looks.

• Jason Statham: Statham’s iconic buzz cut has become a signature part of his tough, masculine image, perfectly illustrating the style’s ability to project confidence and strength, making it synonymous with his persona.

Styling Techniques for the Buzz Cut

• After showering, simply towel dry your hair or allow it to air dry, leveraging the buzz cut’s low-maintenance nature for effortless styling.
• If desired, apply a small amount of matte pomade or wax to the hair to add a hint of texture and definition, enhancing the buzz cut with subtle styling for a refined finish.
• For a more polished look, use a soft-bristled brush to smooth the hair and create a neat, uniform appearance, maintaining the buzz cut’s clean and sharp aesthetic with minimal effort.

Facial Hair Options for the Buzz Cut

The buzz cut’s minimalist, masculine appearance pairs exceptionally well with various facial hairstyles, offering flexibility in grooming choices. A clean-shaven face can highlight the cut’s sleek, streamlined look, emphasizing its clean lines and sharp profile. Alternatively, a well-groomed stubble or short beard can add a rugged, masculine edge, providing a contrast to the buzz cut’s simplicity. For a balanced and modern appearance, consider pairing your buzz cut with a neatly trimmed goatee or a short, well-defined beard, which can complement the hairstyle’s simple yet confident nature, creating a harmonious and contemporary look.

Recommended Hair Products for the Buzz Cut

Due to the buzz cut’s short length, minimal product is typically needed to maintain the style, emphasizing its low-maintenance appeal. However, the following products can help keep your hair looking healthy and add a touch of texture or definition if desired:

• American Crew Firm Hold Gel: Provides a strong, non-flaking hold with a low shine, perfect for adding a bit of control and definition to your buzz cut when a more styled look is desired.
• Baxter of California Grooming Cream: Offers a lightweight, nourishing formula that moisturizes the scalp and adds a subtle, matte finish to the hair, keeping the buzz cut looking healthy and naturally styled.

Maintenance Schedule and Barber Visits for the Buzz Cut

To maintain the buzz cut’s neat, uniform appearance, schedule regular barber visits every 2-3 weeks, depending on your hair growth and desired length, ensuring the buzz cut remains sharp and well-defined. Between appointments, wash your hair regularly with a gentle shampoo to keep the scalp clean and healthy, promoting overall scalp and hair health with minimal daily effort.

The buzz cut is a minimalist, confident hairstyle that perfectly embodies simplicity and practicality, aligning with an understated yet impactful approach to grooming. The fuss-free nature and masculine appearance of this cut make it an ideal choice for men who value a no-nonsense approach to grooming while still maintaining a stylish and confident look, reflecting a preference for functionality and understated elegance.

10. The Comb Over: Refined Sophistication with a Modern Twist

Comb Over Old Money Style Haircut

Alt text: A man with a modern comb over hairstyle, showcasing refined sophistication and contemporary old money style.

The comb-over is a refined hairstyle that has elegantly evolved from its traditional roots to become a modern, stylish choice for men seeking a sophisticated and contemporary look. This stylish cut features longer hair on top, meticulously combed over to one side, while the sides and back are kept shorter and evenly tapered or faded, creating a balanced and polished appearance. The modern comb-over effectively balances traditional elegance with modern old money fashion, making it a popular choice for men who want to project a confident image of contemporary sophistication and refined taste.

The Historical Evolution of the Comb Over in Old Money Fashion

The comb-over has a rich history that dates back to the early 20th century, when it was a popular choice among wealthy and influential men, reflecting its early association with upper-class style. The style’s association with old-money fashion lies in its neat, polished appearance and ability to convey sophistication and refinement, qualities highly valued in traditional old money circles.

Over the decades, the comb-over has skillfully evolved to incorporate modern elements, such as tapered sides and textured finishes, while thoughtfully maintaining its classic roots, ensuring its enduring appeal. This adaptability has allowed the comb-over to remain a timeless choice for men who appreciate the old-money aesthetic but also want to embrace contemporary styling trends, blending classic elegance with modern flair.

Ideal Hair Specifications for the Comb Over

The comb-over works best with medium to fine hair that has a slight natural wave or straight texture, providing manageability and a smooth finish. The ideal length for the hair on top is between 2-4 inches, allowing for enough length to create a smooth, swept-over look that is both stylish and functional. The sides and back should be kept shorter, usually between 0.5-2 inches, depending on the desired level of contrast and personal preference, creating a defined and contemporary silhouette. The comb-over’s volume can be customized to suit your unique face shape, ranging from a sleek, flat look to a more voluminous, textured style, offering versatility in adapting the style to individual features.

Celebrities Who Master the Comb Over Hairstyle

• George Clooney: Clooney’s classic comb-over, often styled with a side part, perfectly exemplifies the style’s timeless appeal and its inherent ability to project an image of refined sophistication, making it a signature part of his elegant look.

George Clooney Classic comb-over Hairstyle

Alt text: George Clooney, showcasing a classic comb over hairstyle, exemplifying timeless appeal and refined old money sophistication.

• Ryan Gosling: Gosling’s modern comb-over features a shorter length on the sides and a textured, volumized top, showcasing the style’s adaptability to contemporary trends, proving its relevance in modern fashion.
• Leonardo DiCaprio: DiCaprio’s comb-over, often styled with a subtle taper and side part, demonstrates the style’s versatility and its ability to complement various face shapes and personal styles, highlighting its adaptability and broad appeal.

Leonardo DiCaprio Comb Over Hairstyle

Alt text: Leonardo DiCaprio, presenting a comb over hairstyle with a subtle taper, illustrating its versatility and adaptable old money style.

Styling Techniques for the Comb Over

• Start with clean, damp hair and apply a small amount of styling cream or pomade to the hair on top, distributing it evenly with a comb or your fingers to prepare for styling.
• Using a blow dryer and a round brush, sweep the hair on top over to one side, creating volume and a smooth, polished finish, shaping the comb-over and adding lift.
• For a more textured, modern look, use a matte pomade or clay to add definition and movement to the hair on top, enhancing texture and creating a contemporary feel.
• Use a fine-toothed comb to create a neat, defined side part, and finish with a light-hold hairspray to keep the style in place throughout the day, ensuring the comb-over maintains its shape and sophistication.

