The Old Money Hairstyle: Timeless & Sophisticated Looks for Men

The most sought-after Old Money Hairstyles encompass the Classic Side Part, the effortlessly cool Slick Back, and the scholarly chic Ivy League cut. Historically, these hairstyles were hallmarks of upper-class refinement. Today, these haircuts for men continue to emphasize clean lines, meticulous grooming, and a timeless appeal, subtly projecting an aura of wealth and sophistication.

Key Considerations for Choosing Your Old Money Hairstyle

• Face Shape and Hair Texture Harmony: Select a style that naturally complements your unique face shape and hair texture for the most flattering result.
• Lifestyle and Upkeep Commitment: Reflect on your daily routine and the time you’re willing to dedicate to maintaining your chosen hairstyle.
• Age-Appropriate Elegance: Opt for styles that not only resonate with your personal taste but also enhance your overall appearance in an age-appropriate manner.

Eager to delve deeper? Continue reading to explore the full spectrum of Old Money hairstyles ↓

1. The Classic Side Part Hairstyle for Men

Classic Side Part Old Money Hairstyle

Alt text: Men’s classic side part hairstyle, an old money look, showcasing clean lines and sophisticated grooming.

The quintessential classic side part is a hallmark of timeless men’s style. It’s defined by a sharp, distinct part that neatly divides the hair, typically extending from the crown towards the temple. In this style, the hair on top is left slightly longer than the sides, which are expertly tapered or faded to achieve a polished, clean-cut aesthetic.

The Enduring Allure of the Classic Side Part as an Old Money Look

The Classic Side Part hairstyle rose to prominence in the roaring 1920s and sophisticated 1930s. It was embraced by iconic Hollywood figures such as Cary Grant and Fred Astaire. This marked a shift from the longer, slicked-back styles of previous eras and quickly became a powerful symbol of refined masculinity.

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

Alt text: Iconic old money hairstyle inspiration from Cary Grant and Fred Astaire, both sporting the classic side part.

From left to right: Cary Grant and Fred Astaire exemplify the classic side-part hairstyle. The clean lines and structured form of the Classic Side Part inherently communicate order and discipline, core values deeply embedded within the old-money style.

Optimal Hair Texture, Length, and Volume for the Classic Side Part

The Classic Side Part hairstyle is most effective with medium to fine hair textures that possess a slight natural wave. The hair on top should be sufficiently long to allow for combing and maintaining the defined part, typically around 2 to 4 inches. The sides are kept shorter, ideally between 0.5 and 1 inch. The aim is to achieve a balanced volume that upholds the style’s structured integrity without appearing overly rigid or heavy.

Celebrities Renowned for the Classic Side Haircut

• Jon Hamm: His portrayal of Don Draper in “Mad Men” has cemented the Classic Side Part as a modern style benchmark.

Jon Hamm Classic Side Part Old Money Hairstyle

Alt text: Jon Hamm in Mad Men, showcasing the timeless classic side part hairstyle associated with old money elegance.

Jon Hamm’s classic side part hairstyle in Mad Men.

• George Clooney: Clooney’s side-parted silver fox hair is a celebrated example of the classic side part as an old money hairstyle.

George Clooney Classic Side Part Old Money Hairstyle

Alt text: George Clooney’s distinguished silver fox classic side part hairstyle, embodying old money sophistication.

George Clooney’s silver fox classic side part hairstyle.

• David Beckham: This British soccer icon has showcased various takes on the Classic Side Part, demonstrating its enduring versatility.

David Beckham Classic Side Part Old Money Hairstyle

Alt text: David Beckham’s contemporary classic side part hairstyle, a modern iteration of old money style.

David Beckham’s modern iteration of the classic side part Old Money hairstyle.

• Ryan Gosling: Gosling’s interpretation of the side part includes a slightly longer top and a more relaxed, textured finish.

Ryan Gosling Classic Side Part Old Money Hairstyle

Alt text: Ryan Gosling’s relaxed classic side part hairstyle, a textured and modern approach to old money hair.

Ryan Gosling’s classic side part hairstyle.

Expert Styling Techniques for the Classic Side Part

• Begin with hair that is damp, having been towel-dried. Apply a small amount of pomade or styling cream, focusing on distributing it from the roots to the tips.
• Utilize a fine-toothed comb to create a crisp, well-defined part. Start from the crown and proceed towards the temple.
• Blow-dry the hair on top in the direction of the part. Employ a round brush to introduce volume and ensure a smooth finish.
• For a more casual look, use your fingers to gently tousle the hair on top, being careful to maintain the structure of the part.

Facial Hairstyle Pairings

The Classic Side Part is ideally paired with a clean-shaven face, which accentuates the sharp, polished aesthetic. However, a well-groomed mustache or a neatly trimmed beard can also effectively complement this hairstyle, adding either 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 a medium to firm hold and a subtle sheen. Baxter of California’s Hard Water Pomade or Creed’s Green Irish Tweed Hair Pomade are excellent choices. For added hold and to control frizz, consider a lightweight hair spray like R+Co’s Outer Space Flexible Hairspray.

Maintenance and Barber Visits

To preserve the sharp look of the Classic Side Part, regular trims every 3-4 weeks are crucial. Ensure your barber is familiar with the style you wish to maintain and can tailor the cut to suit your face shape and hair type. Between barber visits, maintain the part daily and restyle as needed.

The Classic Side Part stands as a cornerstone of old-money hairstyles, providing a timeless and adaptable look that suits a broad spectrum of face shapes and personal styles.

2. The Slick Back Hairstyle for Men

Slick Back Old Money Hairstyle

Alt text: Men’s slick back hairstyle, an old money classic, showcasing sleekness and refined sophistication.

The Slick Back hairstyle is a timeless and sophisticated choice that exudes tasteful refinement. It’s achieved by meticulously brushing the hair back and away from the face, creating a distinctly sleek appearance.

The Slick Back: An Icon of Old Money Refinement

The Slick Back hairstyle gained significant popularity in the 1920s and 1930s, during the illustrious Golden Age of Hollywood. Celebrated stars like Clark Gable and Humphrey Bogart popularized this look, which soon became synonymous with the image of the suave gentleman.

Clark Gable and Humphrey Bogart Slick Back Old Money Hairstyle

Alt text: Old money hairstyle inspiration from Clark Gable and Humphrey Bogart, both known for their slick back looks.

Left to right: Clark Gable and Humphrey Bogart’s slick back hairstyles. The Slick Back’s association with the old-money aesthetic is rooted in its ability to project confidence, refinement, and an air of effortless style.

Ideal Hair Texture, Length, and Volume for the Slick Back

The Slick Back is most effective with medium to thick hair types that have a slight natural wave or are straight. The hair should be long enough to be combed back and maintain the style, typically requiring about 3-5 inches on top and 1-2 inches on the sides and back. Aim for a balanced volume that results in a smooth, sleek appearance without looking flat or devoid of life.

