Men's Classic Side Part Old Money Hairstyle
Men's Classic Side Part Old Money Hairstyle

Old Money Haircut Men: Timeless Styles for Sophisticated Gentlemen

Key Points to Remember

  • Select a haircut that complements your face shape and hair type.
  • Consider your daily routine and how much time you want to spend on hair care.
  • Choose hairstyles that are appropriate for your age and enhance your overall appearance.

Want to discover more? Continue reading the complete guide below ↓

1. Classic Side Part Hairstyle for Men

Men's Classic Side Part Old Money HairstyleMen's Classic Side Part Old Money Hairstyle

The classic side part is a quintessential men’s hairstyle recognized by its sharp, distinct part that runs laterally across the scalp, typically from the crown to the temple. The hair on top is intentionally left slightly longer than the sides, which are often tapered or faded to create a crisp and polished finish.

The Old Money Appeal of the Classic Side Part

Emerging in the 1920s and 1930s, the classic side part gained traction among men, propelled by iconic figures from Hollywood’s golden era such as Cary Grant and Fred Astaire. This style marked a shift from the longer, slicked-back hairstyles of previous decades, quickly becoming a hallmark of refined masculinity.

Cary Grant and Fred Astaire with Classic Side Part Old Money HaircutsCary Grant and Fred Astaire with Classic Side Part Old Money Haircuts

From left to right: Timeless elegance embodied by Cary Grant and Fred Astaire with their signature classic side-part haircuts.

The classic side part, with its clean lines and structured form, inherently communicates order and discipline, core tenets of the old-money style. This hairstyle is not just about appearance; it’s about projecting an image of understated wealth and timeless sophistication.

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

This style is ideally suited for men with medium to fine hair that possesses a slight natural wave. The hair on the top should be of sufficient length to allow for combing and maintaining a distinct part, generally around 2 to 4 inches. The sides are kept shorter, typically between 0.5 and 1 inch. The objective is to achieve a balanced volume that supports the style’s structure without appearing overly rigid or bulky.

Celebrities Known 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 icon.
    Jon Hamm's Classic Side Part Hairstyle - Old Money InspirationJon Hamm's Classic Side Part Hairstyle – Old Money Inspiration
  • George Clooney: Clooney’s silver fox side part is a celebrated example of this timeless old money haircut.
    George Clooney's Silver Fox Classic Side Part - A Mature Old Money LookGeorge Clooney's Silver Fox Classic Side Part – A Mature Old Money Look
  • David Beckham: Beckham has showcased various versions of the classic side part, highlighting its lasting appeal across generations.
    David Beckham's Modern Classic Side Part - Enduring StyleDavid Beckham's Modern Classic Side Part – Enduring Style
  • Ryan Gosling: Gosling’s rendition features a slightly longer top with a more relaxed, textured finish, proving the style’s versatility.
    Ryan Gosling's Relaxed Classic Side Part - Versatile and StylishRyan Gosling's Relaxed Classic Side Part – Versatile and Stylish

Styling Guide 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 from the roots to the ends.
  • Create a sharp, defined part using a fine-toothed comb, starting from the crown and moving towards the temple.
  • Blow-dry the top hair towards the part, using a round brush to add volume and ensure smoothness.
  • For a more casual appearance, gently tousle the top hair with your fingers while maintaining the structure of the part.

Facial Hair Pairings

The classic side part best complements a clean-shaven face, enhancing its sharp and polished aesthetic. However, a well-maintained moustache or a neatly trimmed beard can also harmonize with the style, adding a touch of vintage charm or contemporary sophistication.

Recommended Products

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

Maintenance Tips

Regular trims every 3 to 4 weeks are crucial to maintain the sharp look of the classic side part. Ensure your barber understands the style you’re aiming for and can tailor it to your face shape and hair type. Between barber visits, maintain the part daily and restyle as needed. The classic side part remains a cornerstone of old-money hairstyles, offering a timeless and adaptable look suitable for various face shapes and personal styles.

