15 Most Popular Old Money Hairstyles for Modern Gentlemen

The old money aesthetic, associated with the upper echelons of society, displays a confident look built on traditional values and silent wealth.

An old-money hairstyle is central to achieving this distinguished look and the fastest and cheapest way to create an image of timeless elegance, refined sophistication, and a rich heritage.

In a world of fast fashion trends and new money statements, the old-money aesthetic remains a bastion of steadfast refinement that conveys excellence and self-assurance.

Choosing the right hairstyle requires considering factors such as face shape, hair texture, volume, facial hair, and even body shape and desired fashion style to create a cohesive appearance.

From the classic side part to the understated Ivy League, this article explores the various hairstyles that epitomise the old-money aesthetic and offers guidance on selecting the right hairstyle for your features and lifestyle.

1. The Classic Side Part

The classic side part is a timeless hairstyle for men characterised by a sharp, defined part that divides the hair laterally, usually from the crown to the temple.

The hair on the top is kept slightly longer than the sides, which are tapered or faded for a clean look.

Why this is an Old Money Style

The Classic Side Part emerged in the 1920s and 1930s, popularised by Hollywood icons like Cary Grant and Fred Astaire, as a departure from the longer, slicked-back looks of earlier decades and became a symbol of refined masculinity.

With clean lines and a structured appearance, the Classic Side Part coveys a sense of order and discipline, key values in the old-money aesthetic.

Ideal Hair Texture, Length, and Volume

The Classic Side Part works best with medium to fine hair with a slight natural wave.

The hair on the top should be long enough to comb over and maintain the part, normally around 2-4 inches.

The sides are kept shorter, usually between 0.5 and 1 inch. Aim for a balanced volume that maintains the style’s structure without appearing too stiff or heavy.

Celebrity and Style Icons

• Jon Hamm, in his role as Don Draper in “Mad Men,” Hamm’s Classic Side Part has become a modern style reference.

• George Clooney’s side part silver fox hair is a famous example of the classic side part old money hairstyle

• David Beckham – the soccer icon has sported various iterations of the Classic Side Part hairstyle, demonstrating the cut’s enduring appeal.

• Ryan Gosling’s take on the side part features a slightly longer top and a more relaxed, textured finish.

Styling Techniques

• Start with damp, towel-dried hair and apply a small amount of pomade or styling cream, focusing on the roots and working to the ends.
• Use a fine-toothed comb to create a clean, defined part, starting from the crown and working towards the temple.
• Blow-dry the hair on the top toward the part, using a round brush to add volume and smoothness.
• For a relaxed look, use your fingers to gently tousle the hair on the top, maintaining the part’s structure.

Facial Hairstyle Options

The Classic Side Part pairs well with a clean-shaven face, emphasising the hairstyle’s sharp, polished appearance.

However, a well-groomed moustache or a neatly trimmed beard can also complement the look, adding a touch of vintage charm or modern sophistication.

Recommended Hair Products

A high-quality pomade or styling cream with a medium to strong hold and a slight sheen, such as Baxter of California’s Hard Water Pomade or Creed’s Green Irish Tweed Hair Pomade.

A lightweight hair spray for added hold and frizz control, like R+Co’s Outer Space Flexible Hairspray.

Maintenance and Barber Visits

To maintain the Classic Side Part’s sharp appearance, regular trims every 3-4 weeks are essential.

Ensure that your barber understands the style you’re aiming for and can tailor the cut to your hair type and face shape.

Between visits, touch up the part daily and restyle as needed.

The Classic Side Part remains a cornerstone of old-money hairstyles, offering a timeless and adaptable look that suits a wide range of face shapes and personal styles.

2. The Slick Back

The Slick Back is a timeless hairstyle oozing tasteful refinement achieved by brushing the hair back and away from the face, creating a smooth, polished appearance.

 Why this is an Old Money Style

The Slick Back hairstyle rose to prominence in the 1920s and 1930s, during the Golden Age of Hollywood.