Celebrities Who Master the Slick Back Hairstyle

• Leonardo DiCaprio: His Slick Back in “The Great Gatsby” perfectly captured the old-money charm and sophistication of the style.

Leonardo DiCaprio Slick Back Old Money Hairstyle

Alt text: Leonardo DiCaprio’s slick back hairstyle in The Great Gatsby, embodying old money elegance and charm.

Leonardo DiCaprio’s slick back hairstyle.

• Michael Douglas: Known for his consistently sharp and sophisticated slick back.

Michael Douglas Slick Back Old Money Hairstyle

Alt text: Michael Douglas’s classic slick back hairstyle, a timeless example of old money grooming.

Michael Douglas’ slick back hairstyle.

• Jake Gyllenhaal: Gyllenhaal often sports a contemporary slick back, showcasing its modern adaptability.

Jake Gyllenhaal Slick Back Old Money Hairstyle

Alt text: Jake Gyllenhaal’s modern slick back hairstyle, a contemporary take on old money style.

Jake Gyllenhaal’s slick back hairstyle.

Styling Techniques for the Perfect Slick Back

• Begin with damp, towel-dried hair. Apply a small amount of pomade or hair gel, ensuring it is distributed from the roots through to the ends.
• Use a wide-toothed comb to slick the hair back, starting at the forehead and moving towards the crown.
• For a high-gloss finish, refine the look with a fine-toothed comb to achieve a smooth, even surface.
• Blow-dry the hair backwards, using a concentrator nozzle to enhance the sleekness. Finish with additional pomade or hair spray for increased hold and shine.

Facial Hairstyle Pairings

The Slick Back hairstyle is best complemented by a clean-shaven face, which accentuates its sophisticated appearance. However, a well-maintained beard or mustache can introduce a touch of masculinity and create a more contemporary, edgy look.

Recommended Hair Products for the Slick Back

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

Maintenance and Barber Visits

Regular trims every 4-6 weeks are advised to maintain the Slick Back’s polished appearance. Ensure your barber understands the style you aim to uphold and can tailor the cut to fit your hair type and face shape. Between salon visits, restyle the Slick Back daily using appropriate products and techniques.

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

3. The Ivy League Scholarly Chic Hairstyle for Men

Ivy League Old Money Hairstyle

Alt text: Men’s Ivy League hairstyle, an old money scholarly chic look, showcasing neatness and preppy elegance.

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 with a slight quiff at the front, sharply tapered sides, and a crisp side part.

Ivy League Scholarly Chic: The Epitome of Old Money Style

Named after the prestigious Ivy League universities in the United States—Harvard, Yale, and Princeton—the Ivy League style emerged in the 1920s. It gained traction among the young, affluent men attending these esteemed institutions.

Ivy League Prep University Life 1930s 1940s

Alt text: Vintage image of Ivy League prep university life from the 1930s-1940s, reflecting the old money aesthetic and scholarly chic.

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

Ideal Hair Texture, Length, and Volume for the Ivy League Cut

Fine to medium hair with a slight natural wave is best suited for a flawless Ivy League haircut. This texture facilitates a neat, structured appearance while maintaining a hint 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 about 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 enhances the hairstyle’s crisp lines and refined silhouette, characteristic of classic men’s haircut styles.

Celebrities Embodying the Ivy League Scholarly Chic Hairstyle

• John F. Kennedy: A quintessential figure of Ivy League style, JFK’s haircut was a defining aspect of his polished image.

John F. Kennedy Ivy League Hairstyle

Alt text: John F. Kennedy’s iconic Ivy League style haircut, a symbol of old money and scholarly chic.

John F. Kennedy’s Ivy League style haircut.

• Ryan Gosling: Often seen sporting a modern take on the Ivy League haircut, Gosling showcases the style’s versatility and lasting appeal.

Ryan Gosling Ivy League Hairstyle

Alt text: Ryan Gosling’s contemporary Ivy League style haircut, demonstrating its modern appeal and scholarly chic.

Ryan Gosling’s Ivy League style haircut.

Styling Techniques for the Ivy League Hairstyle

• On slightly damp hair, apply a small amount of pomade or styling cream. Focus on the roots and work the product through to the ends with your fingers.
• Use a fine-toothed comb to create a sharp side part, starting from the crown and moving towards the temple.
• With a blow dryer set to medium heat and speed, dry the hair on top. Use a small round brush to create volume and a subtle quiff at the front.
• Once the top hair is dry and styled, gently refine the quiff with your fingers or a comb to ensure a neat, structured finish.

Facial Hairstyle Pairings

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, for gentlemen seeking to add a touch of vintage charm and sophistication, a well-groomed mustache is an excellent option. A neatly trimmed, classic mustache style, such as the chevron or pyramidal, can enhance the Ivy League’s old-money aesthetic and provide a subtle nod to the style icons of past eras.

Recommended Hair Products for the Ivy League Cut

Consider Baxter of California Clay Pomade, a water-based pomade that offers medium hold and a matte finish, perfect for achieving the Ivy League’s structured yet natural look. American Crew’s Forming Cream, with its light to medium hold and low-shine finish, is also ideal for maintaining the Ivy League’s polished yet understated appearance. To secure your Ivy League haircut and protect against humidity and frizz, a lightweight hair spray like Oribe’s Superfine Hair Spray is essential.

Maintenance and Barber Visits

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

The Ivy League haircut is a timeless old-money style that projects an air of intelligence, refinement, and understated elegance.

4. The Taper Fade Hairstyle for Men

Taper Fade Old Money Hairstyle

Alt text: Men’s taper fade hairstyle, an old money influenced modern cut, blending classic elegance with clean lines.

The taper fade is a contemporary hairstyle that masterfully blends the classic elegance of old-money aesthetics with the fresh, clean cuts favored by today’s discerning gentlemen. This haircut is characterized by a gradual taper, starting with longer lengths on top and progressively shortening down the sides and back, creating a smooth, blended transition.

The Taper Fade: A Modern Take on Old Money Elegance

While the taper fade has surged in popularity recently, its origins can be traced back to the classic, clean-cut hairstyles traditionally favored by the wealthy and influential throughout the 20th century. Gaining momentum in the 1940s, the taper fade’s emphasis on neatness, structure, and precision reflects the enduring values of the old-money aesthetic.

Taper Fade Hairstyle History

Alt text: Historical context of the taper fade hairstyle, showing its evolution and connection to old money grooming standards.

At the same time, its modern interpretations offer increased flexibility and personal expression. The taper fade represents a refined mix of traditional and contemporary styling, making it a top choice for gentlemen aiming to project elegance in both professional and social settings.

Ideal Hair Texture, Length, and Volume for the Taper Fade

The taper fade is remarkably versatile, adaptable to a wide range of hair types, textures, and lengths. However, to achieve 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 section of hair depends on your personal styling preferences, but a range of 1-4 inches is generally recommended. This length allows for diverse styling options, from sleek and smooth to textured and tousled, while maintaining the taper fade’s signature blended appearance. In terms of volume, the aim is to achieve a balanced, proportional look that complements your facial features and head shape.

