Classic Side Part Old Money Hairstyle
Classic Side Part Old Money Hairstyle

Old Money Haircut: Timeless Styles for a Refined Look

The “old money haircut” embodies a sense of understated elegance and classic sophistication, often associated with affluence and heritage. These hairstyles are characterized by their clean lines, meticulous grooming, and enduring appeal. They project an image of quiet confidence and refined taste, moving beyond fleeting trends to embrace timeless style.

Key Considerations for Old Money Haircuts

  • Match to Face Shape and Hair Texture: Selecting a haircut that complements your individual features is paramount for achieving a balanced and flattering look.
  • Lifestyle and Upkeep: Consider how much time and effort you’re willing to dedicate to daily styling and maintenance. Some styles require more frequent barber visits and product use than others.
  • Age Appropriateness: While classic styles are generally timeless, certain haircuts may resonate more strongly with specific age groups, contributing to a harmonious and sophisticated overall appearance.

Eager to explore the world of old money haircuts? Continue reading to discover the top styles that exude timeless refinement.

1. The Classic Side Part: Epitome of Timeless Elegance

Classic Side Part Old Money HairstyleClassic Side Part Old Money Hairstyle

The classic side part haircut is a quintessential embodiment of old money style. It’s defined by a crisp, precisely defined part that cleanly divides the hair, typically extending from the crown to the temple. The hair on top is left slightly longer than the sides, which are neatly tapered or faded to create a polished and structured silhouette.

The Old Money Appeal of the Classic Side Part

Emerging in the sophisticated eras of the 1920s and 1930s, the classic side part quickly became a hallmark of refined masculinity. Hollywood icons like Cary Grant and Fred Astaire championed this style, moving away from the slicked-back, longer styles of previous decades. It became a visual representation of order, discipline, and understated wealth, core tenets of the old money aesthetic.

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

The clean, structured nature of the classic side part conveys an image of meticulous grooming and attention to detail, resonating deeply with the values of the old money style.

Ideal Hair Type, Length, and Volume

The classic side part is best suited for men with medium to fine hair textures, particularly those with a slight natural wave which adds subtle movement and avoids a too-stiff appearance.

For length, the top section should be approximately 2-4 inches, sufficient to comb over and maintain the defined part. The sides should be shorter, in the range of 0.5 to 1 inch, for a clean and balanced contrast. Volume should be controlled and structured, avoiding excessive stiffness or heaviness to maintain the style’s refined silhouette.

Celebrities Embracing the Classic Side Part

  • Jon Hamm: His portrayal of Don Draper in “Mad Men” solidified the classic side part as a symbol of mid-century masculine style, becoming a modern benchmark for this timeless haircut.

Jon Hamm Classic Side Part Old Money HairstyleJon Hamm Classic Side Part Old Money Hairstyle

  • George Clooney: Clooney’s silver fox side part is a distinguished example, demonstrating the enduring appeal of this cut across generations. His mature take exemplifies sophistication and timeless charm.

George Clooney Classic Side Part Old Money HairstyleGeorge Clooney Classic Side Part Old Money Hairstyle

  • David Beckham: Beckham has frequently sported variations of the classic side part, demonstrating its adaptability and enduring relevance in contemporary men’s style.

David Beckham Classic Side Part Old Money HairstyleDavid Beckham Classic Side Part Old Money Hairstyle

  • Ryan Gosling: Gosling’s version often features a slightly longer top and a more textured finish, offering a relaxed yet still refined take on the traditional side part.

Ryan Gosling Classic Side Part Old Money HairstyleRyan Gosling Classic Side Part Old Money Hairstyle

Styling Guide for the Classic Side Part

  1. Start with Damp Hair: Begin with towel-dried hair.
  2. Apply Styling Product: Use a small amount of pomade or styling cream, working it from the roots to the ends.
  3. Create the Part: With a fine-toothed comb, create a sharp, defined part from the crown to your temple.
  4. Blow Dry and Shape: Blow-dry the top hair towards the part, using a round brush to add volume and smoothness.
  5. Refine the Style: For a less formal look, gently tousle the top hair with your fingers while maintaining the part’s structure.

Facial Hair Pairings

The classic side part is traditionally paired with a clean-shaven face, accentuating its polished and sharp aesthetic. However, a meticulously groomed moustache or a neatly trimmed beard can also complement the style, adding a touch of vintage charm or contemporary sophistication.

Recommended Products

  • Baxter of California Hard Water Pomade: Offers a medium to firm hold with a slight sheen, perfect for a classic finish.
  • Creed Green Irish Tweed Hair Pomade: A luxury option providing excellent hold and a subtle, sophisticated fragrance.
  • R+Co Outer Space Flexible Hairspray: A lightweight hairspray for added hold and frizz control without stiffness.

Maintenance Schedule

To maintain the classic side part’s crisp appearance, regular trims every 3-4 weeks are crucial. Communicate clearly with your barber about the desired style and ensure they understand how to tailor the cut to your face shape and hair type. Daily touch-ups and restyling will keep the look sharp between barber visits.

The classic side part remains a cornerstone of old money hairstyles, offering a versatile and timeless look suitable for various face shapes and personal styles.

2. The Slick Back: Effortless Sophistication

Slick Back Old Money HairstyleSlick Back Old Money Hairstyle

The slick back hairstyle is a timeless and sophisticated choice, exuding an air of tasteful refinement. It’s achieved by brushing the hair directly back and away from the forehead, creating a smooth, sleek appearance. This style is synonymous with confidence and polished charm.

The Old Money Lineage of the Slick Back

The slick back gained significant popularity in the 1920s and 1930s, during Hollywood’s Golden Age. Icons like Clark Gable and Humphrey Bogart popularized this look, making it a symbol of the suave and sophisticated gentleman. Its association with this era and these figures cements its place in the old money aesthetic.

Clark Gable and Humphrey Bogart Slick Back Old Money HairstyleClark Gable and Humphrey Bogart Slick Back Old Money Hairstyle

The slick back’s appeal within the old money style lies in its ability to project confidence, refinement, and an effortless sense of style. It speaks to a man who is in control and appreciates classic aesthetics.

Ideal Hair Type, Length, and Volume

The slick back works best with medium to thick hair types, ideally with a slight natural wave or straight texture. This hair type provides the necessary substance and control for the style.

Hair length for the top should be approximately 3-5 inches, allowing enough length to comb back smoothly and maintain the style. Sides and back should be shorter, around 1-2 inches, to keep the focus on the sleek top. Volume should be balanced to achieve a smooth, sleek look without appearing flat or lifeless.

Celebrities Known for the Slick Back

  • Leonardo DiCaprio: His slick back in “The Great Gatsby” perfectly captured the old money charm and sophistication of the Roaring Twenties, making it a defining style moment.