Stars like Clark Gable and Humphrey Bogart popularised the look, which became synonymous with the suave gentleman.

The Slick Back’s association with the old-money aesthetic lies in its ability to convey confidence, refinement, and a sense of effortless style.

Ideal Hair Texture, Length, and Volume

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

The hair should be long enough to comb back and maintain the style, typically around 3-5 inches on the top and 1-2 inches on the sides and back.

Aim for a balanced volume that creates a smooth, sleek appearance without looking too flat or lifeless.

Celebrity and Style Icons

• Leonardo DiCaprio’s Slick Back in “The Great Gatsby” captured the style’s old-money charm and sophistication to perfection.

• Michael Douglas’s portrayal of Gordon Gekko in “Wall Street” featured a classic Slick Back, cementing the style’s association with power and success.

• Jake Gyllenhaal’s red-carpet appearances feature a modern take on the Slick Back, with a slightly textured finish and less severe hold.

Styling Techniques

• Start with damp, towel-dried hair and apply a small amount of pomade or hair gel, focusing on the roots and working through to the ends.
• Use a wide-toothed comb to slick the hair back, starting from the forehead and working towards the crown.
• For a glossy look, use a fine-toothed comb to create a smooth, even finish.
• 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 Hairstyle Options

The Slick Back pairs well with a clean-shaven face, emphasising the hairstyle’s polished and sophisticated appearance.

However, a well-groomed beard or moustache can add a touch of masculinity and create a more modern, edgy look.

Recommended Hair Products

A high-quality pomade with a strong hold and high shine, such as Layrite’s Super Hold Pomade or Suavecito’s Firme Hold Pomade.

A medium-hold hair gel for a sleeker, wet-look finish, like American Crew’s Firm Hold Styling Gel.

Maintenance and Barber Visits

Regular trims are recommended every 4-6 weeks to maintain the Slick Back’s polished appearance.

Ensure that 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 the 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

The Ivy League hairstyle is a classic, Preppy look that depicts refined scholarly elegance.

It is a timeless haircut featuring a short, neat appearance with a slight quiff at the front, precisely tapered sides, and a crisp side part.

 Why this is an Old Money Look

Drawing its name from the esteemed Ivy League universities in the United States, such as Harvard, Yale, and Princeton, the Ivy League style emerged in the 1920s and gained popularity among the young, affluent gentlemen who attended these prestigious institutions.

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

Ideal Hair Texture, Length, and Volume

Fine to medium hair with a slight natural wave is best for a flawless Ivy League haircut.

The texture allows for a neat, structured appearance while maintaining a touch of natural movement.

The hair on the top should be kept relatively short, with just enough length to create a small, subtle quiff at the front.

Aim for a top length of around 1-2 inches, providing sufficient volume and height without appearing overly dramatic.

The sides and back should be tapered shorter, gradually fading from around 1 inch at the top to approximately 0.5 inches near the ears and neckline.

The precise tapering creates a clean, polished look, reinforcing the hairstyle’s crisp lines and refined silhouette found in wealthy people’s hairstyles.

Celebrity and Style Icons

• The 35th President of the United States, John F. Kennedy’s iconic Ivy League haircut epitomised the style’s association with elite education, political power, and timeless sophistication.

• Hollywood heartthrob Ryan Gosling has often sported a modern interpretation of the Ivy League haircut, showcasing the style’s versatility and enduring appeal.

• Silver screen legend Cary Grant’s impeccably styled Ivy League haircut in films like “North by Northwest” and “To Catch a Thief” helped to popularise the style and cement its place in the pantheon of old-money fashion.

Styling Techniques

• On a 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.
• Using a fine-toothed comb, create a crisp side part, starting from the crown and working towards the temple.
• With a blow dryer set to medium heat and medium speed, dry the hair on the top of your head, using a small round brush to create volume and a slight quiff at the front.
• Once the hair on the top is dry and styled, use your fingers or a comb to refine the quiff gently, ensuring a neat, structured finish.