Celebrities Sporting the Taper Fade Hairstyle

• Justin Timberlake: Timberlake’s polished looks often feature the taper fade, demonstrating its versatility and suitability for various personal styles and occasions—from red-carpet events to casual settings.

Justin Timberlake Taper Fade Old Money Hairstyle

Alt text: Justin Timberlake’s sleek taper fade haircut, exemplifying old money style in a modern context.

Justin Timberlake’s taper fade haircut.

• Ryan Reynolds: Reynolds’ clean-cut yet slightly textured taper fade exemplifies how the style can be tailored to suit various personal styles and events, from formal red carpets to everyday casual scenarios.

Ryan Reynolds Taper Fade Old Money Hairstyle

Alt text: Ryan Reynolds’ clean-cut taper fade haircut, a versatile and modern old money hairstyle.

Ryan Reynolds’ taper fade haircut.

• 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 confidence and adaptability.

Michael B. Jordan Taper Fade Old Money Hairstyle

Alt text: Michael B. Jordan’s sharp taper fade haircut, a contemporary and confident take on old money grooming.

Michael B. Jordan’s taper fade haircut.

Styling Techniques for the Taper Fade

• Begin 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 using your fingers or a comb.
• Use a blow dryer set to medium heat and speed to dry the hair on top. Simultaneously, use 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 a soft-bristled brush to gently blend the longer hair on top with the tapered sides and back.
• To finish and ensure a lasting hold, apply a small amount of hair spray or a light-hold styling product, like grooming cream or texture spray, to the hair on top.

Facial Hairstyle Pairings

The taper fade’s versatility extends to its compatibility with various facial hairstyles, allowing gentlemen to customize their look to 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, a carefully trimmed beard, or a precisely styled goatee can enhance the taper fade’s old-money aesthetic while allowing for greater 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. Recommended options include:

Hanz de Fuko Claymation, a matte-finish styling product that combines clay’s strength with wax’s flexibility, ideal for creating textured yet controlled taper fade styles. For those preferring a sleeker, more polished taper fade, Uppercut Deluxe Pomade offers the perfect combination of medium hold and high shine. Baxter of California’s Clay Effect Style Spray is excellent when a lightweight, texturizing finish is desired.

Maintenance and Barber Visits

Depending on your hair’s natural growth rate and desired level of precision, scheduling barber appointments every 2-4 weeks is recommended.

5. The Undercut Hairstyle for Men

Undercut Old Money Hairstyle

Alt text: Men’s undercut hairstyle, an old money inspired modern bold look, contrasting short sides with longer top.

The undercut is a striking, modern hairstyle that merges the refined appeal of old-money aesthetics with a contemporary, daring twist. This attention-grabbing look features short, buzzed sides and back, sharply contrasting with 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, and appealing to those who embrace individuality.

The Undercut: Rebellious Refinement in Old Money Style

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

Undercut History

Alt text: Historical context of the undercut hairstyle, showing its evolution and modern relevance to old money style.

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.

Ideal Hair Texture, Length, and Volume 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. The ideal length for the top portion is 2-5 inches, allowing for various styling options and dramatic volume. The sides and back are usually clipped very short, using a #1 or #2 guard, or even fully buzzed. This sharp distinction between the top and sides creates a bold, eye-catching silhouette.

Celebrities Rocking the Undercut Hairstyle

• Brad Pitt: Pitt has sported various undercut styles, highlighting the hairstyle’s rugged, masculine appeal.

Brad Pitt Undercut Old Money Haircut

Alt text: Brad Pitt’s undercut haircut, showcasing its rugged and masculine appeal within an old money context.

Brad Pitt’s undercut haircut.

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

Adam Levine Undercut Old Money Haircut

Alt text: Adam Levine’s edgy undercut haircut, blending rock-and-roll style with old money influences.

Adam Levine’s undercut haircut.

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

Cillian Murphy Undercut Old Money Haircut

Alt text: Cillian Murphy’s vintage-inspired undercut haircut in Peaky Blinders, a sharp and sophisticated old money look.

Cillian Murphy’s undercut haircut.

Styling Techniques for the Undercut

• Start with clean, dry hair and apply a small amount of high-hold pomade or styling clay to the longer hair on top.
• Style the top hair 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 for extra volume and lift.
• Apply a small amount of hairspray or texturizing spray to hold the style in place and add definition.

Facial Hairstyle Pairings

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, while a clean-shaven face highlights the undercut’s sharp lines and bold contrast. Consider pairing your undercut with neatly trimmed stubble or a short, well-defined beard for a balanced, rugged yet refined look.

Recommended Hair Products for the Undercut

Layrite Cement Clay provides a firm, pliable hold with a natural, matte finish. For a classic, slick look with high shine, Suavecito’s oil-based pomade offers superior hold and long-lasting control. Kevin Murphy Rough Rider clay provides a stronghold and a matte finish for various textures and styles.

Maintenance and Barber Visits

Maintain the undercut’s sharp appearance with regular barber visits every 2-3 weeks. Between appointments, use quality hair products and restyle as needed.

6. The Classic Pompadour Hairstyle for Men

Classic Pompadour Old Money Hairstyle Men

Alt text: Men’s classic pompadour hairstyle, an old money vintage look, showcasing volume and old-school 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, creating impressive volume that commands attention. The pompadour is a daring choice for men who appreciate the refined, dapper aesthetics of a bygone era, ideal for recalling the elegance and panache of classic Hollywood icons.

The Pompadour: A Legacy of Old Money Sophistication

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. The style gained popularity in the 1950s and 1960s, worn by influential musicians and celebrities like Elvis Presley and Johnny Cash.

Elvis Presley and Johnny Cash Classic Pompadour Haircut

Alt text: Old money hairstyle inspiration from Elvis Presley and Johnny Cash, both icons of the classic pompadour haircut.

Left to right: Elvis Presley and Johnny Cash’s classic pompadour hairstyles. 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 with old-money sensibilities.

Ideal Hair Texture, Length, and Volume for the Pompadour

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

Celebrities Known for the Pompadour Hairstyle

• Elvis Presley: Presley’s legendary pompadour became a defining feature of his iconic style, inspiring generations of fans to emulate his look.

Elvis Presley Classic Pompadour Old Money Hairstyle

Alt text: Elvis Presley’s legendary classic pompadour haircut, an iconic old money hairstyle.

Elvis Presley’s classic pompadour haircut.

• James Dean: Dean’s effortlessly cool take on the pompadour helped cement the style’s association with rebellious, bad-boy charm.

James Dean Classic Pompadour Old Money Hairstyle

Alt text: James Dean’s effortlessly cool classic pompadour haircut, embodying rebellious old money charm.

James Dean’s classic pompadour haircut.

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

David Beckham Pompadour Old Money Hairstyle

Alt text: David Beckham’s modern pompadour hairstyle, a versatile and contemporary take on old money style.

David Beckham’s pompadour hairstyle.