2. Slick Back Hairstyle for Men

Men's Slick Back Old Money HairstyleMen's Slick Back Old Money Hairstyle

The slick back is an enduringly sophisticated hairstyle that exudes tasteful refinement. It’s achieved by brushing the hair back and away from the face, creating a smooth, sleek appearance that speaks volumes of understated elegance.

The Old Money Allure of the Slick Back

The slick back hairstyle surged in popularity during the 1920s and 1930s, a period known as the Golden Age of Hollywood. Celebrities like Clark Gable and Humphrey Bogart popularized this look, which soon became synonymous with the suave gentleman.

Clark Gable and Humphrey Bogart Sporting Slick Back Old Money HaircutsClark Gable and Humphrey Bogart Sporting Slick Back Old Money Haircuts

Left to right: Icons of style, Clark Gable and Humphrey Bogart, with their signature slick back hairstyles embodying old money charm.

The slick back’s association with the old-money aesthetic lies in its inherent ability to convey confidence, refinement, and an effortless sense of style. It’s a hairstyle that speaks of tradition and timelessness, key elements of old money elegance.

Hair Texture, Length, and Volume for the Slick Back

The slick back is best suited for medium to thick hair with a slight natural wave or straight texture. The hair should be long enough to be combed back and maintain the style, typically around 3 to 5 inches on top and 1 to 2 inches on the sides and back. The goal is to achieve a balanced volume that creates a smooth, sleek appearance without looking flat or lifeless.

Celebrities Known for Slick Back Hairstyles

  • Leonardo DiCaprio: His slick back in “The Great Gatsby” perfectly captured the old-money charm and sophistication of the era.
    Leonardo DiCaprio's Slick Back in The Great Gatsby - Old Money EleganceLeonardo DiCaprio's Slick Back in The Great Gatsby – Old Money Elegance
  • Michael Douglas: Douglas’s slick back hairstyle is a testament to the style’s enduring appeal across generations.
    Michael Douglas's Timeless Slick Back - Generational StyleMichael Douglas's Timeless Slick Back – Generational Style
  • Jake Gyllenhaal: Gyllenhaal’s slick back demonstrates the style’s versatility and modern adaptability.
    Jake Gyllenhaal's Modern Slick Back - Versatile and AdaptableJake Gyllenhaal's Modern Slick Back – Versatile and Adaptable

Styling Guide for the Slick Back

  • Start with damp, towel-dried hair. Apply a small amount of pomade or hair gel, focusing from the roots to the ends.
  • Use a wide-toothed comb to slick the hair back, starting from the forehead and moving towards the crown.
  • For a glossier finish, use a fine-toothed comb to ensure a smooth, even look.
  • Blow-dry the hair back using a concentrator nozzle for a sleeker appearance. Finish with pomade or hair spray for added hold and shine.

Facial Hair Pairings

The slick back pairs exceptionally well with a clean-shaven face, emphasizing its sophisticated nature. However, a well-groomed beard or moustache can add a touch of masculinity and create a more contemporary, edgy look.

Recommended Products

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

Maintenance Tips

Regular trims are advised every 4 to 6 weeks to maintain the polished appearance of the slick back. Ensure your barber understands the style you’re aiming for and can tailor the cut to your hair type and face shape. Between 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. Ivy League Scholarly Chic Hairstyle for Men

Men's Ivy League Old Money HairstyleMen's Ivy League Old Money Hairstyle

The Ivy League hairstyle is a classic, preppy look that embodies refined scholarly elegance. It’s a timeless haircut characterized by a short, neat appearance with a subtle quiff at the front, precisely tapered sides, and a crisp side part.

The Old Money Pedigree of the Ivy League Haircut

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

Ivy League University Life in the 1930s and 1940s - Scholarly ChicIvy League University Life in the 1930s and 1940s – Scholarly Chic

An evocative image of Ivy League prep university life from the 1930s-1940s, illustrating the scholarly chic aesthetic.

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. It’s a hairstyle that speaks of intellectual prowess and social standing.