Facial Hairstyle Options

The Ivy League haircut is best complemented by a clean-shaven face, emphasising the style’s neat, polished appearance and drawing attention to the hair’s 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 the pyramidal, can enhance the Ivy League’s old-money aesthetic and provide a subtle nod to the style icons of a bygone era.

Recommended Hair Products

Baxter of California Clay Pomade – a water-based pomade for a medium hold and a matte finish, making it ideal for creating the Ivy League’s structured yet natural-looking style.

With a light to medium hold and a low-shine finish, American Crew’s Forming Cream is perfect for achieving the Ivy League’s polished yet understated appearance.

To keep your Ivy League haircut in place and protect against humidity and frizz, a lightweight hair spray like Oribe’s Superfine Hair Spray is a must-have.

Maintenance and Barber Visits

Maintaining the Ivy League haircut’s clean, structured appearance requires regular trims every 3-4 weeks.

This frequency ensures that the hair on the 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. The Taper Fade

The taper fade is a contemporary hairstyle that blends the classic elegance of old-money aesthetics with fresh, clean cuts appealing to today’s discerning gentlemen.

The 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.

Why this is an Old Money Haircut

While the taper fade has gained prominence in recent years, its roots can be traced back to the classic, clean-cut hairstyles favoured by the wealthy and influential throughout the 20th century.

Gaining popularity in the 40s, the taper fade’s emphasis on neatness, structure, and precision echoes the timeless values of the old-money aesthetic.

At the same time, its modern interpretation allows for greater flexibility and personal expression.

The taper fade is a great mix of traditional and contemporary styling and is the go-to choice for gentlemen seeking to project elegance in professional and social settings.

Ideal Hair Texture, Length, and Volume

The taper fade is a remarkably versatile hairstyle that can be adapted to suit a wide range of hair types, textures, and lengths.

However, to achieve the most polished and refined results, it is best to start with hair that has a medium to fine texture and a moderate amount of natural volume.

The ideal length for the top portion of the hair will depend on your personal preferences and styling goals, but a 1-4 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.

Celebrity and Style Icons

• Justin 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.

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

• Michael B. Jordan’s taper fades and precise, graduated cuts feature crisp lines and sharp fades that highlight his chiselled features, while the longer lengths on top allow for a range of stylish, textured looks that project an image of confidence and adaptability.

Styling Techniques

• Start with clean, towel-dried hair washed with high-quality shampoo and conditioner and apply a small amount of styling product, such as a pomade, clay, or cream, to the hair on top, working it through from roots to ends with your fingers or a comb.
• Using a blow dryer set to medium heat and medium speed, 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 a texture spray, to the hair on top.

Facial Hairstyle Options

The taper fade’s versatility extends to its compatibility with various facial hairstyles, allowing gentlemen to customise their looks to suit their personal preferences and face shapes.

A clean-shaven face is ideal for a clean cut, which creates a refined appearance that emphasises the taper fade’s structured silhouette.

Alternatively, a well-groomed moustache, carefully trimmed, shaped beard, or precisely styled moustache can enhance the taper fade’s old-money aesthetic while allowing for a greater degree of personal expression and individuality.

Recommended Hair Products

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

Hanz de Fuko Claymation is 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’s Clay Effect Style Spray is excellent when a lightweight, texturising finish is desired.

Maintenance and Barber Visits

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

5. The Undercut

The undercut is a striking, modern hairstyle that combines the refined appeal of old-money aesthetics with a contemporary, daring twist.

The attention-grabbing look features short, buzzed sides and back, contrasting sharply 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.

Why this is an Old Money Style

The undercut originated in the early 20th century and was popular among working-class men and military personnel.

It has recently experienced a resurgence, becoming a favourite among fashion-forward gentlemen who appreciate its blend of classic refinement and rebellious attitude.

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

Ideal Hair Texture, Length, and Volume

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.

The ideal length for the top portion is 2-5 inches, allowing for various styling options and dramatic volume.