Styling Techniques for the Classic Pompadour

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

Facial Hairstyle Pairings

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

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 in place all day. Baxter of California’s Hard Cream Pomade is an excellent choice for a more natural, pliable hold with a subtle sheen. Suavecito Firme Hold Pomade offers a strong, long-lasting hold with a high-shine finish, perfect for a traditional, slick pompadour.

Maintenance and Barber Visits

Regular barber visits every 3-4 weeks are crucial to maintaining the pompadour’s precise shape and neatly trimming the sides and back. Daily styling with the appropriate products is necessary to ensure the pomp retains its volume and structure.

7. The Quiff Hairstyle for Men

Quiff Old Money Haircut

Alt text: Men’s quiff hairstyle, an old money inspired modern look, combining pompadour elements with a textured finish.

The quiff is a modern hairstyle that combines elements of the classic pompadour and the 1950s-inspired slick back. This cut features longer hair on top, styled up and back to create volume and height, while the sides and back are kept shorter for a clean, contemporary look. The quiff balances the structured elegance of old-money hairstyles with the relaxed, textured appeal of modern styling.

The Quiff: A Modern Interpretation of Old Money Style

While the quiff is a relatively modern hairstyle, it draws inspiration from the classic pompadour, which has deep roots in old-money fashion. 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.

James Dean 50s Quiff Haircut

Alt text: James Dean’s 50s quiff haircut, a vintage inspiration for the modern quiff and old money style.

The quiff’s adaptability allows it to be styled more relaxed and tousled, 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.

Ideal Hair Texture, Length, and Volume for the Quiff

The quiff works best with medium to thick hair with a slight natural wave or straight texture. The ideal length for the top portion is 2-4 inches, allowing for enough volume and height to create the signature quiff shape. The sides and back should be shorter, usually between 0.5 and 2 inches, depending on the desired contrast level and personal preference. The quiff’s volume can be customized to suit individual tastes, from a more understated, textured look to a bold, sky-high statement.

Celebrities Sporting the Quiff Hairstyle

• Zac Efron: Efron’s modern quiff features a textured, tousled top and shorter sides, showcasing the style’s youthful, effortless appeal.

Zac Efron quiff old money hairstyle

Alt text: Zac Efron’s textured quiff hairstyle, a youthful and effortless take on old money hair.

Zac Efron’s quiff hairstyle.

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

Chris Pine Quiff Old Money Hairstyle

Alt text: Chris Pine’s sleek and voluminous quiff hairstyle, blending old-school sophistication with modern old money style.

Chris Pine’s quiff hairstyle.

• 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.

David Gandy Quiff Old Money Hairstyle

Alt text: David Gandy’s classic quiff hairstyle with a side part, showcasing versatility and timeless old money appeal.

David Gandy’s quiff hairstyle.

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.
• 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.
• 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.
• For a more relaxed, tousled look, use your fingers to gently break up the quiff and create a natural, textured finish.

Facial Hairstyle Pairings

The quiff’s modern, versatile nature allows it to be paired with various facial hair styles. A clean-shaven face can highlight the quiff’s polished, sophisticated appearance, while well-groomed stubble or a short beard can add a rugged, masculine edge. 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.

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. For a high-shine look, use a water-based pomade like Imperial Barber Classic Pomade.

Maintenance and Barber Visits

To keep your quiff looking its best, schedule regular barber visits every 4-6 weeks to maintain the proper length and shape. Between appointments, wash and condition your hair regularly and restyle it as needed using your preferred products.

8. The Crew Cut Hairstyle for Men

Military Crew Cut mens haircuts

Alt text: Men’s crew cut hairstyle, an old money inspired military look, showcasing neatness and low maintenance.

The crew cut is a classic, low-maintenance hairstyle featuring short hair all around the head and slightly longer hair on top that gradually tapers down to the sides and back. 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.

The Crew Cut: Practicality and Prestige in Old Money Style

The crew cut originated in the 1920s and 1930s as a popular haircut among university crew teams, hence its name. During World War II, the hairstyle gained widespread popularity as a practical and low-maintenance cut for military personnel.

Crew Cut Men History

Alt text: Historical image of men with crew cut hairstyles in the 1920s and 1930s, illustrating its old money origins and practical elegance.

Men’s crew cut hair in the 1920s and 1930s. 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. The style’s simplicity and practicality align with the understated elegance and academic discipline associated with old-money families.

Ideal Hair Texture, Length, and Volume for the Crew Cut

The crew cut works well with most hair types and textures, from fine to thick and straight to wavy. 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. The crew cut’s volume is minimal, as the short length keeps the hair close to the scalp. This low-volume, no-fuss style is perfect for men who prefer a neat, tidy appearance without requiring extensive styling.

Celebrities Sporting the Crew Cut Haircut

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

Ryan Reynolds Crew Cut

Alt text: Ryan Reynolds’ classic crew cut hairstyle, a timeless and versatile old money look.

Ryan Reynolds’s crew cut.

• Tom Hardy: Hardy’s crew cut with slightly longer hair on top adds a modern, textured twist to the traditional style.

Tom Hardy Crew Cut

Alt text: Tom Hardy’s textured crew cut hairstyle, a modern and rugged take on the old money classic.

Tom Hardy’s crew cut.

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

Channing Tatum Crew Cut

Alt text: Channing Tatum’s versatile crew cut hairstyle, effortlessly transitioning between casual and formal old money styles.

Channing Tatum’s crew cut.

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.
• 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.
• For a more polished appearance, brush or comb to smooth the hair on top and create a neat, uniform finish.
• If desired, apply a small amount of hair wax or clay to the hair on top for added texture and definition.

Facial Hairstyle Pairings

The crew cut’s clean, masculine appearance pairs well with various facial hairstyles. A clean-shaven face can highlight the crew cut’s neat, polished look, while well-groomed stubble or a short beard can add a rugged, masculine touch. 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.

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. For a matte, textured finish, try Baxter of California Clay Pomade, which offers a strong, pliable hold without added shine.

Maintenance and Barber Visits

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. Between appointments, wash your hair regularly and style as needed with minimal product.

The crew cut is a timeless, low-maintenance hairstyle that embodies the clean, masculine aesthetics of old-money grooming. 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.

9. The Buzz Cut for Men

Classic Buzz Cut hairstyles

Alt text: Men’s buzz cut hairstyle, a minimalist old money look, exuding confidence and masculinity with low maintenance.

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, usually with electric clippers, resulting in a uniform length that typically 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.

The Buzz Cut: Minimalist Confidence in Old Money Style

While the buzz cut is not a traditional old-money hairstyle, its origins in the military and emphasis on simplicity and practicality align with old-money aesthetics. The buzz cut’s minimalist appearance and low-maintenance nature can be seen as a rejection of excess and a focus on functionality, often associated with old-money values. Additionally, the buzz cut’s popularity among influential figures, such as actors, athletes, and business people, has helped to elevate its status, making it a timeless, classic choice for men across various social and economic backgrounds.