Leonardo DiCaprio Slick Back Old Money HairstyleLeonardo DiCaprio Slick Back Old Money Hairstyle

  • Michael Douglas: Douglas’s slick back embodies mature sophistication, demonstrating how this style can remain elegant and impactful across different age groups.

Michael Douglas Slick Back Old Money HairstyleMichael Douglas Slick Back Old Money Hairstyle

  • Jake Gyllenhaal: Gyllenhaal often sports a modern slick back, showcasing its versatility and ability to be adapted for contemporary styles while retaining its classic essence.

Jake Gyllenhaal Slick Back Old Money HairstyleJake Gyllenhaal Slick Back Old Money Hairstyle

Styling Guide for the Slick Back

  1. Damp Hair Preparation: Start with damp, towel-dried hair.
  2. Apply Styling Product: Use a pomade or hair gel, focusing on the roots and distributing evenly to the ends.
  3. Comb Backwards: Use a wide-toothed comb to slick the hair straight back from the forehead towards the crown.
  4. Refine for Gloss: For a high-gloss finish, use a fine-toothed comb to smooth and refine the surface.
  5. Blow Dry for Sleekness: Use a blow dryer with a concentrator nozzle, directing airflow backwards for a sleeker finish. Finish with more pomade or hair spray for added hold and shine.

Facial Hair Pairings

The slick back is traditionally paired with a clean-shaven face, emphasizing its sophisticated and polished appearance. However, a well-groomed beard or moustache can introduce a touch of masculinity and create a more modern, edgy variation of the look.

Recommended Products

  • Layrite Super Hold Pomade: Known for its strong hold and high shine, ideal for a classic slick back.
  • Suavecito Firme Hold Pomade: Another excellent strong-hold pomade with high shine, popular for achieving a traditional slicked style.
  • American Crew Firm Hold Styling Gel: Provides a sleek, wet-look finish with a strong hold, suitable for a more dramatic slick back.

Maintenance Schedule

Regular trims every 4-6 weeks are recommended to maintain the slick back’s polished appearance. Ensure your barber understands the style and can tailor the cut to your hair type and face shape. Daily restyling is essential to maintain the slicked-back look, requiring consistent product application and technique.

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 and Refined

Ivy League Old Money HairstyleIvy League Old Money Hairstyle

The Ivy League haircut embodies scholarly chic, projecting an image of refined elegance and intellectual prowess. It’s a classic, preppy look characterized by a short, neat appearance with a subtle quiff at the front, sharply tapered sides, and a clean side part.

The Old Money Roots of the Ivy League

Named after the prestigious Ivy League universities in the United States like Harvard, Yale, and Princeton, this style emerged in the 1920s. It gained popularity among the young, affluent men attending these institutions, becoming synonymous with elite education and a sophisticated lifestyle.

Ivy League Prep University Life 1930s 1940sIvy League Prep University Life 1930s 1940s

The Ivy League haircut’s association with these bastions of wealth, power, and influence firmly establishes it within the old money aesthetic. It’s a haircut that speaks of heritage, education, and understated status.

Ideal Hair Type, Length, and Volume

Fine to medium hair with a slight natural wave is ideal for the Ivy League haircut. This texture allows for a neat, structured appearance with natural movement.

The top should be relatively short, around 1-2 inches, just enough to create a subtle quiff at the front. Sides and back should be tapered shorter, fading from about 1 inch at the top to approximately 0.5 inches near the ears and neckline. This precise tapering ensures crisp lines and a refined silhouette, crucial for the Ivy League look.

Celebrities Sporting the Ivy League

  • John F. Kennedy: Perhaps the most iconic example, JFK’s Ivy League haircut became synonymous with presidential style and classic American elegance.

John F. Kennedy Ivy League HairstyleJohn F. Kennedy Ivy League Hairstyle

  • Ryan Gosling: Gosling often sports a modern interpretation of the Ivy League, demonstrating its versatility and enduring appeal in contemporary settings.

Ryan Gosling Ivy League HairstyleRyan Gosling Ivy League Hairstyle

Styling Guide for the Ivy League

  1. Damp Hair Application: Start with slightly damp hair.
  2. Apply Product Lightly: Use a small amount of pomade or styling cream, working it through from roots to ends with your fingers.
  3. Create Side Part: Use a fine-toothed comb to create a crisp side part from the crown towards the temple.
  4. Blow Dry and Quiff: Blow dry the top on medium heat, using a small round brush to create volume and a subtle quiff at the front.
  5. Refine the Quiff: Once dry, refine the quiff with fingers or a comb for a neat, structured finish.

Facial Hair Pairings

The Ivy League haircut is best complemented by a clean-shaven face, emphasizing its neat, polished appearance and drawing attention to the haircut’s clean lines and refined silhouette. However, a well-groomed moustache can add a touch of vintage charm and sophistication, particularly a classic style like the chevron or pyramidal.

Recommended Products

  • Baxter of California Clay Pomade: A water-based pomade offering medium hold and a matte finish, ideal for the Ivy League’s structured yet natural look.
  • American Crew Forming Cream: Provides light to medium hold and a low-shine finish, perfect for achieving the style’s polished yet understated appearance.
  • Oribe Superfine Hair Spray: A lightweight hairspray to keep the style in place and protect against humidity and frizz.

Maintenance Schedule

Maintaining the Ivy League’s clean, structured appearance requires trims every 3-4 weeks. This frequency ensures the top remains at the ideal length for the subtle quiff and keeps the tapered sides and back neat. Regular barber visits are crucial to preserve this style’s refined aesthetic.

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

4. The Taper Fade: Modern Refinement with Classic Roots

Taper Fade Old Money HairstyleTaper Fade Old Money Hairstyle

The taper fade is a contemporary hairstyle that seamlessly blends classic elegance with modern, clean-cut aesthetics. It appeals to today’s discerning gentlemen seeking a refined yet current look. This haircut features a gradual taper from longer lengths on 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 surged in popularity recently, its origins can be traced back to the clean-cut styles favored by the wealthy and influential throughout the 20th century, particularly gaining traction in the 1940s. Its emphasis on neatness, structure, and precision aligns with the timeless values of the old money aesthetic.

Taper Fade Hairstyle HistoryTaper Fade Hairstyle History

The taper fade offers a modern interpretation that allows for greater flexibility and personal expression while maintaining a connection to classic grooming. It’s a go-to choice for gentlemen seeking to project elegance in both professional and social environments, bridging traditional and contemporary styling.

Ideal Hair Type, Length, and Volume

The taper fade is remarkably versatile, adaptable to a wide range of hair types, textures, and lengths. However, for the most polished and refined results, medium to fine hair with moderate natural volume is ideal.

The top length can vary based on styling preferences, generally ranging from 1-4 inches. This range allows for diverse styling options, from sleek to textured, while maintaining the fade’s blended appearance. Volume should be balanced to complement facial features and head shape proportionally.