The sides and back are usually clipped very short, with a #1 or #2 guard, or even fully buzzed.

The sharp distinction between the top and sides creates a bold, eye-catching silhouette.

Celebrity and Style Icons

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

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

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

Styling Techniques

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

Facial Hairstyle Options

The undercut’s edgy, masculine appeal makes it an ideal companion for various facial hairstyles. A well-groomed beard can add texture and visual interest, while a clean-shaven face highlights the undercut’s sharp lines and bold contrast.

Consider pairing your undercut with neatly trimmed stubble or a short, well-defined beard for a balanced, rugged, yet refined look.

Recommended Hair Products

Layrite Cement Clay provides a firm, pliable hold with a natural, matte finish.

For a classic, slick look with high shine, Suavecito’s oil-based pomade offers superior hold and long-lasting control.

Kevin Murphy Rough Rider clay provides a stronghold and a matte finish for various textures and styles.

Maintenance and Barber Visits

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

6. The Classic Pompadour

The classic pompadour is a timeless hairstyle that exudes old-school sophistication and vintage charm.

The iconic look features hair swept upward and back, creating an 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.

Why this is an Old Money Cut

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

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

Ideal Hair Texture, Length, and Volume

Medium to thick hair with a slight natural wave is ideal for a classic pompadour. The hair should be long enough on top to create the signature swept-up look, typically 3-5 inches.

The sides and back are kept shorter, usually tapered or faded, to emphasise 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.

Celebrity and Style Icons

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

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

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

Styling Techniques

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

Facial Hairstyle Options

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 Hair 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’s Hard Cream Pomade is an excellent choice for a more natural, pliable hold with a subtle sheen.

Suavecito Firme Hold Pomade offers a strong, long-lasting hold with a high-shine finish, perfect for a traditional, slick pompadour.

Maintenance and Barber Visits

Regular barber visits every 3-4 weeks are crucial to maintaining the pompadour’s precise shape and neatly trimming the sides and back.

Daily styling with the appropriate products is necessary to ensure the pomp retains its volume and structure.

7. The Quiff

The quiff is a modern hairstyle combining classic pompadour elements and the 1950s-inspired slick back.

The 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 and the relaxed, textured appeal of modern styling.

Why this is an Old Money Haircut

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

Popularised 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.

The quiff’s adaptability allows it to be styled more relaxed and tousled, reflecting the modern trend towards less structured, more natural-looking hair.

This flexibility makes the quiff an ideal choice for gentlemen who want to incorporate elements of old-money sophistication into a contemporary, easy-to-manage style.

Ideal Hair Texture, Length, and Volume

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

The ideal length for the top portion is 2-4 inches, allowing for enough volume and height to create the signature quiff shape.

The sides and back should be shorter, usually between 0.5 and 2 inches, depending on the desired contrast level and personal preference.

The quiff’s volume can be customised to suit individual tastes, from a more understated, textured look to a bold, sky-high statement.

Celebrity and Style Icons

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

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

• David Gandy’s classic quiff with a side part demonstrates the style’s versatility and ability to bridge the gap between traditional and modern aesthetics.

Styling Techniques

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

Facial Hairstyle Options

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 a well-groomed stubble or 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 Hair 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 and Barber Visits

To keep your quiff looking its best, schedule regular barber visits every 4-6 weeks to maintain the proper length and shape.

Between appointments, wash and condition your hair regularly and restyle it as needed using your preferred products.

8. The Crew Cut

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.

 Why this is an Old Money Style

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.

The crew cut’s association with the old-money aesthetic lies in its neat, well-groomed appearance and connection to prestigious universities and military tradition.

The style’s simplicity and practicality align with the understated elegance and academic discipline associated with old-money families.

Ideal Hair Texture, Length, and Volume

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.