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

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

Celebrities Known for the Ivy League Scholarly Chic Hairstyle

  • John F. Kennedy: JFK’s Ivy League style haircut is an iconic representation of this classic look.
    John F. Kennedy's Iconic Ivy League Haircut - Presidential StyleJohn F. Kennedy's Iconic Ivy League Haircut – Presidential Style
  • Ryan Gosling: Gosling has often sported a modern interpretation of the Ivy League haircut, showcasing the style’s versatility and enduring appeal.
    Ryan Gosling's Modern Ivy League Cut - Versatile and TimelessRyan Gosling's Modern Ivy League Cut – Versatile and Timeless

Styling Guide for the Ivy League Haircut

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

Facial Hair Pairings

The Ivy League haircut is best complemented by a clean-shaven face, emphasizing the style’s neat, polished appearance and drawing attention to the hair’s clean lines and refined silhouette. However, a well-groomed moustache can be an excellent option for gentlemen seeking to add a touch of vintage charm and sophistication to their look. A neatly trimmed, classic moustache 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 a bygone era.

Recommended Products

Baxter of California Clay Pomade is a water-based pomade for a medium hold and matte finish, ideal for creating the Ivy League’s structured yet natural-looking style. American Crew Forming Cream, with a light to medium hold and low-shine finish, is perfect for achieving the Ivy League’s polished yet understated appearance. To keep your Ivy League haircut in place and protected against humidity and frizz, a lightweight hair spray like Oribe Superfine Hair Spray is a must-have.

Maintenance Tips

Maintaining the Ivy League haircut’s clean, structured appearance requires regular trims every 3 to 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 neat. The Ivy League haircut is a timeless old-money style that projects an air of intelligence, refinement, and understated elegance.

4. Taper Fade Hairstyle for Men

Men's Taper Fade Old Money HairstyleMen's Taper Fade Old Money Hairstyle

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

The Old Money Resonance of the Taper Fade

While the taper fade has gained prominence in recent years, its roots can be traced back to the classic, clean-cut hairstyles favored by the wealthy and influential throughout the 20th century. Gaining popularity in the 1940s, the taper fade’s emphasis on neatness, structure, and precision echoes the timeless values of the old-money aesthetic.

Historical Evolution of the Taper Fade HairstyleHistorical Evolution of the Taper Fade Hairstyle

A visual timeline showcasing the historical evolution of the taper fade hairstyle, from its classic origins to modern interpretations.

At the same time, its modern interpretation allows for greater flexibility and personal expression. The taper fade is a superb mix of traditional and contemporary styling, making it the go-to choice for gentlemen seeking to project elegance in both professional and social settings.

Hair Texture, Length, and Volume for the Taper Fade

The taper fade is remarkably versatile and can be adapted to suit a wide range of hair types, textures, and lengths. However, to achieve the most polished and refined results, starting with hair that has a medium to fine texture and a moderate amount of natural volume is best. The ideal length for the top portion of the hair depends on your personal styling goals, but a 1 to 4 inches range is generally recommended. This length allows for various styling options, from sleek and smooth to textured and tousled, while maintaining the taper fade’s signature blended appearance. Regarding volume, the goal 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 sleek, polished looks 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's Polished Taper Fade - Red Carpet ReadyJustin Timberlake's Polished Taper Fade – Red Carpet Ready
  • Ryan Reynolds: Reynolds’ clean-cut, yet slightly textured, looks exemplify how taper fades can be adapted to suit various personal styles and occasions, from red-carpet events to casual, everyday settings.
    Ryan Reynolds' Clean-Cut Taper Fade - Versatile for Any OccasionRyan Reynolds' Clean-Cut Taper Fade – Versatile for Any Occasion
  • Michael B. Jordan: Jordan’s taper fades and 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 that project an image of confidence and adaptability.
    Michael B. Jordan's Sharp Taper Fade - Confident and AdaptableMichael B. Jordan's Sharp Taper Fade – Confident and Adaptable

Styling Guide 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 while simultaneously using a round brush or your fingers to shape and style it in your preferred direction.
  • Once the top portion of your hair is dry and styled to your liking, 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 the look and ensure long-lasting hold, apply a small amount of hair spray or a light-hold styling product, such as a grooming cream or texture spray, to the hair on top.