Facial Hair Options for the Comb Over

The comb-over’s sophisticated, polished appearance pairs seamlessly with various facial hairstyles, offering flexibility in grooming choices. A clean-shaven face can highlight the comb over’s neat, refined look, emphasizing its clean lines and polished finish. Alternatively, a well-groomed stubble or short beard can add a touch of masculinity and texture, providing a balanced and contemporary contrast. For a more contemporary, balanced appearance, consider pairing your comb over with a neatly trimmed goatee or a well-defined mustache, which can complement the hairstyle’s blend of classic and modern elements, creating a harmonious and stylish overall look.

Recommended Hair Products for the Comb Over

To achieve and maintain the perfect comb-over, invest in high-quality styling products that offer medium to strong hold and a range of finishes to suit different styles:

• Blind Barber 90 Proof Pomade: Provides a strong, pliable hold with a moderate shine, making it ideal for creating sleek, polished combovers that require control and a refined finish.
• Hanz de Fuko Claymation: Offers a matte, textured finish with a stronghold, perfect for more modern, volumized comb-over styles that prioritize texture and a natural look.

Maintenance Schedule and Barber Visits for the Comb Over

To keep your comb sharp and well-maintained, schedule regular barber visits every 3-4 weeks to trim the sides and back and maintain the proper length on top, ensuring the comb-over retains its shape and polished appearance.

The comb-over haircut is ideal for men who want to project confidence while wearing modern old-money aesthetics infused with contemporary trends, offering a versatile and stylish option for those seeking a refined and up-to-date look.

11. The French Crop: Effortless Style with Textured Simplicity

Alt text: A man with a stylish French crop hairstyle, embodying effortless style and textured simplicity in old money grooming.

The French crop, also known as the crop top or textured crop, is a simple yet stylish hairstyle that effectively combines elements of the classic Caesar cut with modern textures and finishes, creating a versatile and contemporary look. This versatile style features short hair on the back and sides, with a slightly longer, textured top that is typically styled forward or to the side, offering flexibility in styling. The French crop’s refined simplicity and low-maintenance nature make it a popular choice for men who seek a balanced blend of classic style and contemporary charm, providing an effortless yet polished appearance.

The Classic Roots and Modern Appeal of the French Crop

While the French crop may not have a direct association with old-money fashion, its roots in the classic Caesar cut and its emphasis on simplicity align with old-money values that prioritize understated elegance and functionality. The Caesar cut, originating in ancient Rome and popularized by the Roman emperor Julius Caesar, has become a timeless, iconic hairstyle, known for its practicality and clean lines.

The French crop’s modern interpretation of this classic look, with its textured top and clean, tapered sides, reflects a harmonious balance between traditional style and contemporary preferences, making it highly versatile. This fusion of old and new makes the French crop particularly appealing to men who appreciate the elegance and refinement of old-money aesthetics but desire a more modern and manageable style, bridging classic and contemporary grooming.

Ideal Hair Versatility for the French Crop

The French crop works well with most hair types and textures, from fine to thick and straight to wavy, making it a universally flattering and adaptable hairstyle. The ideal length for the top is 1-2 inches, which allows enough hair to create a textured, slightly messy appearance, enhancing its modern appeal. The back and sides are usually kept shorter, between 0.5 and 1 inch, and can be tapered or faded for a clean, modern look, creating a defined silhouette. The French crop’s volume is typically moderate, focusing on texture rather than height, emphasizing its effortless and natural style.

Celebrities Who Sport the French Crop

• Cillian Murphy: Murphy’s French crop in “Peaky Blinders” features a longer, textured top with shaved sides, demonstrating the style’s adaptability to period dramas and modern fashion, showcasing its versatility across different eras and styles.

Cillian Murphy French Crop haircut

Alt text: Cillian Murphy, featuring a French crop haircut in “Peaky Blinders,” demonstrating its adaptability and modern old money style.

• Tom Hardy: Hardy’s French crop features a slightly longer, textured top and tapered sides, showcasing the style’s rugged, masculine appeal, highlighting its versatility and masculine charm.
• Daniel Craig: Craig’s interpretation of the French crop includes a shorter top and faded sides, creating a clean, minimalist look that perfectly complements his sharp features, emphasizing its clean lines and modern sophistication.

Styling Techniques for the French Crop

• Start with clean, damp hair and apply a small amount of sea salt spray or texturizing spray to the hair on top, distributing it evenly with your fingers to enhance texture and volume.
• Use a blow dryer on a low heat setting to dry the hair on top while simultaneously using your fingers to create a textured, tousled appearance, emphasizing the French crop’s natural and effortless style.
• Apply a small amount of matte clay or putty to the hair on top, using your fingers to define the texture and create a slightly messy, lived-in look, adding definition and a contemporary edge.
• For a more polished appearance, use a comb to style the hair on top forward or to the side, creating a neat, uniform finish, offering versatility in styling from casual to more refined looks.

Facial Hair Options for the French Crop

The French crop’s simple, versatile nature allows it to pair well with various facial hairstyles, offering flexibility in grooming choices. A clean-shaven face can highlight the crop’s neat, refined appearance, emphasizing its clean lines and simplicity. Alternatively, a well-groomed stubble or short beard can add a touch of ruggedness and masculinity, providing a balanced and contemporary contrast. For a balanced, contemporary look, consider pairing your French crop with a neatly trimmed goatee or a well-maintained 5 o’clock shadow, which can complement the hairstyle’s blend of classic simplicity and modern texture, creating a harmonious and stylish overall appearance.

Recommended Hair Products for the French Crop

To achieve and maintain the perfect French crop, invest in products that enhance texture and provide a matte, natural finish, emphasizing the style’s effortless look:

• Baxter of California Clay Pomade: Offers a pliable hold with a matte finish, ideal for creating textured, tousled French crop styles that require flexibility and a natural look.
• Triumph & Disaster Karekare Sea Salt Spray: Adds volume and texture to the hair, making it easier to achieve the French crop’s signature messy, lived-in appearance, enhancing texture and volume effortlessly.