Ideal Hair Texture, Length, and Volume for the Buzz Cut

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

Celebrities Sporting the Buzz Haircut

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

David Beckham Buzz Cut

Alt text: David Beckham’s buzz cut hairstyle, a versatile and confident old money look.

David Beckham’s buzz cut hairstyle.

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

Zayn Malik buzz cut

Alt text: Zayn Malik’s modern buzz cut hairstyle with faded sides, an edgy and contemporary old money style adaptation.

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

Styling Techniques for the Buzz Cut

• After showering, towel dry your hair or allow it to air dry.
• If desired, apply a small amount of matte pomade or wax to the hair to add a hint of texture and definition.
• For a more polished look, use a soft-bristled brush to smooth the hair and create a neat, uniform appearance.

Facial Hairstyle Pairings

The buzz cut’s minimalist, masculine appearance pairs well with various facial hairstyles. A clean-shaven face can highlight the cut’s sleek, streamlined look, while well-groomed stubble or a short beard can add a rugged, masculine edge. 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.

Recommended Hair Products for the Buzz Cut

Due to the buzz cut’s short length, minimal product is needed to maintain the style. However, the following products can help to keep your hair looking healthy and add a touch of texture or definition: 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. Baxter of California Grooming Cream offers a lightweight, nourishing formula that moisturizes the scalp and adds a subtle, matte finish to the hair.

Maintenance and Barber Visits

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. Between appointments, wash your hair regularly with a gentle shampoo to keep the scalp clean and healthy.

The buzz cut is a minimalist, confident hairstyle that embodies simplicity and practicality. Its fuss-free nature and masculine appearance make this cut ideal for men who value a no-nonsense approach to grooming while still maintaining a stylish look.

10. The Comb Over Hairstyle for Men

Comb Over Old Money Style Haircut

Alt text: Men’s comb over hairstyle, an old money style haircut, showcasing sophistication and modern elegance.

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

The Comb Over: Timeless Sophistication in Old Money Fashion

The comb-over has a rich history dating back to the early 20th century when it was a popular choice among wealthy and influential men. The style’s association with old-money fashion lies in its neat, polished appearance and ability to convey sophistication and refinement. Over the decades, the comb-over has evolved to incorporate modern elements, such as tapered sides and textured finishes, while maintaining its classic roots. 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.

Ideal Hair Texture, Length, and Volume for the Comb Over

The comb-over works best with medium to fine hair with a slight natural wave or straight texture. The ideal length for the hair on top is between 2-4 inches, allowing for enough length to create a smooth, swept-over look. The sides and back should be kept shorter, usually between 0.5-2 inches, depending on the desired contrast level and personal preference. The comb-over’s volume can be customized to suit your unique face shape, from a sleek, flat look to a more voluminous, textured style.

Celebrities Sporting the Comb Over Haircut

• George Clooney: Clooney’s classic comb-over with a side part exemplifies the style’s timeless appeal and its ability to project an image of refined sophistication.

George Clooney Classic comb-over Hairstyle

Alt text: George Clooney’s classic comb over hairstyle, a timeless example of old money sophistication and style.

George Clooney’s classic comb-over hairstyle.

• 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.
• Leonardo DiCaprio: DiCaprio’s comb-over with a subtle taper and side part demonstrates the style’s versatility and its ability to complement various face shapes and personal styles.

Leonardo DiCaprio Comb Over Hairstyle

Alt text: Leonardo DiCaprio’s versatile comb over hairstyle, showcasing its adaptability to various old money styles.

Leonardo DiCaprio’s comb-over hairstyle.

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.
• Using a blow dryer and a round brush, sweep the hair on top over to one side, creating volume and a smooth, polished finish.
• For a more textured, modern look, use a matte pomade or clay to add definition and movement to the hair on top.
• 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.

Facial Hairstyle Pairings

The comb-over’s sophisticated, polished appearance pairs well with various facial hairstyles. A clean-shaven face can highlight the comb over’s neat, refined look, while well-groomed stubble or a short beard can add a touch of masculinity and texture. 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.

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: Blind Barber 90 Proof Pomade provides a strong, pliable hold with a moderate shine, making it ideal for creating sleek, polished combovers. Hanz de Fuko Claymation offers a matte, textured finish with a stronghold, perfect for more modern, volumized comb-over styles.

Maintenance and Barber Visits

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. The comb-over haircut is ideal for men who want to project confidence while wearing modern old-money aesthetics infused with modern trends.

11. The French Crop Hairstyle for Men

French Crop Fringe haircuts for men

Alt text: Men’s French crop hairstyle, an old money inspired simple yet stylish look, combining classic and modern elements.

The French crop, also known as the crop top or textured crop, is a simple yet stylish hairstyle that combines elements of the classic Caesar cut with modern textures and finishes. This versatile look features short hair on the back and sides, with a slightly longer, textured top styled forward or to the side. 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.

The French Crop: Classic Simplicity in Old Money Style

While the French crop may not have a direct association with old-money fashion, its roots in the classic Caesar cut and emphasis on simplicity align with old-money values. The Caesar cut originated in ancient Rome and was popularized by the Roman emperor Julius Caesar. It has since become a timeless, iconic hairstyle. The French crop’s modern interpretation of this classic look, with its textured top and clean, tapered sides, reflects a balance between traditional style and contemporary preferences. This fusion of old and new makes the French crop appealing to men who appreciate the elegance and refinement of old-money aesthetics.

Ideal Hair Texture, Length, and Volume for the French Crop

The French crop works well with most hair types and textures, from fine to thick and straight to wavy. The ideal length for the top is 1-2 inches, which allows enough hair to create a textured, slightly messy appearance. 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. The French crop’s volume is typically moderate, focusing on texture rather than height.

Celebrities Sporting the French Crop Haircut

• 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.

Cillian Murphy French Crop haircut

Alt text: Cillian Murphy’s French crop haircut in Peaky Blinders, a versatile old money style for period and modern looks.

Cillian Murphy’s French crop haircut.

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

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.
• 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.
• 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.
• For a more polished appearance, use a comb to style the hair on top forward or to the side, creating a neat, uniform finish.

Facial Hairstyle Pairings

The French crop’s simple, versatile nature allows it to pair well with various facial hairstyles. A clean-shaven face can highlight the crop’s neat, refined appearance, while well-groomed stubble or a short beard can add a touch of ruggedness and masculinity. 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.

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: Baxter of California Clay Pomade offers a pliable hold with a matte finish, ideal for creating textured, tousled French crop styles. 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.

Maintenance and Barber Visits

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.

12. The Side Fringe Hairstyle for Men

Side Fringe haircuts for men

Alt text: Men’s side fringe hairstyle, a youthful old money look, combining classic side-swept with modern textured finish.

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

The Side Fringe: A Modern Update on Classic Old Money Style

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. The side-swept style has been a staple of men’s grooming since the 1940s and has been adapted to incorporate modern elements and trends. The side fringe’s contemporary interpretation of this timeless look, with its tousled texture and softer, more natural appearance, reflects a shift in men’s grooming preferences towards styles prioritizing ease, individuality, and self-expression. While not strictly adhering to old-money aesthetics, the side fringe represents a continuation of the classic side-swept tradition, updated for the modern age.