Facial Hair Pairings

The taper fade’s versatility extends to its compatibility with various facial hairstyles, allowing gentlemen to customize their looks to suit their 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 moustache, carefully trimmed, shaped 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 Products

To achieve and maintain the perfect taper fade, using high-quality hair products that provide the right balance of hold, texture, and finish is essential. Some recommended options include: Hanz de Fuko Claymation, a matte-finish styling product that combines clay’s strength with wax’s flexibility, making it ideal for creating textured yet controlled taper fade styles. For gentlemen who prefer a sleeker, more polished taper fade, Uppercut Deluxe Pomade offers the perfect combination of medium hold and high shine. Baxter of California Clay Effect Style Spray is excellent when a lightweight, texturizing finish is desired.

Maintenance Tips

Depending on your hair’s natural growth rate and desired level of precision, scheduling barber appointments every 2 to 4 weeks is recommended to keep the taper fade looking its best.

5. Undercut Hairstyle for Men

Men's Undercut Old Money HairstyleMen's Undercut Old Money Hairstyle

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, starkly contrasting with longer hair on top. The undercut is a bold hairstyle for men who want to make a statement and stand out. It departs from traditional, conservative styles associated with the old-money aesthetic, appealing to those who embrace individuality and a modern edge.

The Old Money Juxtaposition of the Undercut

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

Historical Context of the Undercut HairstyleHistorical Context of the Undercut Hairstyle

A historical perspective on the undercut hairstyle, tracing its origins and evolution through different eras.

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. It’s a style that confidently bridges classic and contemporary worlds.

Hair Texture, Length, and Volume for the Undercut

The undercut is best suited for men with straight or slightly wavy hair, relying on the stark contrast between the short sides and the longer top to make its statement. The ideal length for the top portion is 2 to 5 inches, allowing for various styling options and dramatic volume. The sides and back are usually clipped very short, with a #1 or #2 guard, or even fully buzzed. The sharp distinction between the top and sides creates a bold, eye-catching silhouette.

Celebrities Known for Undercut Hairstyles

  • Brad Pitt: Pitt has sported various undercut styles, showcasing the hairstyle’s rugged, masculine appeal.
    Brad Pitt's Rugged Undercut - Masculine AppealBrad Pitt's Rugged Undercut – Masculine Appeal
  • 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's Edgy Undercut - Rock and Roll VibeAdam Levine's Edgy Undercut – Rock and Roll Vibe
  • 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's Vintage-Inspired Undercut - Peaky Blinders InfluenceCillian Murphy's Vintage-Inspired Undercut – Peaky Blinders Influence

Styling Guide for the Undercut

  • Start with clean, dry hair. 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 for extra volume and lift.
  • Apply a small amount of hairspray or texturizing spray to hold the style in place and add definition.

Facial Hair 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 Products

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 suitable for various textures and styles.

Maintenance Tips

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

6. Classic Pompadour Hairstyle for Men

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 impressive volume that commands attention. The pompadour is a daring choice for men who appreciate a bygone era’s refined, dapper aesthetics and is ideal for recalling the elegance and panache of classic Hollywood icons.

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

Elvis Presley and Johnny Cash Sporting Classic Pompadour HaircutsElvis Presley and Johnny Cash Sporting Classic Pompadour Haircuts

Left to right: Legendary musicians Elvis Presley and Johnny Cash showcasing classic pompadour hairstyles, iconic in their eras.

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. It’s a hairstyle that’s both bold and refined.