Celebrities Known for the Taper Fade

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

Justin Timberlake Taper Fade Old Money HairstyleJustin Timberlake Taper Fade Old Money Hairstyle

  • Ryan Reynolds: Reynolds’ clean-cut, yet slightly textured taper fades exemplify how the style can be tailored for different personal aesthetics and settings, from formal events to everyday wear.

Ryan Reynolds Taper Fade Old Money HairstyleRyan Reynolds Taper Fade Old Money Hairstyle

  • Michael B. Jordan: Jordan’s taper fades are often characterized by precise, graduated cuts with crisp lines and sharp fades, highlighting his features. The longer top allows for various stylish, textured looks, projecting confidence and adaptability.

Michael B. Jordan Taper Fade Old Money HairstyleMichael B. Jordan Taper Fade Old Money Hairstyle

Styling Guide for the Taper Fade

  1. Clean, Damp Hair: Start with clean, towel-dried hair washed with quality shampoo and conditioner.
  2. Apply Styling Product: Apply a small amount of pomade, clay, or cream to the top, working from roots to ends.
  3. Blow Dry and Shape: Blow dry the top on medium heat, using a round brush or fingers to shape and style in your preferred direction.
  4. Blend Top and Sides: Use a fine-toothed comb or soft-bristled brush to gently blend the longer top hair with the tapered sides and back.
  5. Finish with Hold: Apply a light hairspray or grooming cream for long-lasting hold.

Facial Hair Pairings

The taper fade’s versatility extends to facial hairstyles. A clean-shaven face enhances the clean cut, creating a refined appearance that emphasizes the taper fade’s structured silhouette. Alternatively, a well-groomed moustache, beard, or precisely styled stubble can enhance the old money aesthetic while allowing for personal expression.

Recommended Products

  • Hanz de Fuko Claymation: A matte-finish styling product combining clay and wax, ideal for textured yet controlled taper fade styles.
  • Uppercut Deluxe Pomade: Offers medium hold and high shine, perfect for a sleeker, more polished taper fade.
  • Baxter of California Clay Effect Style Spray: Excellent for a lightweight, texturizing finish.

Maintenance Schedule

Barber appointments every 2-4 weeks are recommended, depending on hair growth and desired precision. Regular maintenance is key to keeping the taper fade sharp and aligned with the old money aesthetic of meticulous grooming.

The taper fade is a modern classic that retains the refined essence of old money hairstyles, offering a versatile and elegant option for contemporary gentlemen.

5. The Undercut: Bold Confidence with a Nod to Tradition

Undercut Old Money HairstyleUndercut Old Money Hairstyle

The undercut is a striking, modern hairstyle that combines the refined appeal of old money aesthetics with a contemporary, daring twist. This attention-grabbing look features short, buzzed sides and back, contrasting sharply with longer hair on top. It’s a bold choice for men who want to make a statement while still hinting at classic sophistication.

The Unexpected Old Money Link to the Undercut

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

Undercut HistoryUndercut History

The undercut’s sharp contrast and precise lines echo the clean-cut, well-groomed appearance associated with the old money aesthetic, while its boldness pushes the boundaries of traditional styling. This juxtaposition makes it a unique and compelling choice within the old money spectrum.

Ideal Hair Type, Length, and Volume

The undercut is best suited for men with straight or slightly wavy hair, as the style relies on the stark contrast between the short sides and longer top.

The top portion should be 2-5 inches long, allowing for various styling options and dramatic volume. Sides and back are typically clipped very short, with a #1 or #2 guard, or even fully buzzed. This sharp distinction creates the undercut’s signature bold silhouette.

Celebrities Embracing the Undercut

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

Brad Pitt Undercut Old Money HaircutBrad Pitt Undercut Old Money Haircut

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

Adam Levine’s edgy yet polished 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, bridging historical and modern aesthetics.

Cillian Murphy’s vintage-inspired undercut haircut as Tommy Shelby in Peaky Blinders

Styling Guide for the Undercut

  1. Clean, Dry Hair: Start with clean, dry hair.
  2. Apply High-Hold Product: Apply a small amount of high-hold pomade or styling clay to the longer top hair.
  3. Style the Top: Style the top in your desired direction, creating volume, texture, and movement using a wide-toothed comb or fingers.
  4. Blow Dry for Volume: Use a blow dryer on medium heat, directing airflow at the roots while styling for extra lift.
  5. Finish with Hold: Apply hairspray or texturizing spray to hold the style and add definition.

Facial Hair Pairings

The undercut’s edgy, masculine appeal pairs well with 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. Neatly trimmed stubble or a short, well-defined beard can strike a balance, offering a rugged yet refined look.

Recommended Products

  • Layrite Cement Clay: Provides a firm, pliable hold with a natural, matte finish, ideal for textured undercut styles.
  • Suavecito Oil-Based Pomade: Offers superior hold and long-lasting control with a classic, slick look and high shine.
  • Kevin Murphy Rough Rider: A strong-hold clay with a matte finish, versatile for various textures and undercut styles.

Maintenance Schedule

Maintain the undercut’s sharp appearance with regular barber visits every 2-3 weeks. Consistent maintenance is crucial to preserve the distinct contrast between the short sides and longer top. Daily restyling with quality hair products will keep the undercut looking its best.

The undercut is a bold yet refined hairstyle that offers a modern take on old money aesthetics, perfect for men seeking a confident and distinctive look.

6. The Classic Pompadour: Vintage Charm and Volume

Classic Pompadour Old Money Hairstyle MenClassic Pompadour Old Money Hairstyle 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. It’s a daring yet elegant choice for men who appreciate the refined, dapper aesthetics of a bygone era.

The Rich History of the Pompadour in Old Money Style

With a history dating back to the 18th century, the pompadour is named after Madame de Pompadour, mistress of King Louis XV of France. It gained widespread popularity in the 1950s and 1960s, embraced by influential musicians and celebrities like Elvis Presley and Johnny Cash, becoming a symbol of rebellious elegance and charisma.

Elvis Presley and Johnny Cash Classic Pompadour HaircutElvis Presley and Johnny Cash Classic Pompadour Haircut

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 perfectly with old money sensibilities. It’s a statement of bold refinement and vintage charm.

Ideal Hair Type, Length, and Volume

Medium to thick hair with a slight natural wave is ideal for a classic pompadour. This hair type provides the necessary volume and structure.

The top hair should be long enough to create the signature swept-up look, typically 3-5 inches. Sides and back are kept shorter, usually tapered or faded, to emphasize the contrast and height of the pomp. Achieving a balance of volume and control is key, ensuring the style looks impressive but not overly stiff, maintaining its refined elegance.

Celebrities Known for the Pompadour

  • Elvis Presley: Presley’s legendary pompadour became a defining feature of his iconic style, inspiring generations to emulate his look. His pompadour is arguably the most famous and influential.