Maintenance Schedule and Barber Visits for the French Crop

To keep your French crop looking sharp and well-defined, schedule regular barber visits every 3-4 weeks to maintain the proper length on top and neatly trim the back and sides, ensuring the crop retains its shape and style. Regular maintenance is key to keeping the French crop looking its best, reflecting a commitment to refined yet effortless grooming.

12. The Side Fringe: Youthful Energy with Textured Style

Side Fringe haircuts for men

Alt text: A man with a trendy side fringe hairstyle, embodying youthful energy and textured style in modern old money grooming.

The side fringe is a youthful, textured hairstyle that cleverly combines elements of the classic side-swept look with modern, tousled finishes, creating a contemporary and stylish appearance. This trendy style features longer hair on top swept to one side, creating a fringe that falls casually across the forehead, while the sides and back are kept shorter, and can be either evenly textured or tapered, offering versatility in the overall look. The side fringe’s casual, laid-back vibe and its ability to soften facial features make it a popular choice among younger men who want to embrace a more relaxed, contemporary aesthetic, while still nodding to classic styles.

The Modern Reinterpretation of Classic Side-Swept Styles

While the side fringe may not be directly associated with old-money fashion, its roots in the classic side-swept look and its emphasis on texture and movement align with the evolution of men’s hairstyles throughout the 20th century, adapting classic styles for modern tastes. The side-swept style has been a staple of men’s grooming since the 1940s and has continuously been adapted to incorporate modern elements and trends, ensuring its enduring appeal.

The side fringe’s contemporary interpretation of this timeless look, with its tousled texture and softer, more natural appearance, reflects a significant shift in men’s grooming preferences towards styles that prioritize ease, individuality, and self-expression, moving away from more rigid styles. While not strictly adhering to traditional old-money aesthetics, the side fringe represents a modern continuation of the classic side-swept tradition, updated for the contemporary age and appealing to a younger demographic seeking a blend of classic and modern.

Ideal Hair Specifications for the Side Fringe

The side fringe works best with medium to thick hair that has a slight natural wave or straight texture, providing the necessary volume and manageability for creating the fringe. The ideal length for the top is between 2 and 4 inches, allowing enough hair to create a substantial fringe and enabling various styling options, from casual to more styled looks. The sides and back are usually kept shorter, between 1 and 2 inches, and can be textured, tapered, or undercut for a more contemporary, edgy look, offering customization and style versatility. The side fringe’s volume is typically moderate to high, emphasizing the creation of a full, lush fringe that can be styled in various ways, from neatly side-swept to more tousled and textured, providing styling flexibility.

Celebrities Who Exemplify the Side Fringe Hairstyle

• Timothée Chalamet: Chalamet’s side fringe, often styled with a messy, textured finish, showcases the style’s ability to appear effortlessly cool and modern, perfectly embodying youthful and contemporary style.

Timothée Chalamet Side Fringe Hairstyle

Alt text: Timothée Chalamet, showcasing a side fringe hairstyle, embodying effortless cool and modern old money youthfulness.

• Harry Styles: Styles’ iconic side fringe features a longer, tousled top and textured sides, epitomizing the style’s youthful, carefree charm, making it a signature part of his contemporary look.
• Cole Sprouse: Sprouse’s side fringe, with a shorter length and a more polished finish, demonstrates the style’s versatility and potential for a neater, more refined appearance, highlighting its adaptability and styling flexibility.

Styling Techniques for the Side Fringe

• Start with clean, damp hair and apply a small amount of volumizing mousse or sea salt spray to the hair on top, distributing it evenly with your fingers to enhance volume and texture for styling.
• Use a blow dryer to dry the hair on top while using a round brush to sweep the hair to the side and create volume at the roots, shaping the side fringe and adding lift.
• Apply a small amount of matte pomade or styling cream to the hair on top, using your fingers to define the fringe and create a textured, piece-y appearance, enhancing texture and definition for a modern look.
• For a more relaxed, tousled look, use your fingers to gently mess up the fringe and add a carefree, lived-in vibe, achieving an effortless and casual style.

Facial Hair Options for the Side Fringe

The side fringe’s youthful, laid-back appearance pairs well with various facial hairstyles, particularly those emphasizing a fresh and contemporary look. A clean-shaven face can highlight the side fringe’s soft, textured appearance and keep the focus on the hair, emphasizing its youthful vibe. For a more balanced, contemporary look, consider pairing your side fringe with a light stubble or a short, well-groomed beard, which can add a touch of maturity and masculinity without overwhelming the hairstyle’s casual, effortless charm, creating a harmonious and stylish overall appearance.

Recommended Hair Products for the Side Fringe

To achieve and maintain the perfect side fringe, invest in products that enhance volume, texture, and movement, emphasizing the style’s effortless and casual nature:

• Bumble and Bumble Surf Spray: A saltwater-based spray that adds texture, volume, and a matte finish to the hair, making it easier to achieve the side fringe’s signature tousled appearance, enhancing texture and volume effortlessly.
• Hanz de Fuko Scheme Cream: A lightweight, versatile styling cream that provides a soft, pliable hold with a natural finish, perfect for creating a smooth, defined fringe that retains a natural look and feel.

Maintenance Schedule and Barber Visits for the Side Fringe

To keep your side fringe looking fresh and well-defined, schedule regular barber visits every 4-6 weeks to maintain the proper length on top and neatly trim the sides and back, ensuring the fringe retains its shape and style. Regular maintenance is key to keeping the side fringe looking its best, reflecting a commitment to a youthful and contemporary grooming style.

13. The Regulation Cut: Military Precision and Disciplined Style

Regulation Cut Men

Alt text: A man with a sharp regulation cut hairstyle, embodying military precision and disciplined old money grooming.

The regulation cut, also known as the high and tight or the military cut, is a clean, precise hairstyle that strictly adheres to the grooming standards of the armed forces, emphasizing order and discipline. This no-nonsense look features short hair on the sides and back, often buzzed down to the skin, with slightly longer hair on top, usually no more than an inch long, creating a sharp and uniform appearance. The regulation cut’s sharp, disciplined appearance and its strong association with military tradition make it particularly popular among men who value order, efficiency, and a neat, put-together look, projecting an image of precision and control.