Ideal Hair Texture, Length, and Volume for the Side Fringe

The side fringe works best with medium to thick hair with a slight natural wave or straight texture. 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. 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. 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.

Celebrities Sporting the Side Fringe Hairstyles

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

Timothée Chalamet Side Fringe Hairstyle

Alt text: Timothée Chalamet’s side fringe hairstyle, a modern and effortlessly cool take on old money youthfulness.

Timothée Chalamet’s side fringe hairstyle.

• Harry Styles: Styles’ iconic side fringe features a longer, tousled top and textured sides, epitomizing the style’s youthful, carefree charm.
• 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.

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.
• 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.
• 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, piecey appearance.
• For a more relaxed, tousled look, use your fingers to gently mess up the fringe and add a carefree, lived-in vibe.

Facial Hairstyle Pairings

The side fringe’s youthful, laid-back appearance pairs well with various facial hairstyles, particularly those emphasizing a fresh look. A clean-shaven face can highlight the side fringe’s soft, textured appearance and keep the focus on the hair. For a more balanced, contemporary look, consider pairing your side fringe with 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.

Recommended Hair Products for the Side Fringe

To achieve and maintain the perfect side fringe, invest in products that enhance volume, texture, and movement: Bumble and Bumble Surf Spray is 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. Hanz de Fuko Scheme Cream is a lightweight, versatile styling cream that provides a soft, pliable hold with a natural finish, perfect for creating a smooth, defined fringe.

Maintenance and Barber Visits

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. The side fringe is a youthful, textured hairstyle that combines elements of the classic side-swept look with modern, tousled finishes. Its laid-back, casual vibe and ability to soften facial features make it an appealing choice for younger men who want to embrace a more relaxed, contemporary aesthetic while still nodding to the timeless tradition of the side-swept style.

13. The Regulation Cut Hairstyle for Men

Regulation Cut Men

Alt text: Men’s regulation cut hairstyle, an old money inspired military look, showcasing discipline and neatness.

The regulation cut, also known as the high and tight or the military cut, is a clean, precise hairstyle that adheres to the strict grooming standards of the armed forces. 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. The regulation cut’s sharp, disciplined appearance and its association with military tradition make it popular among men who value order, efficiency, and a neat, put-together look.

The Regulation Cut: Discipline and Order in Old Money Style

While the regulation cut may not be directly associated with old-money fashion, its roots in military tradition and emphasis on discipline, order, and cleanliness align with certain old-money values. The military has long been associated with the upper echelons of society, with many wealthy and influential families sending their sons to serve in the armed forces as a rite of passage and a mark of social status.

Regulation Cut Military History

Alt text: Historical context of the regulation cut hairstyle, showing its military origins and connection to old money values of discipline and order.

The regulation cut’s adherence to strict grooming standards and projection of a neat, put-together appearance reflects the importance placed on self-discipline and presentability within old-money circles. By embracing the regulation cut, men can tap into this tradition of military precision and the associated values of order, efficiency, and respectability.

Ideal Hair Texture, Length, and Volume for the Regulation Cut

The regulation cut works well with most hair types and textures, as the short length and high-and-tight style minimize the impact of individual hair characteristics. 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. Due to the extremely short length, the regulation cut has minimal volume and is characterized by a flat, close-to-the-head appearance. The lack of volume contributes to the style’s neat, disciplined look and low-maintenance nature.

Celebrities Sporting the Regulation Cut

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

Jake Gyllenhaal Regulation Cut

Alt text: Jake Gyllenhaal’s regulation cut hairstyle in Jarhead, showcasing its military origin and tough, masculine old money style.

• Tom Hardy: Hardy’s haircut in the film “Warrior” demonstrates the style’s versatility and potential to complement a muscular, athletic physique.
• Justin Timberlake: Timberlake’s regulation cut during his early solo career highlighted the style’s clean, sharp appearance and ability to convey a sense of discipline and focus.

Styling Techniques for the Regulation Cut

• Due to the regulation cut’s extremely short length, styling is minimal and primarily focused on maintaining the hair’s neat, uniform appearance.
• 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.

Facial Hairstyle Pairings

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

Recommended Hair Products for the Regulation Cut

Given the regulation cut’s extremely short length and low-maintenance nature, minimal product is needed to maintain the style. However, the following products can help 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. 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.

Maintenance and Barber Visits

Frequent barber visits are essential to maintaining the precise, uniform appearance of the regulation cut. Schedule appointments every 1-2 weeks to keep the sides and back closely cropped and the top trimmed to the desired length. 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.

The regulation cut is a clean, precise hairstyle embodying the discipline, order, and efficiency of military tradition. Its sharp, put-together appearance and low-maintenance nature make it an appealing choice for men who value neatness, practicality, and adherence to grooming standards.

14. The Short Curtain Hairstyle for Men

Short Curtain

Alt text: Men’s short curtain hairstyle, a retro old money look, showcasing vintage charm and effortless cool.

The short curtain hairstyle is a retro-inspired look that has recently returned to men’s fashion. This stylish, low-maintenance cut features short hair on the sides and back, with slightly longer hair on top that is parted in the middle and allowed to fall naturally to either side, resembling a curtain. The short curtain’s vintage charm and ability to blend classic and contemporary elements make it a popular choice among fashion-forward men who appreciate a touch of nostalgia in their style.

The Short Curtain: Retro Nostalgia in Old Money Style

The short curtain hairstyle originated in the 1990s and reached peak popularity thanks to celebrities like Leonardo DiCaprio and Johnny Depp.

Leonardo DiCaprio and Johnny Depp Short Curtain Hair 90s

Alt text: 90s old money hairstyle inspiration from Leonardo DiCaprio and Johnny Depp, both icons of the short curtain haircut.

from left to right: Johnny Depp and Leonardo DiCaprio’s short curtain haircut in the 90s. The look is not directly associated with old-money fashion. Still, the short curtain’s revival in recent years reflects a broader nostalgia trend and a renewed appreciation for vintage hairstyles. The short curtain’s blend of classic and contemporary features, low-maintenance nature, and effortless cool factor align with the old-money aesthetic’s emphasis on timeless style, understated elegance, and a certain nonchalance.

Ideal Hair Texture, Length, and Volume for the Short Curtain

The short curtain hairstyle works best with straight to slightly wavy hair with a medium to fine texture. 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 to either side. The sides and back are usually kept shorter, between 1 and 2 inches, to create a slight contrast and emphasize the curtain effect on top. The short curtain’s volume is typically moderate, focusing on maintaining a natural, effortless appearance rather than creating excessive height or fullness.

Celebrities Sporting the Short Curtain Haircut

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

Charles Melton Short Curtain Hairstyle

Alt text: Charles Melton’s tousled short curtain hairstyle, a versatile and customizable old money retro look.