Elvis Presley Classic Pompadour Old Money HairstyleElvis Presley Classic Pompadour Old Money Hairstyle

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

James Dean Classic Pompadour Old Money HairstyleJames Dean Classic Pompadour Old Money Hairstyle

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

David Beckham Pompadour Old Money HairstyleDavid Beckham Pompadour Old Money Hairstyle

Styling Guide for the Classic Pompadour

  1. Damp Hair Preparation: Start with damp, towel-dried hair.
  2. Apply High-Hold Product Generously: Apply a generous amount of high-hold pomade or styling cream, distributing it evenly.
  3. Comb and Sweep Upward: Using a comb, create a side part if desired, then sweep the top hair upward and back from the forehead towards the crown.
  4. Blow Dry for Volume: Use a blow dryer on medium-high heat, directing airflow at the roots while combing back to create volume and height.
  5. Refine the Shape: Once shaped, refine with fingers or a comb for a smooth, polished finish.

Facial Hair Pairings

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

Recommended Products

  • Layrite Super Hold Pomade: Provides a water-based, high-hold formula to keep the pompadour in place all day.
  • Baxter of California Hard Cream Pomade: Offers a more natural, pliable hold with a subtle sheen, ideal for a softer pompadour.
  • Suavecito Firme Hold Pomade: Provides strong, long-lasting hold with high shine, perfect for a traditional, slick pompadour.

Maintenance Schedule

Regular barber visits every 3-4 weeks are crucial for maintaining the pompadour’s precise shape and neatly trimmed sides and back. Daily styling with appropriate products is necessary to ensure the pomp retains its volume and structure, reflecting the high-maintenance nature of this sophisticated style.

The classic pompadour is a timeless old money hairstyle, offering a blend of vintage sophistication, volume, and undeniable charm.

7. The Quiff: Modern Volume with Classic Inspiration

Quiff Old Money HaircutQuiff Old Money Haircut

The quiff is a modern hairstyle that skillfully combines elements of the classic pompadour with 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 Heritage of the Quiff

While the quiff is a relatively modern hairstyle, it draws direct inspiration from the classic pompadour, which has deep roots in old money fashion. Popularized by figures like 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 HaircutJames Dean 50s Quiff Haircut

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 Type, Length, and Volume

The quiff works best with medium to thick hair, with a slight natural wave or straight texture. This hair type provides the necessary volume and manageability for the style.

The top portion should be 2-4 inches long, allowing for enough volume and height to create the signature quiff shape. Sides and back should be shorter, typically between 0.5 and 2 inches, depending on the desired contrast and personal preference. The quiff’s volume can be customized from understated and textured to bold and high-volume.

Celebrities Known for the Quiff

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

Zac Efron quiff old money hairstyleZac Efron quiff old money 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, bridging classic and modern elegance.

Chris Pine Quiff Old Money HairstyleChris Pine Quiff Old Money Hairstyle

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

David Gandy Quiff Old Money HairstyleDavid Gandy Quiff Old Money Hairstyle

Styling Guide for the Quiff

  1. Damp Hair and Pre-Styling: Begin with damp, towel-dried hair and apply a pre-styling mousse or volumizing spray for added lift and hold.
  2. Blow Dry for Volume: Use a blow dryer and a round brush to dry the top hair up and back, focusing on creating volume at the roots and a smooth, curved shape.
  3. Apply Styling Product: Apply a small amount of pomade, clay, or styling cream, working it through with fingers to add texture, definition, and hold.
  4. Refine Texture: For a relaxed, tousled look, gently break up the quiff with fingers for 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. A neatly trimmed moustache or goatee can also complement the hairstyle’s blend of classic and contemporary elements for a balanced look.

Recommended Products

  • Hanz de Fuko Claymation: Provides pliable, long-lasting hold with a natural, matte finish, ideal for textured, modern quiffs.
  • Imperial Barber Classic Pomade: A water-based pomade offering high shine, perfect for a more polished, classic quiff look.

Maintenance Schedule

To keep your quiff looking its best, schedule regular barber visits every 4-6 weeks to maintain the proper length and shape. Between appointments, regular washing and conditioning, along with restyling as needed using preferred products, will keep the quiff in top form.

The quiff is a versatile and stylish old money hairstyle that offers a modern take on classic volume and sophistication.

8. The Crew Cut: Practicality and Clean Lines

Military Crew Cut mens haircutsMilitary Crew Cut mens haircuts

The crew cut is a classic, low-maintenance hairstyle characterized by short hair all around the head, with slightly longer hair on top that gradually tapers down to the sides and back. Its clean, masculine appearance and easy upkeep make it a popular choice for men who value simplicity and practicality without sacrificing style.

The Old Money Connections of the Crew Cut

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

Crew Cut Men HistoryCrew Cut Men History

The crew cut’s association with the old money aesthetic stems from its neat, well-groomed appearance and connection to prestigious universities and military tradition. Its simplicity and practicality align with the understated elegance and academic discipline often associated with old money families. It’s a haircut that speaks of efficiency and quiet confidence.

Ideal Hair Type, Length, and Volume

The crew cut works well with most hair types and textures, from fine to thick, and straight to wavy. Its versatility makes it an accessible style for many.

The ideal length is between 1/2 inch to 1 inch on top, with sides and back gradually tapering down to 1/8 inch or less. Volume is minimal due to the short length, keeping the hair close to the scalp. This low-volume, no-fuss style is perfect for men who prefer a neat, tidy appearance without extensive styling.

Celebrities Known for the Crew Cut

  • Ryan Reynolds: Reynolds often sports a classic crew cut, showcasing its timeless appeal and ability to complement various face shapes, highlighting its universal appeal.

Ryan Reynolds Crew CutRyan Reynolds Crew Cut

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

Tom Hardy Crew CutTom Hardy Crew Cut

  • Channing Tatum: Tatum’s crew cut demonstrates the style’s versatility, effortlessly transitioning from casual settings to more formal occasions, proving its adaptability and timelessness.

Channing Tatum Crew CutChanning Tatum Crew Cut

Styling Guide for the Crew Cut

  1. Apply Matte Product: Start with a small amount of matte pomade or styling cream on clean, damp hair.
  2. Distribute Evenly: Apply from top down, distributing evenly with fingers.
  3. Style Top as Desired: Style the top hair forward, to the side, or in a textured manner using fingers or a comb.
  4. Smooth for Polished Look: For a more polished appearance, brush or comb to smooth the top hair for a uniform finish.
  5. Add Texture if Desired: Apply a small amount of hair wax or clay to the 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 highlights the crew cut’s neat, polished look, while well-groomed stubble or a short beard adds a rugged, masculine touch. A neatly trimmed moustache or goatee can also complement the hairstyle’s simple yet refined nature for a balanced appearance.