The Military Heritage and Disciplined Aesthetics of the Regulation Cut

While the regulation cut may not be directly associated with traditional old-money fashion, its deep roots in military tradition and its strong emphasis on discipline, order, and cleanliness align closely with certain old-money values that prioritize functionality and understated rigor. The military has long been associated with the upper echelons of society, with many wealthy and influential families historically sending their sons to serve in the armed forces as both a rite of passage and a mark of social status, reinforcing the link between military service and upper-class traditions.

Regulation Cut Military History

Alt text: Historical image of men with regulation cut hairstyles in military settings, illustrating its origins and disciplined old money associations.

The regulation cut’s strict adherence to grooming standards and its projection of a neat, put-together appearance directly reflect the importance placed on self-discipline and presentability within old-money circles, where understated elegance and attention to detail are highly valued. By embracing the regulation cut, men can effectively tap into this rich tradition of military precision and the associated values of order, efficiency, and respectability, subtly conveying a sense of disciplined and refined style.

Ideal Hair Specifications for the Regulation Cut

The regulation cut works effectively with most hair types and textures, as the short length and high-and-tight style minimize the impact of individual hair characteristics, making it universally adaptable. The ideal length for the top is between 0.5 and 1 inch, while the sides and back are usually buzzed down to a uniform length of 1/8 inch or less, creating a sharp and clean contrast. Due to its extremely short length, the regulation cut has minimal volume and is characterized by a flat, close-to-the-head appearance, emphasizing its practicality and neatness. The lack of volume significantly contributes to the style’s neat, disciplined look and low-maintenance nature, making it a highly functional and straightforward grooming choice.

Celebrities Who Sport the Regulation Cut

• Jake Gyllenhaal: Gyllenhaal’s regulation cut in the movie “Jarhead” vividly showcases the style’s strong association with military culture and its inherent ability to project a tough, masculine appearance, making it iconic in military portrayals.

Jake Gyllenhaal Regulation Cut

Alt text: Jake Gyllenhaal in “Jarhead,” sporting a regulation cut, emphasizing its military association and tough old money masculinity.

• Tom Hardy: Hardy’s haircut in the film “Warrior” skillfully demonstrates the style’s versatility and its potential to complement a muscular, athletic physique, highlighting its adaptability across different looks and body types.
• Justin Timberlake: Timberlake’s regulation cut during his early solo career notably highlighted the style’s clean, sharp appearance and its ability to convey a strong sense of discipline and focus, making it a stylish and purposeful choice.

Styling Techniques for the Regulation Cut

• Due to the regulation cut’s extremely short length, styling is typically minimal and primarily focused on maintaining the hair’s neat, uniform appearance, emphasizing its low-maintenance appeal.
• For a polished look, apply a small amount of matte pomade or wax to the hair on top and use your fingers to distribute the product evenly and create a smooth, tidier appearance, enhancing the regulation cut’s clean and sharp aesthetic.

Facial Hair Options for the Regulation Cut

The regulation cut’s clean, disciplined appearance is best complemented by a clean-shaven face, reinforcing the style’s strong association with military precision and strict adherence to grooming standards, creating a cohesive and sharp look. However, for those who prefer facial hair, a well-maintained, short stubble can work harmoniously with the regulation cut, provided that it is kept exceptionally neat and tidy to avoid detracting from the hairstyle’s sharp, put-together look, maintaining a disciplined and refined overall appearance.

Recommended Hair Products for the Regulation Cut

Given the regulation cut’s extremely short length and low-maintenance nature, minimal product is generally needed to maintain the style, highlighting its practicality and ease of care. However, the following products can be beneficial in helping to keep the hair looking clean, healthy, and well-groomed:

• American Crew Fiber: Is a matte-finish, high-hold product that can help to add texture and definition to the short hair on top, providing subtle styling and control when desired.
• Baxter of California Super Close Shave Formula: Is a soothing, lubricating shave cream that can help to ensure a smooth, irritation-free shave when maintaining the regulation cut’s clean, close-cropped appearance, essential for keeping the style sharp and neat.

Maintenance Schedule and Barber Visits for the Regulation Cut

Frequent barber visits are absolutely essential to maintaining the precise, uniform appearance of the regulation cut, ensuring it remains sharp and well-defined. Schedule appointments every 1-2 weeks to keep the sides and back closely cropped and the top meticulously trimmed to the desired length, upholding its military precision. Between visits, wash the hair regularly with a gentle shampoo to keep the scalp clean and healthy, and use a moisturizing conditioner to prevent dryness and irritation, promoting overall scalp and hair health for a consistently sharp and disciplined look.

14. The Short Curtain: Retro Revival with Effortless Cool

Short Curtain

Alt text: A man with a stylish short curtain hairstyle, embodying retro revival and effortless cool in contemporary old money style.

The short curtain hairstyle is a retro-inspired look that has recently made a significant return to men’s fashion, capturing a blend of nostalgia and modern style. This stylish, low-maintenance cut features short hair on the sides and back, with slightly longer hair on top that is neatly parted in the middle and allowed to fall naturally to either side, elegantly resembling a curtain, hence its name. The short curtain’s vintage charm and its ability to seamlessly blend classic and contemporary elements make it a particularly popular choice among fashion-forward men who appreciate a touch of nostalgia in their personal style, while still maintaining a modern edge.

The 90s Nostalgia and Effortless Style of the Short Curtain

The short curtain hairstyle notably originated in the 1990s and reached its peak popularity thanks to influential celebrities like Leonardo DiCaprio and Johnny Depp, who significantly popularized this iconic 90s look.

Leonardo DiCaprio and Johnny Depp Short Curtain Hair 90s

Alt text: Black and white photo of Leonardo DiCaprio and Johnny Depp with short curtain hairstyles in the 90s, icons of retro old money cool.

While the look may not be directly associated with traditional old-money fashion, the short curtain’s revival in recent years accurately reflects a broader cultural trend of nostalgia and a renewed appreciation for vintage hairstyles from past decades. The short curtain’s unique blend of classic and contemporary features, its low-maintenance nature, and its inherent effortless cool factor align seamlessly with the old-money aesthetic’s emphasis on timeless style, understated elegance, and a certain nonchalance, making it a subtly sophisticated choice.