Charles Melton’s short curtain haircut.

• Patrick Schwarzenegger: Schwarzenegger’s short curtain with a side part and a polished finish highlights the style’s ability to appear laid-back and put-together, depending on the styling techniques used.

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.
• Using a comb, create a middle part, ensuring that the hair falls naturally to either side of the part.
• Allow the hair to air dry for a natural, effortless look, or use a blow dryer in a low heat setting to encourage the hair to fall in the desired direction.
• For a more polished appearance, use a small amount of pomade or wax to define the part and add shine, without disrupting the hair’s natural fall.

Facial Hairstyle Pairings

The short curtain hairstyle’s laid-back, youthful appearance pairs well with clean-shaven faces, which helps to maintain the focus on the hair and its unique parted style. However, for those who prefer facial hair, light stubble or a short, well-groomed beard can work with the short curtain, adding a touch of maturity and masculinity to the overall look. The key is to keep the facial hair neat and trimmed to avoid overwhelming the hairstyle’s effortless, natural vibe.

Recommended Hair Products for the Short Curtain

To achieve and maintain the perfect short curtain hairstyle, consider using the following products: Malin + Goetz Sage Styling Cream is a lightweight, moisturizing cream that provides a soft, natural hold and enhances the hair’s texture and shine. Aesop Violet Leaf Hair Balm is a nourishing, non-greasy balm that helps to tame frizz, add definition, and protect the hair from environmental stressors.

Maintenance and Barber Visits

To keep your short curtain hairstyle 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. Between appointments, wash your hair with a gentle, sulfate-free shampoo and conditioner to maintain the hair’s natural moisture and prevent damage. Style as needed using lightweight, non-greasy products that enhance the hair’s natural texture and fall.

The short curtain hairstyle is a retro-inspired look combining vintage charm, a contemporary cool factor, and a fresh appeal to fashion-forward men who appreciate a touch of nostalgia in their style while still embracing current trends.

15. The Edgar Haircut for Men

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

Alt text: Men’s Edgar haircut, a modern edgy old money style, showcasing sharp angular fringe and contemporary fashion.

The Edgar haircut, also known as the “South of France” haircut, is a modern, edgy style recently gaining popularity among young men. This haircut is characterized by its short, often faded sides and back, and a longer, textured top typically styled forward or upward to create a sharp, angular fringe. The Edgar’s distinctive silhouette and its association with contemporary fashion trends make it a popular choice among younger men who want to make a stylish statement and stand out.

The Edgar: Edgy Modernity in Old Money Context

While the Edgar haircut does not directly relate to old-money fashion or historical contexts, its modern, edgy appearance represents a departure from traditional, conservative hairstyles often associated with old-money aesthetics. However, the Edgar’s emphasis on precision cutting, clean lines, and bold styling can be seen as a contemporary interpretation of the attention to detail and grooming standards valued in old money circles. Edgar-style haircuts allow men to demonstrate self-expression and a willingness to take risks, qualities always admired in fashion-forward individuals, regardless of background.

Ideal Hair Texture, Length, and Volume for the Edgar Haircut

The Edgar haircut works best with straight to slightly wavy hair with a medium to thick texture. 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. The sides and back are usually faded or undercut, with the length gradually decreasing from the top to the bottom for a sharp, contemporary contrast. The Edgar’s volume is typically high, focusing on creating a bold, attention-grabbing silhouette that emphasizes the angular lines and textured finish of the hair on top.

Celebrities Sporting the Edgar Haircut

• Kylian Mbappé: Mbappé, the French professional footballer, has sported a sleek, well-defined Edgar haircut, showcasing the style’s sporty, youthful appeal and its potential for precision styling.

Kylian Mbappé Edgar Hairstyle

Alt text: Kylian Mbappé’s Edgar hairstyle, a sporty and youthful old money style with precision styling.

Kylian Mbappé’s Edgar hairstyle.

• Anwar Hadid: Hadid, the model and younger brother of Gigi and Bella Hadid, has been seen with a tousled, textured Edgar cut that demonstrates the style’s edgy, fashion-forward vibe.

Anwar Hadid Edgar Hairstyle

Alt text: Anwar Hadid’s textured Edgar hairstyle, showcasing its edgy and fashion-forward old money appeal.

Anwar Hadid’s Edgar hairstyle.

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

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.
• Using a comb or your fingers, style the hair on top forward or upward, creating a sharp, angular fringe that falls just above the eyebrows.
• Use a blow dryer on high heat to lock the style in place, directing the airflow upward and forward to emphasize the angular shape and texture of the fringe.
• For a more voluminous, textured look, use a small amount of matte clay or putty to define individual strands and create a slightly messy, edgy finish.

Facial Hairstyle Pairings

The Edgar haircut’s bold, contemporary appearance is often paired with clean-shaven faces, which helps to maintain the focus on the hair’s sharp lines and angular styling. However, for those who prefer facial hair, a well-groomed, shaped beard or goatee can work with the Edgar cut, adding an extra layer of dimension and personal style to the overall look. The key is to ensure that the facial hair is precisely trimmed and complements the clean, defined lines of the haircut.

Recommended Hair Products for the Edgar Haircut

To achieve and maintain the perfect Edgar haircut, consider using the following products: Hanz de Fuko Heavymade Pomade is a high-hold, water-based pomade with a strong, long-lasting hold and a natural, satin finish, ideal for creating sharp, angular styles. Layrite Cement Matte Hair Clay is a pliable, matte-finish clay with a strong, texturizing hold. It is perfect for achieving the Edgar’s signature disheveled, edgy look.

Maintenance and Barber Visits

Frequent barber visits are essential to maintain the Edgar haircut’s precise, angular appearance. Schedule appointments every 2-3 weeks to keep the sides and back faded or undercut and the top trimmed to the desired length and shape. Use lightweight, water-based styling products to restyle the hair as needed, ensuring that the angular fringe and textured finish remain intact.

What’s the Right Hairstyle for Me?

Choosing the perfect old-money hairstyle for you involves several key factors, such as your unique facial features, lifestyle, fashion style, and more. This section will explore these factors in detail and match hairstyles to various face shapes and age groups.

Old Money style grooming and hair

Alt text: Old money style grooming and hair, featuring a sophisticated gentleman with a classic hairstyle.

Face Shape: Finding Your Best Hairstyle Fit

Understanding your face shape is crucial when selecting a hairstyle that flatters your features and enhances your overall appearance. Take this simple and quick quiz to help you determine your face shape.

The main face shapes include:

Oval Face Shape

Characterized by a length slightly greater than its width, an oval face features a rounded jawline and a forehead that is just a bit wider than the chin. This versatile face shape pairs well with most hairstyles. Focus on styles that maintain the face’s natural balance and proportion.

Round Face Shape

A round face is almost equal in length and width, defined by a soft, curved jawline lacking prominent angles. For this shape, opt for hairstyles that add height and volume on top while keeping the sides and back short to elongate the face and introduce a more angular appearance.