Celebrity and Style Icons

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

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

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

Styling Techniques

• Start with a small amount of matte pomade or styling cream on clean, damp hair, and apply from the top down, distributing it evenly with your fingers.
• Using a comb or your fingers, style the hair on top forward, to the side, or in a slightly messy, textured manner, depending on your desired look.
• For a more polished appearance, brush or comb to smooth the hair on top and create a neat, uniform finish.
• If desired, apply a small amount of hair wax or clay to the hair on top for added texture and definition.

Facial Hairstyle Options

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 a well-groomed stubble or 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 Hair Products

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

American Crew Forming Cream provides a pliable, low-shine hold that helps to tame and style short hair.

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

Maintenance and Barber Visits

To keep your crew cut looking sharp and well-maintained, schedule regular barber visits every 2-4 weeks, depending on your hair growth and desired length.

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

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

The simplicity and practicality of this look make it a go-to choice for men who value a neat, polished appearance without needing extensive styling or upkeep.

9. The Buzz Cut

The buzz cut is a minimalist, low-maintenance hairstyle that exudes confidence and masculinity.

The 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.

Why this is an Old Money Style

While the buzz cut is not a traditional old-money hairstyle, its origins in the military and emphasis on simplicity and practicality align with old-money aesthetics.

The buzz cut’s minimalist appearance and low-maintenance nature can be seen as a rejection of excess and a focus on functionality, 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.

Ideal Hair Texture, Length, and Volume

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 minimises 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.

Celebrity and Style Icons

• David 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.

• Zayn 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.

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

Styling Techniques

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

Facial Hairstyle Options

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 a well-groomed stubble or 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 Hair Products

Due to the buzz cut’s short length, minimal product is needed to maintain the style.

However, the following products can help to keep your hair looking healthy and add a touch of texture or definition:

American Crew Firm Hold Gel provides a strong, non-flaking hold with a low shine, perfect for adding a bit of control and definition to your buzz cut.

Baxter of California Grooming Cream offers a lightweight, nourishing formula that moisturises the scalp and adds a subtle, matte finish to the hair.

Maintenance and Barber Visits

To maintain the buzz cut’s neat, uniform appearance, schedule regular barber visits every 2-3 weeks, depending on your hair growth and desired length.

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

The buzz cut is a minimalist, confident hairstyle that embodies simplicity and practicality.

The fuss-free nature and masculine appearance make this cut ideal for men who value a no-nonsense approach to grooming while still maintaining a stylish look.

10. The Comb Over

The comb-over is a refined hairstyle that has evolved from its traditional roots to become a modern, stylish choice for men.

The look has 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.

Why this is an Old Money Haircut

The comb-over has a rich history that dates back to the early 20th century when it was a popular choice among wealthy and influential men.

The style’s association with old-money fashion lies in its neat, polished appearance and ability to convey sophistication and refinement.

Over the decades, the comb-over has evolved to incorporate modern elements, such as tapered sides and textured finishes, while maintaining its classic roots.

This adaptability has allowed the comb-over to remain a timeless choice for men who appreciate the old-money aesthetic but also want to embrace contemporary styling trends.

Ideal Hair Texture, Length, and Volume

The comb-over works best with medium to fine hair with a slight natural wave or straight texture.

The ideal length for the hair on top is between 2-4 inches, allowing for enough length to create a smooth, swept-over look.

The sides and back should be kept shorter, usually between 0.5-2 inches, depending on the desired contrast level and personal preference.

The comb-over’s volume can be customised to suit your unique face shape, from a sleek, flat look to a more voluminous, textured style.

Celebrity and Style Icons

• George 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.

• Ryan Gosling’s modern comb-over features a shorter length on the sides and a textured, volumised top, showcasing the style’s adaptability to contemporary trends.
• Leonardo 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.

Styling Techniques

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

Facial Hairstyle Options

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 a well-groomed stubble or 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 Hair 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, volumised comb-over styles.

Maintenance and Barber Visits

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

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

11. The French Crop

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.

 Why this is an Old Money Style

While the French crop may not have a direct association with old-money fashion, its roots in the classic Caesar cut and emphasis on simplicity align with old-money values.