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 to 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's Legendary Pompadour - Iconic StyleElvis Presley's Legendary Pompadour – Iconic Style
  • James Dean: Dean’s effortlessly cool take on the pompadour helped cement the style’s association with rebellious, bad-boy charm.
    James Dean's Effortlessly Cool Pompadour - Rebellious CharmJames Dean's Effortlessly Cool Pompadour – Rebellious Charm
  • David Beckham: Beckham has sported a modern version of the pompadour, showcasing the style’s versatility and ongoing relevance in contemporary fashion.
    David Beckham's Modern Pompadour - Contemporary RelevanceDavid Beckham's Modern Pompadour – Contemporary Relevance

Styling Guide for the Pompadour

  • Start with damp, towel-dried hair. Apply a generous amount of high-hold pomade or styling cream, working it evenly through the hair.
  • Create a side part if desired using a comb, then sweep the hair on top upward and back, starting from the forehead and moving 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 Hair Pairings

A clean-shaven face is a traditional choice for the classic pompadour, highlighting the hairstyle’s crisp, polished appearance. However, a well-groomed moustache 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 Products

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 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 Tips

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

7. Quiff Hairstyle for Men

Men's Quiff Old Money HaircutMen's Quiff Old Money Haircut

The quiff is a modern hairstyle combining 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 Old Money Inspiration Behind the Quiff

While the quiff is a relatively modern hairstyle, it draws inspiration from the classic pompadour, which has 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 - Timeless CoolJames Dean 50s Quiff Haircut – Timeless Cool

James Dean sporting a 50s quiff haircut, a timeless symbol of cool and classic style inspiration.

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.

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 to 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 Known for Quiff Hairstyles

  • Zac Efron: Efron’s modern quiff features a textured, tousled top and shorter sides, showcasing the style’s youthful, effortless appeal.
    Zac Efron's Youthful Quiff - Effortless AppealZac Efron's Youthful Quiff – Effortless Appeal
  • 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's Sleek Quiff - Red Carpet SophisticationChris Pine's Sleek Quiff – Red Carpet Sophistication
  • 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's Classic Quiff with Side Part - Bridging Traditional and ModernDavid Gandy's Classic Quiff with Side Part – Bridging Traditional and Modern

Styling Guide for the Quiff

  • Begin with damp, towel-dried hair. Apply a small pre-styling mousse or volumizing spray for added lift and hold.
  • Use a blow dryer and a round brush to 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 Hair 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 moustache or goatee, which can complement the hairstyle’s classic and contemporary elements.

Recommended Products

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 Tips

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

8. Crew Cut Hairstyle for Men

Men's Military Crew Cut HaircutMen's Military Crew Cut Haircut

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 Old Money Simplicity of the Crew Cut

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

Historical Crew Cut Styles for MenHistorical Crew Cut Styles for Men

Men’s crew cut hairstyles in the 1920s and 1930s, reflecting an era of practicality and understated style.

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. It’s a haircut that speaks of efficiency and timelessness.

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 Known for Crew Cut Haircuts

  • Ryan Reynolds: Reynolds often sports a classic crew cut, showcasing the style’s timeless appeal and ability to complement various face shapes.
    Ryan Reynolds Sporting a Classic Crew CutRyan Reynolds Sporting a Classic 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's Modern Textured Crew CutTom Hardy's Modern Textured 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's Versatile Crew Cut - From Casual to FormalChanning Tatum's Versatile Crew Cut – From Casual to Formal

Styling Guide for the Crew Cut

  • Start with a small amount of matte pomade or styling cream on clean, damp hair. Apply from the top down, distributing it evenly with your fingers.
  • Style the hair on top forward, to the side, or in a slightly messy, textured manner using a comb or your fingers, 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 Hair 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 moustache or goatee, which can complement the hairstyle’s simple but refined nature.

Recommended Products

To maintain the crew cut’s neat appearance and add a touch of texture or definition, consider using American Crew Forming Cream, which provides a pliable, low-shine hold that helps to tame and style short hair, or Baxter of California Clay Pomade for a matte, textured finish with a strong, pliable hold.

Maintenance Tips

To keep your crew cut looking sharp and well-maintained, schedule regular barber visits every 2 to 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.