Square Face Shape

The square face shape is defined by a strong, angular jawline and a forehead that is approximately the same width as the chin. Choose hairstyles that soften the strong angles of the jawline, such as styles with shorter sides and a slightly longer, textured top.

Heart Face Shape

A heart-shaped face is wider at the forehead and cheekbones, narrowing down to a pointed chin. Select hairstyles that balance the wider forehead and narrower chin, such as styles with side-swept fringes or a medium-length top with shorter sides.

Diamond Face Shape

The diamond face shape is widest at the cheekbones, with a narrower forehead, chin, and pointed jawline. Pick styles that add volume and width at the chin and forehead while keeping the hair closer to the head at the cheekbones to minimize width.

Hair Type and Texture: Tailoring Styles to Your Natural Hair

Your hair type and texture significantly influence which old-money hairstyles will work best for you. The main hair types include:

Straight Hair

Straight hair is naturally smooth and flat, lacking any discernible curl or wave. Most old-money hairstyles are achievable with straight hair, making it easier to achieve a sleek, polished appearance. Focus on styles that add volume and texture to prevent the hair from looking flat or lifeless.

Wavy Hair

Wavy hair falls in loose, S-shaped curves, more defined than straight hair but less curly. Embrace your natural texture by choosing styles that enhance the waves, such as the classic side part or the short curtain. Use lightweight, moisturizing products to define and control the waves without weighing them down.

Curly Hair

Curly hair forms tight, defined ringlets or coils from the scalp to the ends. Opt for old-money hairstyles that complement your natural curl pattern, such as the French crop or the regulation cut. Use products that provide moisture, definition, and frizz control, and consider using a diffuser when drying your hair to maintain the integrity of the curls.

Kinky/Coily Hair

Kinky or coily hair is characterized by very tight, densely packed curls or coils that may have a zig-zag or Z-shaped pattern. Select hairstyles that celebrate your natural texture, such as the buzz cut or a short, tapered afro. Use moisturizing, nourishing products to keep the hair healthy and defined, and consider protective styling techniques to minimize damage and maintain the hair’s natural pattern.

Lifestyle and Maintenance: Choosing a Practical Style

When choosing an old-money hairstyle, consider your lifestyle and the level of maintenance you’re willing to commit to. Some styles require frequent trims, daily styling, and specific products, while others are more low-maintenance and easily managed with minimal effort. If you have a busy lifestyle or prefer a more low-key approach to grooming, opt for old-money hairstyles that are simple, versatile, and easy to maintain, such as:

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

These styles typically require less frequent barber visits and can be styled quickly with minimal product, making them ideal for those who value simplicity and efficiency.

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

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

These styles often require more frequent trims, daily styling with specific products, and more time and effort to achieve the desired look. However, they also allow for greater self-expression and can be adapted to suit various occasions and personal preferences.

Old-Money Hairstyles by Age Groups: Styling Across Generations

While old-money hairstyles are timeless and can be worn by men of all ages, it’s important to understand that certain hairstyles may be perceived as more suitable for specific age groups, requiring adjustments accordingly.

Younger Men (18-30)

Younger men have the most flexibility when experimenting with old-money hairstyles, often able to pull off bolder, more contemporary looks without seeming out of place. Some styles that work particularly well for this age group include:

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

These styles offer a balance of classic sophistication and modern edge, allowing younger men to express their individuality while still adhering to the timeless principles of the old-money aesthetic.

Middle-Aged Men (31-50)

For middle-aged men, the focus should be on selecting old-money hairstyles that convey maturity, refinement, and a sense of established success. Some styles that work well for this age group include:

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

These styles offer a polished, sophisticated appearance well-suited to professional and social settings, while still allowing for personal style and customization.

Older Men (51+)

For older men, the key is to choose old-money hairstyles that are age-appropriate, flattering, and easy to maintain. Some styles that work particularly well for this age group include:

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

These styles offer a timeless, distinguished appearance that embraces the natural changes in hair texture and density that often come with age, while still projecting an air of refinement and sophistication.

Final Thoughts: Embracing Timeless Elegance

The old money aesthetic, associated with the upper echelons of society, embodies a confident look rooted in traditional values and understated wealth. In a world of fast fashion trends and new money displays, the old-money aesthetic remains a stronghold of steadfast refinement, conveying excellence and self-assurance.

An old-money hairstyle is central to achieving this distinguished look, serving as the quickest and most affordable way to cultivate an image of timeless elegance, refined sophistication, and a rich heritage. The key to selecting the right old-money hairstyle is to consider your features, lifestyle, and personal preferences, and choose a style that makes you feel confident, comfortable, and authentically you. By investing time in understanding these factors and experimenting with different options, you can discover the perfect old-money hairstyle that complements your unique style and helps you project the timeless, sophisticated image associated with this enduring aesthetic.

Style Like a True Gentleman: Beyond the Haircut

Before we conclude, here’s one of the best-kept secrets in men’s styling—a secret known only to a select few expert image consultants who are willing to share. True professional styling begins with knowing your unique body shape and seasonal color palette—paramount factors for choosing perfectly fitting clothes in colors that complement your skin, eyes, and hair.

Only then can a stylist effectively engage in styling by occasion, location, season, and time of day, selecting garments, footwear, and accessories from stylistically relevant heritage fashion brands to project high confidence and success.

The best part? You can discover your body shape, seasonal color palette, and ideal fashion style in less than 5 minutes, for free, using these four simple steps:

1. Find Your Body Shape

Different garments flatter different silhouettes, so knowing your body shape is the first step in dressing like a confident man. To find your unique body shape, take our free body shape quiz for men. Once you know your body shape, proceed to the second free quiz to discover your unique color palette.

2. Find Your Unique Color Palette

Remember, the garments that compose your outfits come in various colors, and you must ensure each hue complements your natural coloring. To do this, you need to find your seasonal color palette. Take our free seasonal color quiz for men to determine yours.

3. Find Your Ideal Fashion Style

By now, you should know your body shape and unique color palette. The next step is to discover your ideal personal fashion style. The quickest and simplest way is to take our free fashion style quiz for men, which includes insights into your ideal style, outfit ideas, relevant fashion brands, and much more.

4. Professional Image Consultancy with The VOU

For those seeking to style like a professional—by occasion, location, season, and time of day—our expert image consultants and fashion stylists are available to help. Our styling services for men are among the most comprehensive and detailed on the market, supported by leading stylists who will guide you step-by-step in creating looks that communicate affluence, elegance, and success.

Remember, wearing luxury brands is not enough. To look stylish, confident, and successful, you must first understand your body shape, color palette, and ideal personal style, and then style according to occasion, location, season, and time of day. Contact us today to save time, money, and headaches—it’s time to dress like a confident, successful gentleman with exquisite fashion taste. Your first styling assessment is on us!

Ru Amiri

With years of expertise in high-end fashion collaborations and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

Laurenti Arnault

With over twenty years of front-row fashion and styling events, collaborations with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.