Recommended Products

  • American Crew Forming Cream: Provides pliable, low-shine hold to tame and style short hair effectively.
  • Baxter of California Clay Pomade: Offers a matte, textured finish with strong, pliable hold without added shine.

Maintenance Schedule

Regular barber visits every 2-4 weeks are recommended to keep the crew cut sharp and well-maintained, depending on hair growth and desired length. Between appointments, regular washing and minimal product use will suffice for upkeep, reflecting its low-maintenance appeal.

The crew cut is a timeless, low-maintenance old money hairstyle that embodies clean, masculine aesthetics and practical elegance.

9. The Buzz Cut: Minimalist Confidence

Classic Buzz Cut hairstylesClassic Buzz Cut hairstyles

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 typically ranging 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 Unexpected Old Money Connection of the Buzz Cut

While not traditionally considered an old money hairstyle, the buzz cut’s origins in the military and its emphasis on simplicity and practicality align with old money aesthetics. Its minimalist appearance and low-maintenance nature can be seen as a rejection of excess and a focus on functionality, values often associated with old money lifestyles.

Additionally, the buzz cut’s popularity among influential figures across various fields has elevated its status, making it a timeless, classic choice for men from diverse backgrounds. It embodies understated confidence and practicality, aligning with the ethos of quiet wealth.

Ideal Hair Type, Length, and Volume

The buzz cut works well with most hair types and textures, from fine to thick, and straight to curly. Its uniform short length minimizes the appearance of volume and texture differences, making it a versatile choice for various hair types.

The ideal length 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. The buzz cut is inherently low volume, emphasizing its minimalist aesthetic.

Celebrities Known for the Buzz Cut

  • David Beckham: Beckham has sported various buzz cut styles, showcasing its versatility and ability to complement different face shapes and personal styles, proving its adaptability across looks.

David Beckham Buzz CutDavid Beckham Buzz Cut

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

Zayn Malik buzz cutZayn Malik 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, solidifying its association with assertive masculinity.

Styling Guide for the Buzz Cut

  1. Towel or Air Dry: After showering, towel dry or allow hair to air dry.
  2. Optional Matte Product: If desired, apply a small amount of matte pomade or wax for a hint of texture and definition.
  3. Smooth for Polished Look: For a more polished appearance, use a soft-bristled brush to smooth the hair for a neat, uniform finish.

Facial Hair Pairings

The buzz cut’s minimalist, masculine appearance pairs well with various facial hairstyles. A clean-shaven face highlights the cut’s sleek, streamlined look, while well-groomed stubble or a short beard adds a rugged, masculine edge. A neatly trimmed goatee or a short, well-defined beard can also complement the hairstyle’s simple yet confident nature for a balanced and modern appearance.

Recommended Products

  • American Crew Firm Hold Gel: Provides strong, non-flaking hold with low shine, adding control and definition.
  • Baxter of California Grooming Cream: Offers a lightweight, nourishing formula to moisturize the scalp and add a subtle, matte finish, promoting scalp health and subtle style.

Maintenance Schedule

Regular barber visits every 2-3 weeks are recommended to maintain the buzz cut’s neat, uniform appearance, depending on hair growth and desired length. Between appointments, regular washing with gentle shampoo will keep the scalp clean and healthy, ensuring minimal upkeep.

The buzz cut is a minimalist, confident old money hairstyle that embodies simplicity, practicality, and understated masculinity.

10. The Comb Over: Refined and Contemporary

Comb Over Old Money Style HaircutComb 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 evenly tapered or faded. The modern comb over balances traditional elegance with contemporary old money fashion, making it a popular choice for men who want to project a confident image of contemporary sophistication.

The Old Money Heritage 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. Its 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, incorporating modern elements like tapered sides and textured finishes while maintaining its classic roots. This adaptability has allowed it to remain a timeless choice for men who appreciate the old money aesthetic but also want to embrace contemporary styling trends. It’s a style that respects tradition while embracing modernity.

Ideal Hair Type, Length, and Volume

The comb over works best with medium to fine hair with a slight natural wave or straight texture. This hair type provides the necessary manageability and smoothness for the style.

The top hair should be between 2-4 inches long, allowing enough length to create a smooth, swept-over look. Sides and back should be shorter, typically between 0.5-2 inches, depending on desired contrast and personal preference. The comb over’s volume can be customized from sleek and flat to more voluminous and textured, adapting to individual face shapes and style preferences.

Celebrities Known for the Comb Over

  • George Clooney: Clooney’s classic comb over with a side part exemplifies the style’s timeless appeal and its ability to project refined sophistication, demonstrating its enduring elegance across age groups.

George Clooney Classic comb-over HairstyleGeorge Clooney Classic comb-over Hairstyle

  • Ryan Gosling: Gosling’s modern comb over features shorter sides and a textured, volumized top, showcasing the style’s adaptability to contemporary trends, proving its versatility across modern styles.

  • 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, highlighting its adaptable nature.

Leonardo DiCaprio Comb Over HairstyleLeonardo DiCaprio Comb Over Hairstyle

Styling Guide for the Comb Over

  1. Damp Hair and Product Application: Start with clean, damp hair and apply a small amount of styling cream or pomade to the top hair, distributing evenly.
  2. Blow Dry and Sweep: Use a blow dryer and a round brush to sweep the top hair over to one side, creating volume and a smooth, polished finish.
  3. Textured Modern Look Option: For a more textured, modern look, use a matte pomade or clay to add definition and movement.
  4. Create Side Part: Use a fine-toothed comb to create a neat, defined side part.
  5. Finish with Hairspray: 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 highlights the comb over’s neat, refined look, while well-groomed stubble or a short beard adds texture and masculinity. A neatly trimmed goatee or a well-defined moustache can also complement the hairstyle’s blend of classic and modern elements for a balanced, contemporary appearance.

Recommended Products

  • Blind Barber 90 Proof Pomade: Provides strong, pliable hold with moderate shine, ideal for sleek, polished comb overs.
  • Hanz de Fuko Claymation: Offers a matte, textured finish with stronghold, perfect for more modern, volumized comb over styles.

Maintenance Schedule

Regular barber visits every 3-4 weeks are recommended to keep the comb over sharp and well-maintained, trimming sides and back and maintaining top length. Consistent maintenance is key to preserving its refined and contemporary look.

The comb over haircut is ideal for men who want to project confidence and modern sophistication while embracing old money aesthetics infused with contemporary trends.

11. The French Crop: Effortless Style and Texture

French Crop Fringe haircuts for menFrench Crop Fringe haircuts for men

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 Simplicity 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 of understated elegance. The Caesar cut, originating in ancient Rome and popularized by Julius Caesar, has become a timeless, iconic hairstyle known for its clean lines and practicality.

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 but prefer a more relaxed and modern execution.