The Caesar cut, which originated in ancient Rome, was popularised by the Roman emperor Julius Caesar and has since become a timeless, iconic hairstyle.

The French crop’s modern interpretation of this classic look, with its textured top and clean, tapered sides, reflects a balance between traditional style and contemporary preferences.

This fusion of old and new makes the French crop appealing to men who appreciate the elegance and refinement of old-money aesthetics.

Ideal Hair Texture, Length, and Volume

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

The ideal length for the top is 1-2 inches, which allows enough hair to create a textured, slightly messy appearance.

The back and sides are usually kept shorter, between 0.5 and 1 inch, and can be tapered or faded for a clean, modern look.

The French crop’s volume is typically moderate, focusing on texture rather than height.

Celebrity and Style Icons

• Cillian 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.

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

Styling Techniques

• Start with clean, damp hair and apply a small amount of sea salt spray or texturising spray to the hair on top, distributing it evenly with your fingers.
• Use a blow dryer on a low heat setting to dry the hair on top while simultaneously using your fingers to create a textured, tousled appearance.
• Apply a small amount of matte clay or putty to the hair on top, using your fingers to define the texture and create a slightly messy, lived-in look.
• For a more polished appearance, use a comb to style the hair on top forward or to the side, creating a neat, uniform finish.

Facial Hairstyle Options

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 a well-groomed stubble or short beard can add a touch of ruggedness and masculinity.

For a balanced, contemporary look, consider pairing your French crop with a neatly trimmed goatee or a well-maintained 5 o’clock shadow, which can complement the hairstyle’s blend of classic simplicity and modern texture.

Recommended Hair Products

To achieve and maintain the perfect French crop, invest in products that enhance texture and provide a matte, natural finish:

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

Triumph & Disaster Karekare Sea Salt Spray adds volume and texture to the hair, making it easier to achieve the French crop’s signature messy, lived-in appearance.

Maintenance and Barber Visits

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

12. The Side Fringe

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.

Why this is an Old Money Style

While the side fringe may not be directly associated with old-money fashion, its roots in the classic side-swept look and its emphasis on texture and movement align with the evolution of men’s hairstyles throughout the 20th century.

The side-swept style has been a staple of men’s grooming since the 1940s and has been adapted to incorporate modern elements and trends.

The side fringe’s contemporary interpretation of this timeless look, with its tousled texture and softer, more natural appearance, reflects a shift in men’s grooming preferences towards styles prioritising ease, individuality, and self-expression.

While not strictly adhering to old-money aesthetics, the side fringe represents a continuation of the classic side-swept tradition, updated for the modern age.

Ideal Hair Texture, Length, and Volume

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, emphasising the creation of a full, lush fringe that can be styled in various ways.

Celebrity and Style Icons

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

• Harry Styles’ iconic side fringe features a longer, tousled top and textured sides, epitomising the style’s youthful, carefree charm.
• Cole Sprouse’s side fringe with a shorter length and a more polished finish demonstrates the style’s versatility and potential for a neater, more refined appearance.

Styling Techniques

• Start with clean, damp hair and apply a small amount of volumising 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 simultaneously 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 Hairstyle Options

The side fringe’s youthful, laid-back appearance pairs well with various facial hairstyles, particularly those emphasising 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 a light stubble or a short, well-groomed beard, which can add a touch of maturity and masculinity without overwhelming the hairstyle’s casual, effortless charm.

Recommended Hair 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 and Barber Visits

To keep your side fringe looking fresh and well-defined, schedule regular barber visits every 4-6 weeks to maintain the proper length on top and neatly trim the sides and back.

The side fringe is a youthful, textured hairstyle that combines elements of the classic side-swept look with modern, tousled finishes.

Its laid-back, casual vibe and ability to soften facial features make it an appealing choice for younger men who want to embrace a more relaxed, contemporary aesthetic while still nodding to the timeless tradition of the side-swept style.

13. The Regulation Cut

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.

Why this is an Old Money Style

While the regulation cut may not be directly associated with old-money fashion, its roots in military tradition and emphasis on discipline, order, and cleanliness align with certain old-money values.