Ideal Hair Specifications for the Short Curtain

The short curtain hairstyle works best with straight to slightly wavy hair that has a medium to fine texture, providing the right balance of manageability and natural fall. The ideal length for the top is between 2 and 4 inches, allowing enough hair to create the signature curtain-like part and fall naturally and gracefully to either side of the face. The sides and back are usually kept shorter, between 1 and 2 inches, to create a subtle contrast and effectively emphasize the curtain effect on top, highlighting the central part. The short curtain’s volume is typically moderate, focusing primarily on maintaining a natural, effortless appearance rather than creating excessive height or fullness, emphasizing its relaxed and understated style.

Celebrities Who Revived the Short Curtain Haircut

• Timothée Chalamet: Chalamet’s short curtain hairstyle has become a signature look for the young actor, perfectly showcasing the style’s youthful, carefree charm and its versatile ability to complement various fashion choices, making it a modern style icon.
• Charles Melton: Melton’s contemporary interpretation of the short curtain features a slightly longer top and a more tousled, textured finish, effectively demonstrating the style’s versatility and potential for personal customization, adapting it for modern tastes.

Charles Melton Short Curtain Hairstyle

Alt text: Charles Melton, showcasing a short curtain hairstyle with a tousled finish, demonstrating its versatility and contemporary old money style.

• Patrick Schwarzenegger: Schwarzenegger’s short curtain, often styled with a side part and a polished finish, distinctly highlights the style’s ability to appear both laid-back and put-together, depending on the specific styling techniques used, offering flexibility in its presentation.

Styling Techniques for the Short Curtain

• Start with clean, damp hair and apply a small amount of lightweight, moisturizing hair cream or serum to the hair on top, distributing it evenly with your fingers to hydrate and prepare the hair for styling.
• Using a comb, create a distinct middle part, ensuring that the hair naturally falls to either side of the part, defining the signature curtain look.
• Allow the hair to air dry naturally for a truly effortless look, or use a blow dryer on a low heat setting to gently encourage the hair to fall in the desired direction, enhancing the curtain effect.
• For a more polished appearance, use a small amount of pomade or wax to define the part and add a subtle shine, carefully avoiding disrupting the hair’s natural fall, maintaining its relaxed and graceful style.

Facial Hair Options for the Short Curtain

The short curtain hairstyle’s inherently laid-back, youthful appearance pairs most effectively with clean-shaven faces, which helps to maintain the primary focus on the hair and its unique parted style, emphasizing its relaxed and youthful vibe. However, for those who prefer facial hair, a light stubble or a short, well-groomed beard can harmoniously work with the short curtain, adding a touch of maturity and masculinity to the overall look, while still complementing the hairstyle’s effortless charm. The key is to ensure that any facial hair is kept exceptionally neat and trimmed to avoid overwhelming the hairstyle’s effortless, natural vibe, maintaining a balanced and stylish appearance.

Recommended Hair Products for the Short Curtain

To achieve and maintain the perfect short curtain hairstyle, consider using the following recommended products that enhance the hair’s natural texture and promote a relaxed, effortless style:

• Malin + Goetz Sage Styling Cream: Is a lightweight, moisturizing cream that provides a soft, natural hold and enhances the hair’s texture and shine, perfect for creating a relaxed and subtly styled short curtain.
• Aesop Violet Leaf Hair Balm: Is a nourishing, non-greasy balm that effectively helps to tame frizz, add definition, and protect the hair from environmental stressors, ensuring the short curtain remains smooth and naturally styled.

Maintenance Schedule and Barber Visits for the Short Curtain

To keep your short curtain hairstyle looking consistently fresh and well-maintained, schedule regular barber visits every 4-6 weeks to trim the sides and back and keep the top at the desired length, ensuring the curtain shape remains defined and stylish. Between appointments, wash your hair with a gentle, sulfate-free shampoo and conditioner to maintain the hair’s natural moisture and prevent damage, promoting overall hair health. Style as needed using lightweight, non-greasy products that enhance the hair’s natural texture and fall, maintaining the short curtain’s effortless and relaxed style with minimal daily effort.

15. The Edgar Haircut: Edgy Modernity with Bold Angularity

15 Old Money Hairstyles Curated for Gents Who Want to Look Rich

Alt text: A man with a bold Edgar haircut, embodying edgy modernity and sharp angularity in contemporary old money style.

The Edgar haircut, also known as the “South of France” haircut, is a modern, edgy style that has recently gained significant popularity, particularly among younger men seeking a bold and contemporary look. This distinctive haircut is characterized by its short, often faded sides and back, which sharply contrast with a longer, textured top that is typically styled forward or upward to create a sharp, angular fringe across the forehead. The Edgar’s uniquely distinctive silhouette and its close association with contemporary fashion trends make it a favored choice among younger men who want to make a strong stylish statement and stand out from the crowd with a cutting-edge hairstyle.

The Contemporary Edge of the Edgar Cut in Modern Style

While the Edgar haircut does not directly relate to traditional old-money fashion or historical contexts, its undeniably modern, edgy appearance represents a notable departure from the more traditional, conservative hairstyles that are often associated with classic old-money aesthetics. However, the Edgar’s inherent emphasis on precision cutting, clean lines, and bold styling can be effectively seen as a contemporary interpretation of the meticulous attention to detail and high grooming standards that are typically valued in traditional old money circles, albeit with a modern twist.

Edgar-style haircuts distinctly allow men to confidently demonstrate self-expression and a willingness to take risks in their style choices, qualities that are consistently admired in fashion-forward individuals, regardless of their background or social status, making it a bold and confident style statement.

Ideal Hair Specifications for the Edgar Haircut

The Edgar haircut works most effectively with straight to slightly wavy hair that has a medium to thick texture, providing the necessary body and manageability for achieving its signature angular and textured look. The ideal length for the top is between 2 and 4 inches, allowing enough hair to create the signature angular fringe and textured, voluminous style that defines the Edgar cut. The sides and back are usually faded or undercut, with the hair length gradually decreasing from the top to the bottom, creating a sharp, contemporary contrast that enhances the angular fringe. Edgar’s volume is typically high, focusing on creating a bold, attention-grabbing silhouette that distinctly emphasizes the angular lines and textured finish of the hair on top, making it a visually striking and modern hairstyle.