Ideal Hair Type, Length, and Volume

The French crop works well with most hair types and textures, from fine to thick, and straight to wavy, showcasing its versatility.

The ideal length for the top is 1-2 inches, allowing enough hair to create a textured, slightly messy appearance. Sides and back 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 its effortless and refined appearance.

Celebrities Known for the French Crop

  • Cillian Murphy: Murphy’s French crop in “Peaky Blinders” features a longer, textured top with shaved sides, demonstrating the style’s adaptability to period dramas and modern fashion, blending historical and contemporary styles seamlessly.

Cillian Murphy French Crop haircutCillian Murphy 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, highlighting its versatile masculinity.

  • Daniel Craig: Craig’s interpretation includes a shorter top and faded sides, creating a clean, minimalist look that complements his sharp features, emphasizing its clean and refined simplicity.

Styling Guide for the French Crop

  1. Damp Hair and Texture Spray: Start with clean, damp hair and apply a small amount of sea salt spray or texturizing spray to the top, distributing evenly.
  2. Blow Dry and Tousle: Use a blow dryer on low heat to dry the top hair while using fingers to create a textured, tousled appearance.
  3. Apply Matte Clay: Apply a small amount of matte clay or putty to the top, using fingers to define texture and create a slightly messy, lived-in look.
  4. Comb for Polished Look: For a more polished appearance, use a comb to style the top hair forward or to the side for 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 highlights the crop’s neat, refined appearance, while well-groomed stubble or a short beard adds ruggedness and masculinity. A neatly trimmed goatee or a well-maintained 5 o’clock shadow can also complement the hairstyle’s blend of classic simplicity and modern texture for a balanced, contemporary look.

Recommended Products

  • Baxter of California Clay Pomade: Offers pliable hold with a matte finish, ideal for textured, tousled French crop styles.
  • Triumph & Disaster Karekare Sea Salt Spray: Adds volume and texture, enhancing the French crop’s signature messy, lived-in appearance.

Maintenance Schedule

Regular barber visits every 3-4 weeks are recommended to keep the French crop sharp and well-defined, maintaining top length and neatly trimming sides and back. Consistent maintenance ensures its refined yet effortless style.

The French crop is a versatile old money hairstyle that offers a blend of effortless style, texture, and refined simplicity, perfect for the modern gentleman.

12. The Side Fringe: Youthful and Textured

Side Fringe haircuts for menSide Fringe haircuts for men

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 Modern Old Money Interpretation 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 grooming staple since the 1940s, continually adapted to incorporate modern 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, offering a youthful yet refined option.

Ideal Hair Type, Length, and Volume

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

The ideal length for the top is between 2 and 4 inches, allowing enough hair to create a substantial fringe and enable versatile styling. Sides and back are usually kept shorter, between 1 and 2 inches, and can be textured, tapered, or undercut for a contemporary, edgy look. The side fringe’s volume is typically moderate to high, emphasizing a full, lush fringe that can be styled in various ways, adding to its youthful and dynamic appeal.

Celebrities Known for the Side Fringe

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

Timothée Chalamet Side Fringe HairstyleTimothée Chalamet Side Fringe Hairstyle

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

  • 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, proving its adaptability from casual to polished styles.

Styling Guide for the Side Fringe

  1. Damp Hair and Volumizing Product: Start with clean, damp hair and apply a small amount of volumizing mousse or sea salt spray to the top, distributing evenly.
  2. Blow Dry and Sweep: Use a blow dryer to dry the top hair while using a round brush to sweep the hair to the side and create volume.
  3. Apply Matte Product: Apply a small amount of matte pomade or styling cream to the top, using fingers to define the fringe and create a textured, piece-y appearance.
  4. Tousle for Relaxed Look: For a more relaxed, tousled look, use fingers to gently mess up the fringe and add a carefree, lived-in vibe, enhancing its casual appeal.

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 highlights the side fringe’s soft, textured appearance, keeping the focus on the hair. Light stubble or a short, well-groomed beard can also add a touch of maturity and masculinity without overwhelming the hairstyle’s casual, effortless charm, maintaining a balanced and contemporary appearance.

Recommended Products

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

Maintenance Schedule

Regular barber visits every 4-6 weeks are recommended to keep the side fringe fresh and well-defined, maintaining top length and neatly trimming sides and back. Consistent maintenance ensures its youthful and textured style remains sharp.

The side fringe is a youthful, textured old money hairstyle that combines classic side-swept elements with modern, tousled finishes, offering a relaxed yet refined contemporary option.

13. The Regulation Cut: Military Precision and Order

Regulation Cut MenRegulation Cut Men

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 Values Reflected in 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, viewing it as a rite of passage and a mark of social status.

Regulation Cut Military HistoryRegulation Cut Military History

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, embodying a sense of disciplined elegance.

Ideal Hair Type, Length, and Volume

The regulation cut works well with most hair types and textures, as its short length and high-and-tight style minimize the impact of individual hair characteristics, making it broadly accessible.

The ideal length for the top is between 0.5 and 1 inch, while sides and back are usually buzzed down to a uniform length of 1/8 inch or less, creating a sharp contrast. Due to its extremely short length, the regulation cut has minimal volume and is characterized by a flat, close-to-the-head appearance. This lack of volume contributes to the style’s neat, disciplined look and low-maintenance nature, emphasizing its practical and orderly aesthetic.

Celebrities Known for the Regulation Cut

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

Jake Gyllenhaal Regulation CutJake Gyllenhaal Regulation Cut

  • Tom Hardy: Hardy’s haircut in “Warrior” demonstrates the style’s versatility and potential to complement a muscular, athletic physique, highlighting its adaptability to strong, athletic builds.

  • 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, showcasing its clean and disciplined aesthetic in a civilian context.

Styling Guide for the Regulation Cut

  1. Minimal Styling Needed: Due to the regulation cut’s extremely short length, styling is minimal, primarily focused on maintaining a neat, uniform appearance.
  2. Optional Matte Product: For a polished look, apply a small amount of matte pomade or wax to the top and distribute evenly with fingers for a smoother appearance.

Facial Hair Pairings

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

Recommended Products

  • American Crew Fiber: A matte-finish, high-hold product to add texture and definition to the short top hair.
  • Baxter of California Super Close Shave Formula: A soothing, lubricating shave cream to ensure a smooth, irritation-free shave when maintaining the regulation cut’s clean, close-cropped appearance, essential for scalp and skin health.

Maintenance Schedule

Frequent barber visits every 1-2 weeks are essential to maintain the precise, uniform appearance of the regulation cut, keeping sides and back closely cropped and top trimmed to the desired length. Between visits, regular washing with gentle shampoo and moisturizing conditioner will maintain scalp health and prevent dryness, ensuring consistent cleanliness and comfort.

The regulation cut is a clean, precise old money hairstyle embodying the discipline, order, and efficiency of military tradition, offering a neat, practical, and highly disciplined look.