9. Buzz Cut for Men

Men's Classic Buzz Cut HairstyleMen's Classic Buzz Cut Hairstyle

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 Old Money Pragmatism of the Buzz Cut

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 and make it a timeless, classic choice for men across various social and economic backgrounds.

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 Known for Buzz Haircuts

  • 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.
    David Beckham's Buzz Cut - Versatile and StylishDavid Beckham's Buzz Cut – Versatile and Stylish
  • 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's Modern Edgy Buzz CutZayn Malik's Modern Edgy Buzz Cut
  • 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 Guide 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 Hair 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. These can complement the hairstyle’s simple yet confident nature.

Recommended Products

Due to the buzz cut’s short length, minimal product is needed to maintain the style. However, American Crew Firm Hold Gel, which provides a strong, non-flaking hold with a low shine, and Baxter of California Grooming Cream, a lightweight, nourishing formula that moisturizes the scalp and adds a subtle, matte finish, can be used for added control and scalp health.

Maintenance Tips

To maintain the buzz cut’s neat, uniform appearance, schedule regular barber visits every 2 to 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, ideal for men who value a no-nonsense approach to grooming while still maintaining a stylish look.

10. Comb Over Hairstyle for Men

Men's Comb Over Old Money Style HaircutMen's Comb Over Old Money Style Haircut

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 Old Money Lineage of the Comb Over

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.

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 to 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 to 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 Known for Comb Over Haircuts

  • 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's Classic Comb Over - Refined SophisticationGeorge Clooney's Classic Comb Over – Refined 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.
  • 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's Versatile Comb Over - Complementing Various StylesLeonardo DiCaprio's Versatile Comb Over – Complementing Various Styles

Styling Guide 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.
  • Use a blow dryer and a round brush to 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 Hair 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 moustache, which can complement the hairstyle’s blend of classic and modern elements.

Recommended Products

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 Tips

To keep your comb sharp and well-maintained, schedule regular barber visits every 3 to 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. French Crop Hairstyle for Men

Men's French Crop Fringe HaircutMen's French Crop Fringe Haircut

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 Old Money Understated Charm 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 emphasis on simplicity align with old-money values. The Caesar cut originated in ancient Rome and was popularized by the Roman emperor Julius Caesar, becoming 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.

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 to 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, maintaining an understated elegance.

Celebrities Known for French Crop Haircuts

  • 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's French Crop - Period Drama AdaptabilityCillian Murphy's French Crop – Period Drama Adaptability
  • 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 Guide 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 Hair 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 Products

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 Tips

To keep your French crop looking sharp and well-defined, schedule regular barber visits every 3 to 4 weeks to maintain the proper length on top and neatly trim the back and sides.

12. Side Fringe Hairstyle for Men

Men's Side Fringe HaircutMen's Side Fringe Haircut

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 Old Money Evolution of the Side Fringe

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.

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 Known for 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's Effortlessly Cool Side FringeTimothée Chalamet's Effortlessly Cool Side Fringe
  • 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 Guide 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, piece appearance.
  • For a more relaxed, tousled look, use your fingers to gently mess up the fringe and add a carefree, lived-in vibe.

Facial Hair 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 Products

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 Tips

To keep your side fringe looking fresh and well-defined, schedule regular barber visits every 4 to 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, appealing to younger men who want to embrace a more relaxed, contemporary aesthetic while still nodding to the timeless tradition of the side-swept style.

13. Regulation Cut Hairstyle for Men

Men's Regulation Cut HaircutMen's Regulation Cut Haircut

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 Old Money Discipline of the Regulation Cut

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.

Historical Military Regulation Cut StylesHistorical Military Regulation Cut Styles

Historical images of military regulation cut hairstyles, reflecting discipline and adherence to strict grooming standards.

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.