Celebrities Who Sport the Edgar Haircut

• Kylian Mbappé: Mbappé, the renowned French professional footballer, has notably sported a sleek, exceptionally well-defined Edgar haircut, effectively showcasing the style’s sporty, youthful appeal and its inherent potential for precision styling, making it a popular choice in sports and fashion.

Kylian Mbappé Edgar Hairstyle

Alt text: Kylian Mbappé, the football star, showcasing a sleek Edgar hairstyle, exemplifying sporty youthfulness in modern old money style.

• Anwar Hadid: Hadid, the prominent model and younger brother of Gigi and Bella Hadid, has frequently been seen with a tousled, textured Edgar cut that clearly demonstrates the style’s edgy, fashion-forward vibe, highlighting its appeal in high fashion circles.

Anwar Hadid Edgar Hairstyle

Alt text: Anwar Hadid, a fashion model, sporting a textured Edgar hairstyle, illustrating its edgy and fashion-forward old money appeal.

• Odell Beckham Jr.: Beckham Jr., the American football player, has famously worn a boldly styled Edgar haircut with distinctive blonde highlights, perfectly exemplifying the style’s significant potential for creative customization and self-expression, making it a standout choice for personal style.

Styling Techniques for the Edgar Haircut

• Start with clean, damp hair and apply a small amount of high-hold styling gel or pomade to the hair on top, distributing it evenly with your fingers to prepare for styling and ensure maximum hold.
• Using a comb or your fingers, style the hair on top directly forward or slightly upward, creating a sharp, angular fringe that typically falls just above the eyebrows, defining the Edgar’s signature fringe.
• Use a blow dryer on high heat to effectively lock the style firmly in place, directing the airflow predominantly upward and forward to further emphasize the angular shape and texture of the fringe, enhancing its dramatic effect.
• For a more voluminous, textured look, use a small amount of matte clay or putty to define individual hair strands and create a slightly messy, edgy finish, adding depth and contemporary flair to the Edgar cut.

Facial Hair Options for the Edgar Haircut

The Edgar haircut’s inherently bold, contemporary appearance is often paired most effectively with clean-shaven faces, which helps to maintain the primary focus directly on the hair’s sharp lines and angular styling, emphasizing its modern aesthetic. However, for those who prefer facial hair, a well-groomed, precisely shaped beard or goatee can work harmoniously with the Edgar cut, adding an extra layer of dimension and unique personal style to the overall look, while still maintaining its edgy vibe. The key is to ensure that the facial hair is always precisely trimmed and effectively complements the clean, defined lines of the haircut, creating a cohesive and stylish appearance.

Recommended Hair Products for the Edgar Haircut

To achieve and consistently maintain the perfect Edgar haircut, consider using the following highly recommended products that are specifically designed to enhance its angular shape and textured finish:

• Hanz de Fuko Heavymade Pomade: Is a high-hold, water-based pomade with an exceptionally strong, long-lasting hold and a natural, satin finish, making it ideally suited for creating sharp, angular styles like the Edgar cut that demand maximum control.
• Layrite Cement Matte Hair Clay: Is a pliable, matte-finish clay that provides a strong, texturizing hold, making it perfectly suited for achieving the Edgar’s signature disheveled, edgy look, while maintaining its angular shape and textured style.

Maintenance Schedule and Barber Visits for the Edgar Haircut

Frequent barber visits are absolutely essential to properly maintain the Edgar haircut’s precise, angular appearance, ensuring it remains sharp and well-defined. Schedule regular appointments every 2-3 weeks to keep the sides and back consistently faded or undercut and the top meticulously trimmed to the desired length and shape, upholding its distinctive silhouette. Use lightweight, water-based styling products daily to restyle the hair as needed, ensuring that the angular fringe and textured finish remain perfectly intact throughout the day, maintaining the Edgar’s bold and contemporary style.

What’s the Right Hairstyle for Me? Tailoring Your Look

Choosing the perfect old-money hairstyle for you is a deeply personal decision that involves carefully considering several key factors, most notably your unique facial features, lifestyle demands, personal fashion style, and age appropriateness. Each of these elements plays a critical role in ensuring that your chosen hairstyle not only looks stylish but also harmonizes with your overall image and personal brand.

This comprehensive section will thoroughly explore each of these essential factors in detail, providing expert guidance on how to effectively match different old-money hairstyles to various face shapes and age groups, ensuring you make the most informed and flattering choice for your individual needs and preferences.

Old Money style grooming and hair

Alt text: A curated selection of old money style grooming and hair products, highlighting the essential elements of refined men’s care.

Face Shape Harmony: Finding Your Most Flattering Style

Understanding your face shape is absolutely crucial when you are choosing a hairstyle that not only flatters your natural features but also significantly enhances your overall appearance, ensuring a harmonious and balanced look. If you are unsure of your face shape, you can easily determine it by using this simple and quick quiz designed to help you identify your face shape accurately.

The main face shapes that are commonly recognized include:

Oval Face Shape

An oval face shape is typically characterized by a length that is slightly longer than its width, featuring a gently rounded jawline and a forehead that is just slightly wider than the chin, creating balanced proportions. Most hairstyles work exceptionally well with this inherently versatile face shape, giving you significant flexibility in your style choices. When selecting a hairstyle, focus primarily on styles that effectively maintain the face’s natural balance and harmonious proportions, rather than trying to alter its shape, to enhance your natural features.

Round Face Shape

A round face shape is defined by dimensions that are nearly equal in both length and width, characterized by a soft, curved jawline and a notable absence of prominent angles, resulting in a softer facial appearance. For round face shapes, it is generally recommended to opt for hairstyles that strategically add height and volume on the top of the head, while simultaneously keeping the sides and back relatively short and close to the head. This styling approach effectively works to elongate the face visually and create a more angular and defined appearance, counteracting the natural roundness.

Square Face Shape

A square face shape is distinctly defined by a strong, angular jawline and a forehead that is approximately the same width as the chin, creating a bold and structured facial appearance. When choosing hairstyles for a square face shape, prioritize styles that effectively soften the naturally strong angles of the jawline to create a more balanced look. Styles that typically work well include those with shorter sides paired with a slightly longer, textured top, which helps to soften the squareness and add a touch of gentleness to the overall facial structure.