14. The Short Curtain: Retro Cool with Modern Flair

Short CurtainShort Curtain

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 90s Revival and Old Money Connection 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, becoming a defining style of that era. While not directly associated with old money fashion in its initial run, its revival in recent years reflects a broader nostalgia trend and a renewed appreciation for vintage hairstyles, connecting it to a timeless sense of style.

Leonardo DiCaprio and Johnny Depp Short Curtain Hair 90sLeonardo DiCaprio and Johnny Depp Short Curtain Hair 90s

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, offering a retro yet refined option.

Ideal Hair Type, Length, and Volume

The short curtain hairstyle works best with straight to slightly wavy hair with a medium to fine texture, allowing the hair to fall naturally and create the curtain effect.

The ideal length for the top is between 2 and 4 inches, enough to create the signature curtain-like part and fall naturally. Sides and back are usually kept shorter, between 1 and 2 inches, to emphasize the curtain effect on top. The short curtain’s volume is typically moderate, focusing on a natural, effortless appearance rather than excessive height or fullness, maintaining its relaxed and understated vibe.

Celebrities Known for the Short Curtain

  • Timothée Chalamet: Chalamet’s short curtain hairstyle has become a signature look, showcasing the style’s youthful, carefree charm and ability to complement various fashion choices, solidifying its contemporary relevance.

  • Charles Melton: Melton’s interpretation features a slightly longer top and a more tousled, textured finish, demonstrating the style’s versatility and potential for customization, showcasing its adaptability to different textures and styles.

Charles Melton Short Curtain HairstyleCharles Melton Short Curtain Hairstyle

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

Styling Guide for the Short Curtain

  1. Damp Hair and Moisturizing Cream: Start with clean, damp hair and apply a small amount of lightweight, moisturizing hair cream or serum to the top, distributing evenly.
  2. Create Middle Part: Use a comb to create a middle part, ensuring hair falls naturally to either side.
  3. Air Dry for Natural Look: Allow hair to air dry for a natural, effortless look, or use a blow dryer on low heat to encourage hair to fall in the desired direction.
  4. Refine with Pomade (Optional): 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, maintaining its balance of retro and refined.

Facial Hair Pairings

The short curtain hairstyle’s laid-back, youthful appearance pairs well with clean-shaven faces, keeping the focus on the hair and its unique parted style, enhancing its retro charm. Light stubble or a short, well-groomed beard can also work, adding a touch of maturity and masculinity without overwhelming the hairstyle’s effortless, natural vibe, maintaining a balanced and contemporary look.

Recommended Products

  • Malin + Goetz Sage Styling Cream: A lightweight, moisturizing cream providing soft, natural hold and enhancing hair texture and shine.
  • Aesop Violet Leaf Hair Balm: A nourishing, non-greasy balm to tame frizz, add definition, and protect hair from environmental stressors, promoting hair health and style.

Maintenance Schedule

Regular barber visits every 4-6 weeks are recommended to keep the short curtain fresh and well-maintained, trimming sides and back and keeping top at desired length. Between appointments, gentle, sulfate-free shampoo and conditioner will maintain hair’s natural moisture and prevent damage. Lightweight, non-greasy styling products will enhance natural texture and fall, ensuring effortless style.

The short curtain hairstyle is a retro-inspired old money hairstyle that combines vintage charm with contemporary cool, offering a nostalgic yet stylish option for the modern gentleman.

15. The Edgar Haircut: Edgy Modernity with Precision

15 Old Money Hairstyles Curated for Gents Who Want to Look Rich15 Old Money Hairstyles Curated for Gents Who Want to Look Rich

The Edgar haircut, also known as the “South of France” haircut, is a modern, edgy style that has recently gained 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 Modern Interpretation of Old Money Grooming in 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 modern take on meticulous grooming with a bold, individualistic twist.

Ideal Hair Type, Length, and Volume

The Edgar haircut works best with straight to slightly wavy hair with a medium to thick texture, providing the necessary structure and volume for its distinctive shape.

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. Sides and back are usually faded or undercut, with length gradually decreasing from top to bottom for a sharp, contemporary contrast. The Edgar’s volume is typically high, focusing on creating a bold, attention-grabbing silhouette that emphasizes angular lines and textured finish, making a strong style statement.

Celebrities Known for 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, highlighting its modern and athletic vibe.

Kylian Mbappé Edgar HairstyleKylian Mbappé Edgar Hairstyle

  • Anwar Hadid: Hadid, the model, has been seen with a tousled, textured Edgar cut, demonstrating the style’s edgy, fashion-forward vibe and its adaptability to high-fashion contexts, showcasing its trendy and modern appeal.

Anwar Hadid Edgar HairstyleAnwar Hadid 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, highlighting its capacity for bold and individualistic styling.

Styling Guide for the Edgar Haircut

  1. Damp Hair and High-Hold Product: Start with clean, damp hair and apply a small amount of high-hold styling gel or pomade to the top, distributing evenly.
  2. Style Angular Fringe: Using a comb or fingers, style the top hair forward or upward, creating a sharp, angular fringe just above the eyebrows, defining its signature shape.
  3. Blow Dry for Hold and Shape: Use a blow dryer on high heat to lock the style, directing airflow upward and forward to emphasize angular shape and texture.
  4. Matte Clay for Texture (Optional): 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, adding to its modern and dynamic texture.

Facial Hair Pairings

The Edgar haircut’s bold, contemporary appearance is often paired with clean-shaven faces, keeping focus on the hair’s sharp lines and angular styling, emphasizing its modern and clean aesthetic. For those who prefer facial hair, a well-groomed, shaped beard or goatee can work, adding dimension and personal style while ensuring facial hair complements the haircut’s clean, defined lines, maintaining a balanced and sharp overall look.

Recommended Products

  • Hanz de Fuko Heavymade Pomade: A high-hold, water-based pomade with a strong, long-lasting hold and natural, satin finish, ideal for sharp, angular styles.
  • Layrite Cement Matte Hair Clay: A pliable, matte-finish clay with strong, texturizing hold, perfect for Edgar’s signature disheveled, edgy look.

Maintenance Schedule

Frequent barber visits every 2-3 weeks are essential to maintain the Edgar haircut’s precise, angular appearance, keeping sides and back faded or undercut and top trimmed to the desired length and shape. Lightweight, water-based styling products will restyle hair as needed, ensuring angular fringe and textured finish remain intact, preserving its distinctive and modern style.

The Edgar haircut is a modern, edgy old money hairstyle that offers a bold, contemporary take on precision grooming, perfect for making a stylish statement.

What’s the Right Hairstyle for Me? Tailoring Old Money Haircuts to You

Choosing the ideal old money haircut involves considering several key factors, including your unique facial features, lifestyle, fashion style, and age. Understanding these elements is crucial for selecting a hairstyle that not only embodies the old money aesthetic but also complements your individual attributes.