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 Known for Regulation Cuts

  • 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's Military Regulation Cut - Tough MasculinityJake Gyllenhaal's Military Regulation Cut – Tough Masculinity
  • 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 Guide 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 Hair 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, 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 Products

Given the regulation cut’s extremely short length and low-maintenance nature, minimal product is needed to maintain the style. However, American Crew Fiber, a matte-finish, high-hold product, and Baxter of California Super Close Shave Formula, a soothing, lubricating shave cream, can be used for added texture on top and for maintaining a clean shave around the haircut.

Maintenance Tips

Frequent barber visits are essential to maintaining the precise, uniform appearance of the regulation cut. Schedule appointments every 1 to 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.

14. Short Curtain Hairstyle for Men

Men's Short Curtain HaircutMen's Short Curtain Haircut

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 Old Money Nostalgia of the Short Curtain

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 90s Short Curtain HairLeonardo DiCaprio and Johnny Depp 90s Short Curtain Hair

From left to right: Johnny Depp and Leonardo DiCaprio showcasing the iconic 90s short curtain haircut, a symbol of retro style.

While not directly associated with old-money fashion historically, 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. It’s a style that borrows from the past while remaining relevant today.

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 Known for Short Curtain Haircuts

  • 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's Tousled Short Curtain - Versatile CustomizationCharles Melton's Tousled Short Curtain – Versatile Customization
  • 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 Guide 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.
  • Create a middle part using a comb, 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 on 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, being careful not to disrupt the hair’s natural fall.

Facial Hair 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 Products

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

Maintenance Tips

To keep your short curtain hairstyle fresh and well-maintained, schedule regular barber visits every 4 to 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. Edgar Haircut for Men

Men's Classic Edgar HaircutMen's Classic Edgar Haircut

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 Old Money Rebelliousness of the Edgar

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. It’s a style that breaks the mold while still valuing precision and intentionality.

Hair Texture, Length, and Volume for the Edgar

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. 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 Known for Edgar Haircuts

  • 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's Sleek Edgar - Sporty and YouthfulKylian Mbappé's Sleek Edgar – Sporty and Youthful
  • 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's Edgy Edgar - Fashion Forward VibeAnwar Hadid's Edgy Edgar – Fashion Forward Vibe
  • 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 Guide for the Edgar

  • 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.
  • Style the hair on top forward or upward using a comb or your fingers, 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 Hair 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 Products

To achieve and maintain the perfect Edgar haircut, consider using Hanz de Fuko Heavymade Pomade, a high-hold, water-based pomade with a strong, long-lasting hold and a natural, satin finish, or Layrite Cement Matte Hair Clay, a pliable, matte-finish clay with a strong, texturizing hold.

Maintenance Tips

Frequent barber visits are essential to maintaining the Edgar haircut’s precise, angular appearance. Schedule appointments every 2 to 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 age. Understanding these elements will help you select a hairstyle that not only looks sophisticated but also suits your individual needs and preferences.

Old Money Style Grooming and Hair EssentialsOld Money Style Grooming and Hair Essentials

Essential grooming and hair styling elements for achieving a polished old money style, showcasing attention to detail.

Face Shape Considerations

Understanding your face shape is crucial when choosing a hairstyle that flatters your features and enhances your overall appearance. Here is a simple and quick quiz to help you determine your face shape. The main face shapes include:

Oval Face Shape: Characterized by a slightly longer length than width, with a rounded jawline and a forehead that is slightly wider than the chin. Most hairstyles work well with this versatile face shape, so focus on styles that maintain the face’s natural balance and proportion.

Round Face Shape: Nearly equal in length and width, with a soft, curved jawline and no prominent angles. Opt for hairstyles that add height and volume on top while keeping the sides and back short to elongate the face and create a more angular appearance.

Square Face Shape: Defined by a strong, angular jawline and a forehead approximately the same width as the chin. Choose styles that soften the strong angles of the jawline, such as those with shorter sides and a slightly longer, textured top.

Heart Face Shape: Wider at the forehead and cheekbones, narrowing down to a pointed chin. Select hairstyles that balance the wider forehead and narrower chin, such as those with side-swept fringes or a medium-length top with shorter sides.