Heart Face Shape

A heart face shape is characterized by being wider at the forehead and cheekbones, and then gradually narrowing down to a distinctly pointed chin, creating a heart-like silhouette. Select hairstyles that are specifically designed to balance the wider forehead and the narrower chin that are characteristic of a heart face shape. Styles that often work best include those with side-swept fringes or a medium-length top combined with shorter sides. These styles effectively help to add visual width to the narrower chin area while simultaneously minimizing the width of the broader forehead, creating a more balanced and harmonious facial appearance.

Diamond Face Shape

A diamond face shape is uniquely characterized by being widest at the cheekbones, with a notably narrower forehead and chin, and often features a pointed jawline, creating a distinctive diamond-like facial structure. For diamond face shapes, it is generally recommended to pick hairstyles that strategically add volume and width specifically at both the chin and forehead areas. At the same time, it is advisable to keep the hair relatively close to the head at the cheekbones to effectively minimize width in this area. This styling approach helps to create a more balanced and proportional facial silhouette, counteracting the diamond shape’s natural narrowness at the forehead and chin.

Hair Type and Texture: Choosing Styles That Work For You

Your individual hair type and texture are critical determinants in selecting which old-money hairstyles will work best for you, ensuring the style is both achievable and flattering. The main hair types that are typically considered include:

Straight Hair

Straight hair is naturally characterized by its smooth and flat nature, with no discernible curl or wave from root to tip, making it very sleek. Most old-money hairstyles are particularly well-suited for straight hair, making it significantly easier to achieve a sleek, polished appearance that is often desired in these classic styles. When styling straight hair, focus on styles that strategically add volume and texture to prevent the hair from appearing flat or lifeless, ensuring it maintains body and movement.

Wavy Hair

Wavy hair naturally falls in loose, soft S-shaped curves that are more defined than straight hair but less tightly coiled than curly hair, offering a gentle wave pattern. Embrace your hair’s natural texture by thoughtfully choosing styles that effectively enhance the waves, such as the classic side part or the short curtain, which complement natural waves. Use lightweight, moisturizing hair products to define and control the waves without weighing them down, maintaining their natural bounce and shape.

Curly Hair

Curly hair is characterized by forming tight, defined ringlets or coils that naturally spring from the scalp to the ends, creating a voluminous and textured look. Opt for old-money hairstyles that are specifically designed to work seamlessly with your natural curl pattern, such as the French crop or the regulation cut, which accommodate curls well. Use specialized hair products that provide ample moisture, curl definition, and effective frizz control to manage curly hair, and consider using a diffuser attachment when blow-drying your hair to maintain the integrity and shape of the curls, preventing frizz and enhancing definition.

Kinky/Coily Hair

Kinky or coily hair is distinguished by very tight, densely packed curls or coils that may exhibit a zig-zag or Z-shaped pattern, making it highly textured and voluminous. Select hairstyles that genuinely embrace your hair’s natural texture and coil pattern, such as the buzz cut or a short, tapered afro, which celebrate natural hair. Use deeply moisturizing and nourishing hair products to keep kinky/coily hair adequately hydrated, healthy, and defined, and consider incorporating protective styling techniques to minimize potential damage and effectively maintain the hair’s natural pattern and health.

Lifestyle and Maintenance: Balancing Style with Practicality

When you are making a decision about choosing an old-money hairstyle, it is essential to thoughtfully consider your lifestyle and the level of daily maintenance you are genuinely willing to commit to, ensuring the hairstyle fits seamlessly into your routine. Certain hairstyles, particularly those requiring intricate styling, may demand frequent trims to maintain their shape, daily styling routines using specific products, and more time investment overall. In contrast, other hairstyles are inherently more low-maintenance and can be easily managed with minimal daily effort and less frequent barber visits.

If you lead a particularly busy lifestyle or simply prefer a more low-key approach to personal grooming, it is generally advisable to opt for old-money hairstyles that are known to be simple, versatile, and relatively easy to maintain, such as:

• The Buzz Cut
• The Crew Cut
• The French Crop
• The Regulation Cut

These specific styles typically require less frequent visits to the barber to maintain their shape and can be quickly and easily styled each day with minimal hair product, making them ideally suited for individuals who highly value simplicity, efficiency, and a straightforward grooming routine.

On the other hand, if you genuinely enjoy dedicating time to your personal grooming routine and appreciate the process of styling your hair each day, you might want to consider old-money hairstyles that offer significantly more opportunities for customization and personal experimentation, such as:

• The Classic Side Part
• The Slick Back
• The Quiff
• The Classic Pompadour

These more elaborate styles often require more frequent professional trims to maintain their shape, a daily styling regimen that involves specific hair products, and a greater investment of time and effort each day to achieve the desired polished look. However, these styles also afford you a much greater degree of personal self-expression and can be skillfully adapted to suit various occasions, from casual everyday events to more formal settings, and personal styling preferences, offering versatility and style flexibility.

Old-Money Hairstyles by Age Groups: Tailoring Style to Maturity

While old-money hairstyles are inherently timeless and can be stylishly worn by men across all age groups, it is important to recognize that certain hairstyles may be generally perceived as being more naturally suitable for specific age ranges. Therefore, it is often beneficial to adjust your hairstyle choice accordingly to ensure it complements your current stage of life and projects the appropriate image.

Younger Men (18-30): Embracing Contemporary Classics

Younger men typically enjoy the greatest flexibility when it comes to experimenting with various old-money hairstyles, as they can often confidently pull off bolder, more contemporary interpretations of classic looks without appearing out of place or overly styled.

Some specific styles that tend to work particularly well for this younger age group include:

• The Quiff
• The Undercut
• The French Crop
• The Short Curtain

These selected styles effectively offer a harmonious balance of classic sophistication and a modern edge, allowing younger men to express their individuality and contemporary style preferences while still thoughtfully adhering to the timeless principles of the traditional old-money aesthetic, bridging classic and modern grooming.

Middle-Aged Men (31-50): Projecting Refinement and Success

For middle-aged men, the primary focus when choosing an old-money hairstyle should be on selecting styles that effectively convey maturity, established refinement, and a strong sense of personal and professional success.