Old Money style grooming and hairOld Money style grooming and hair

Face Shape: The Foundation of Haircut Selection

Understanding your face shape is paramount in choosing a hairstyle that flatters your features and enhances your overall appearance. Different haircuts can accentuate or soften various facial shapes, creating a more balanced and harmonious look. Utilize a simple and quick online quiz to help determine your face shape for personalized styling.

The primary face shapes include:

Oval Face Shape: Characterized by a length slightly greater than width, a rounded jawline, and a forehead slightly wider than the chin. This versatile face shape is compatible with most hairstyles. Focus on styles that maintain natural balance and proportion, enhancing rather than altering the oval shape.

Round Face Shape: Nearly equal in length and width, with a soft, curved jawline and no prominent angles. Choose hairstyles that add height and volume on top while keeping sides and back short. This elongates the face and introduces more angularity, counteracting the roundness.

Square Face Shape: Defined by a strong, angular jawline and a forehead approximately the same width as the chin. Opt for styles that soften the strong angles of the jawline. Haircuts with shorter sides and a slightly longer, textured top can add softness and balance to the square shape.

Heart Face Shape: Wider at the forehead and cheekbones, narrowing to a pointed chin. Select hairstyles that balance the wider forehead and narrower chin. Side-swept fringes or medium-length tops with shorter sides can add width at the chin and reduce the forehead’s apparent width.

Diamond Face Shape: Widest at the cheekbones, with a narrower forehead, chin, and pointed jawline. Choose styles that add volume and width at the chin and forehead while keeping hair closer to the head at the cheekbones. This minimizes width at the cheekbones and creates a more balanced overall shape.

Hair Type and Texture: Guiding Hairstyle Choices

Your hair type and texture significantly influence which old money hairstyles will work best for you. Different hair types have unique characteristics that can either enhance or complicate certain styles.

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 it easier to achieve sleek, polished looks. Focus on styles that add volume and texture to prevent hair from appearing flat or lifeless.

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

Curly Hair: Forms tight, defined ringlets or coils from scalp to ends. Opt for old money hairstyles that work with natural curl pattern, like the French crop or regulation cut. Use products that provide moisture, definition, and frizz control. Consider using a diffuser when drying to maintain curl integrity.

Kinky/Coily Hair: Characterized by very tight, densely packed curls or coils, often with a zig-zag or Z-shaped pattern. Select hairstyles that embrace natural texture, such as the buzz cut or a short, tapered afro. Use moisturizing, nourishing products to keep hair healthy and defined. Protective styling techniques can minimize damage and maintain natural pattern.

Lifestyle and Maintenance: Practical Considerations

When choosing an old money hairstyle, consider your lifestyle and the level of maintenance you are 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 preference for low-key grooming, opt for low-maintenance old money hairstyles such as:

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

These styles typically require less frequent barber visits and minimal product, ideal for those who value simplicity and efficiency in their grooming routine.

For those who enjoy dedicating time to grooming and appreciate styling, consider old money hairstyles that offer more 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 for various occasions and personal preferences, offering more versatility and stylistic range.

Old Money Hairstyles by Age Groups: Tailoring to Different Life Stages

While old money hairstyles are timeless and suitable for men of all ages, certain styles may be perceived as more appropriate for specific age groups. Adjusting your hairstyle accordingly can enhance your overall appearance and reflect your current life stage.

Younger Men (18-30): Younger men have the most flexibility in experimenting with old money hairstyles, often able to pull off bolder, more contemporary looks without appearing out of place. Styles that work particularly well 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 individuality while adhering to old money aesthetic principles.

Middle-Aged Men (31-50): For middle-aged men, the focus should be on selecting old money hairstyles that convey maturity, refinement, and established success. Suitable styles 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 age-appropriate, flattering, and easy-to-maintain old money hairstyles. Styles that work particularly well 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 natural changes in hair texture and density often associated with aging, while still projecting refinement and sophistication.

Final Thoughts: Embracing Timeless Elegance

The old money aesthetic, deeply rooted in traditional values and understated wealth, offers a confident and enduring style. In a world dominated by fleeting trends and overt displays of new money, the old money aesthetic stands as a beacon of steadfast refinement, conveying excellence and self-assurance through subtle elegance.

An old money haircut is central to achieving this distinguished look, representing the quickest and most cost-effective way to project timeless elegance, refined sophistication, and a rich heritage. It’s more than just a haircut; it’s a statement of enduring style and quiet confidence.

The key to selecting the right old money haircut lies in considering your individual features, lifestyle, and personal preferences. Choose a style that makes you feel confident, comfortable, and authentically yourself. By taking the time to understand these factors and experiment with different options, you can discover the perfect old money haircut 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

To truly embody the old money aesthetic, remember that styling goes beyond just the haircut. Professional styling, as understood by expert image consultants, begins with knowing your unique body shape and seasonal color palette. These are paramount factors in choosing clothes that fit perfectly and feature colors that complement your skin, eyes, and hair, forming the foundation of a sophisticated and harmonious look.

Only then can a stylist effectively engage in styling by occasion, location, season, and time of day. This involves selecting garments, footwear, and accessories from stylistically relevant heritage fashion brands to project high confidence and success. It’s about creating a cohesive and polished image that speaks volumes without uttering a word.

The best part? You can begin this journey yourself. Discover your body shape, seasonal color palette, and ideal fashion style in less than 5 minutes with these simple steps:

1. Find Your Body Shape: Different garments flatter different silhouettes. Knowing your body shape is the first step to dressing confidently. Take a free body shape quiz for men to identify your unique shape and understand how to best dress for it.

2. Find Your Unique Color Palette: Ensure that every color in your wardrobe complements your natural coloring. Take a free seasonal color quiz for men to discover your seasonal color palette and learn which hues enhance your natural features.

3. Find Your Ideal Fashion Style: By now, you should know your body shape and color palette. The next step is to discover your ideal personal fashion style. Take a free fashion style quiz for men to reveal your ideal style, outfit ideas, relevant fashion brands, and much more, guiding you towards a cohesive and authentic personal brand.

4. Professional Image Consultancy with The VOU: For those seeking to refine their style to a professional level, consider expert image consultants and fashion stylists. Professional styling services for men offer comprehensive and detailed guidance, backed by leading stylists who will help you create looks that communicate affluence, elegance, and success.

Remember, wearing luxury brands alone is insufficient. True style, confidence, and success in appearance require a foundational understanding of your body shape, color palette, and personal style. Only then can you effectively style yourself by occasion, location, season, and time of day, creating a consistently impressive and appropriate image.

Contact expert stylists today to save time, money, and potential styling missteps. It’s time to dress like a confident, successful gentleman with exquisite fashion taste—begin with a free styling assessment.

By 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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