Diamond Face Shape: 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 close to the head at the cheekbones to minimize width.

Hair Type and Texture

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

Straight Hair: Naturally smooth and flat, with no discernible curl or wave. Most old-money hairstyles work well with straight hair, making achieving a sleek, polished appearance easier. Focus on styles that add volume and texture to prevent the hair from looking flat or lifeless.

Wavy Hair: Falls in loose, S-shaped curves, more defined than straight hair but less than 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: Forms tight, defined ringlets or coils from the scalp to the ends. Opt for old-money hairstyles that work with 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: Characterized by very tight, densely packed curls or coils that may have a zig-zag or Z-shaped pattern. Select hairstyles that embrace 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 Commitment

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.

For a busy lifestyle or a low-key grooming approach, opt for low-maintenance old-money hairstyles such as the Buzz Cut, Crew Cut, French Crop, and Regulation Cut. These styles typically require less frequent barber visits and can be styled quickly with minimal product.

For those who enjoy a more involved grooming routine and appreciate the process of styling, consider old-money hairstyles that offer more customization and experimentation opportunities, such as the Classic Side Part, Slick Back, Quiff, and Classic Pompadour. These styles often require more frequent trims, daily styling with specific products, and more time and effort to achieve the desired look.

Old-Money Hairstyles by Age Groups

While old-money hairstyles are timeless and can be worn by men of all ages, certain hairstyles may be perceived as more suitable for specific age groups.

Younger Men (18-30): Younger men have the most flexibility in experimenting with old-money hairstyles and can often pull off bolder, more contemporary looks without appearing out of place. Styles like the Quiff, Undercut, French Crop, and Short Curtain work particularly well, offering a balance of classic sophistication and modern edge.

Middle-Aged Men (31-50): For middle-aged men, focus on old-money hairstyles that convey maturity, refinement, and established success. Styles like the Classic Side Part, Taper Fade, Ivy League, and Comb Over offer a polished, sophisticated appearance well-suited to professional and social settings.

Older Men (51+): For older men, choose age-appropriate, flattering, and easy-to-maintain old-money hairstyles. Styles like the Ivy League, Regulation Cut, Classic Side Part (with a slightly longer top), and Short Crew Cut offer a timeless, distinguished appearance that embraces natural changes in hair texture and density while projecting refinement and sophistication.

Final Thoughts

The old money aesthetic, deeply rooted in traditional values and understated wealth, offers a confident look of timeless elegance and silent affluence. In a world of fast fashion trends and new money statements, the old-money aesthetic remains a bastion of steadfast refinement. An old-money haircut is central to achieving this distinguished look, providing a fast and effective way to project an image of timeless elegance, refined sophistication, and rich heritage. The key to choosing the right old-money haircut is to consider your features, lifestyle, and personal preferences, selecting a style that makes you feel confident, comfortable, and authentic.

Style Like a True Gentleman

Professional styling requires knowing your unique body shape and seasonal color palette, paramount factors in choosing perfectly fitting clothes in colors that complement your natural features. Only then can a stylist engage in styling by occasion, location, season, and time of day, with garments, footwear, and accessories from stylistically relevant heritage fashion brands to depict high confidence and success.

Find your body shape, seasonal color palette, and ideal fashion style in less than 5 minutes for free with our four simple steps:

1. Find Your Body Shape: Take our free body shape quiz for men to discover which garments flatter your silhouette.

2. Find Your Unique Color Palette: Use our free seasonal color quiz for men to ensure your clothing hues complement your natural coloring.

3. Find Your Ideal Fashion Style: Discover your ideal personal fashion style with our free fashion style quiz for men, including outfit ideas and brand recommendations.

4. Professional Image Consultancy with The VOU: For expert styling by occasion, location, season, and time of day, our image consultants and fashion stylists at The VOU offer comprehensive and detailed styling services for men. Contact us today for a free initial styling assessment to dress like a confident, successful gentleman of exquisite fashion taste.

   #####  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.

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