Some specific styles that are particularly well-suited for this age group include:

• The Classic Side Part
• The Taper Fade
• The Ivy League
• The Comb Over

These classic hairstyles offer a consistently polished, sophisticated appearance that is appropriately well-suited to both professional work environments and diverse social settings, while still providing ample scope for personal style expression and subtle customization to reflect individual preferences and features.

Older Men (51+): Timeless Elegance and Distinguished Grace

For older men, the key consideration when choosing an old-money hairstyle is to select styles that are not only age-appropriate but also inherently flattering and, importantly, easy to maintain on a daily basis, ensuring practicality and style.

Some styles that typically work exceptionally well for this age group include:

• The Ivy League
• The Regulation Cut
• The Classic Side Part (with a slightly longer top for added fullness)
• The Short Crew Cut

These timeless hairstyles offer a distinguished and inherently elegant appearance that gracefully embraces the natural changes in hair texture and density that often come with age, such as thinning or graying, while still consistently projecting an enduring air of refinement and understated sophistication, maintaining a polished and age-appropriate look.

Final Thoughts: Embodying Timeless Style

The old money aesthetic, traditionally associated with the upper echelons of society, inherently displays a confident and understated look that is firmly built on deeply rooted traditional values and a sense of silent, assured wealth, emphasizing subtlety over ostentation. In today’s dynamic world of fast fashion trends and often overt new money statements, the old-money aesthetic remains a steadfast bastion of enduring refinement that consistently conveys both personal excellence and quiet self-assurance, valuing substance over show.

An impeccably chosen old-money hairstyle is absolutely central to effectively achieving this distinguished and sophisticated look, and it stands out as one of the fastest and most cost-effective ways to create a lasting image of timeless elegance, refined sophistication, and a rich, understated heritage, enhancing overall style and presence.

The true key to selecting the right old-money hairstyle that is perfect for you lies in thoughtfully considering your unique personal features, your everyday lifestyle demands, and your individual personal preferences, and ultimately choosing a style that makes you feel genuinely confident, exceptionally comfortable, and authentically true to yourself. By taking the necessary time to fully understand all of the key factors involved in hairstyle selection and by patiently experimenting with different available options, you can successfully find the perfect old-money hairstyle that not only complements your unique personal style but also significantly helps you to consistently project the timeless, sophisticated image that is so closely associated with this enduring and highly respected aesthetic, ensuring a polished and refined personal brand.

Style Like a True Gentleman: Beyond the Haircut

Before we conclude, here’s one of the best-kept secrets within men’s styling circles, a valuable insight that only a select few expert image consultants truly know or are willing to openly share with their clients. First and foremost, truly professional styling fundamentally requires a deep understanding of knowing your unique body shape and your individual seasonal color palette—these are paramount factors in effectively choosing perfectly fitting clothes in colors that genuinely complement your specific skin tone, eye color, and hair color, creating a harmonious and flattering look.

Only then can a skilled stylist effectively engage in detailed styling by occasion, location, season, and even time of day, carefully selecting garments, footwear, and accessories from stylistically relevant heritage fashion brands to accurately depict an image of high personal confidence and genuine success, ensuring a consistently polished and impactful appearance.

The best part about this approach? You can easily discover your body shape, seasonal color palette, and ideal personal fashion style in less than just 5 minutes, and completely for free, thanks to our simple four-step process:

1. Find Your Body Shape: The Foundation of Fit

Different types of garments naturally flatter different body silhouettes, so accurately knowing your body shape is the essential first step in dressing like a truly confident and well-styled man, ensuring your clothes fit and enhance your physique. To quickly and easily find out your unique body shape, simply take our free body shape quiz specifically designed for men. Once you have identified your unique body shape, proceed to the second free quiz to discover your ideal and most flattering color palette.

2. Find Your Unique Color Palette: Colors That Complement You

Always remember that the various garments that compose your overall outfits come in a vast array of colors, and it is absolutely crucial to ensure that each color you choose effectively complements your natural coloring, enhancing your features. To achieve this color harmony, you must first identify your personal seasonal color palette, which you can easily determine by taking our comprehensive free seasonal color quiz specifically for men.

3. Find Your Ideal Fashion Style: Defining Your Personal Brand

By this point, you should already have a clear understanding of your body shape and your unique color palette; the next essential step is to discover your ideal personal fashion style, which truly reflects your personality and preferences. The fastest and simplest method to achieve this is to take our highly effective free fashion style quiz designed for men; this quiz will provide you with insights into your ideal style, personalized outfit ideas, relevant fashion brands that align with your style, and much more valuable information to refine your wardrobe.

4. Professional Image Consultancy with The VOU: Elevate Your Style

And if your goal is to style yourself with the expertise of a professional, perfectly tailored to each specific occasion, location, season, and time of day, you can always confidently ask our team of expert image consultants and professional fashion stylists for personalized guidance and support. Our comprehensive styling services specifically for men are recognized as being among the most thorough and detailed services available on the market today, backed by leading industry stylists who will expertly guide you step by step in creating sophisticated and impactful looks that effectively communicate affluence, inherent elegance, and a history of endless accomplishments, enhancing your personal and professional image.

Remember, simply wearing luxury brands is definitely not enough to achieve true style; to genuinely look stylish, project unwavering confidence, and convey resounding success, you must first thoroughly understand your body shape, your personal color palette, and your ideal personal style, and only then can you effectively style yourself appropriately for each specific occasion, location, season, and time of day, ensuring a consistently polished and impactful appearance.

Contact us today to save yourself unnecessary headaches, valuable time, and significant money in the long run—it’s truly time to start dressing like a confident, successful gentleman who possesses exquisite fashion taste and a refined sense of style—your initial styling assessment is completely on us as a complimentary introduction to our services!

Ru Amiri

With extensive years of expertise in high-end fashion collaborations and a PhD in Sustainable Fashion, Ru Amiri specializes in thoughtfully curating eco-conscious luxury wardrobes specifically for the modern gentleman who seeks understated refinement and sustainable style.

Laurenti Arnault

With over twenty years of direct experience in front-row fashion shows and styling events, collaborations with prestigious haute-couture houses, and a PhD in Luxury Fashion, Laurenti Arnault is a recognized expert in expertly crafting personalized looks that accurately depict classic old-money sophistication and timeless elegance.