The military has long been associated with the upper echelons of society, with many wealthy and influential families sending their sons to serve in the armed forces as a rite of passage and a mark of social status.

The regulation cut’s adherence to strict grooming standards and projection of a neat, put-together appearance reflects the importance placed on self-discipline and presentability within old-money circles.

By embracing the regulation cut, men can tap into this tradition of military precision and the associated values of order, efficiency, and respectability.

Ideal Hair Texture, Length, and Volume

The regulation cut works well with most hair types and textures, as the short length and high-and-tight style minimise 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 characterised by a flat, close-to-the-head appearance.

The lack of volume contributes to the style’s neat, disciplined look and low-maintenance nature.

Celebrity and Style Icons

• Jake 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.

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

Styling Techniques

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

Facial Hairstyle Options

The regulation cut’s clean, disciplined appearance is best complemented by a clean-shaven face, reinforcing the style’s association with military precision and adherence to strict grooming standards.

However, for those who prefer facial hair, a well-maintained, short stubble can work with the regulation cut, provided that it is kept neat and tidy to avoid detracting from the hairstyle’s sharp, put-together look.

Recommended Hair Products

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

However, the following products can help to keep the hair looking clean, healthy, and well-groomed:

American Crew Fiber is a matte-finish, high-hold product that can help to add texture and definition to the short hair on top.

Baxter of California Super Close Shave Formula is a soothing, lubricating shave cream that can help to ensure a smooth, irritation-free shave when maintaining the regulation cut’s clean, close-cropped appearance.

Maintenance and Barber Visits

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

Between visits, wash the hair regularly with a gentle shampoo to keep the scalp clean and healthy, and use a moisturising conditioner to prevent dryness and irritation.

The regulation cut is a clean, precise hairstyle embodying the discipline, order, and efficiency of military tradition.

The sharp, put-together appearance and low-maintenance nature make it an appealing choice for men who value neatness, practicality, and adherence to grooming standards.

14. The Short Curtain

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.

Why this is an Old Money Style

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

The look is not directly associated with old-money fashion. Still, the short curtain’s revival in recent years reflects a broader nostalgia trend and a renewed appreciation for vintage hairstyles.

The short curtain’s blend of classic and contemporary features, low-maintenance nature, and effortless cool factor align with the old-money aesthetic’s emphasis on timeless style, understated elegance, and a certain nonchalance.

Ideal Hair Texture, Length, and Volume

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 emphasise 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.

Celebrity and Style Icons

• Timothée 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’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 customisation.

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

Styling Techniques

• Start with clean, damp hair and apply a small amount of lightweight, moisturising hair cream or serum to the hair on top, distributing it evenly with your fingers.
• Using a comb, create a middle part, ensuring that the hair falls naturally to either side of the part.
• Allow the hair to air dry for a natural, effortless look, or use a blow dryer in a low heat setting to encourage the hair to fall in the desired direction.
• For a more polished appearance, use a small amount of pomade or wax to define the part and add shine, taking care not to disrupt the hair’s natural fall.

Facial Hairstyle Options

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, a light stubble or a short, well-groomed beard can work with the short curtain, adding a touch of maturity and masculinity to the overall look.

The key is to keep the facial hair neat and trimmed to avoid overwhelming the hairstyle’s effortless, natural vibe.

Recommended Hair Products

To achieve and maintain the perfect short curtain hairstyle, consider using the following products:

Malin + Goetz Sage Styling Cream is a lightweight, moisturising cream that provides a soft, natural hold and enhances the hair’s texture and shine.

Aesop Violet Leaf Hair Balm is a nourishing, non-greasy balm that helps to tame frizz, add definition, and protect the hair from environmental stressors.

Maintenance and Barber Visits

To keep your short curtain hairstyle fresh and well-maintained, schedule regular barber visits every 4-6 weeks to trim the sides and back and keep the top at the desired length.

Between appointments, wash your hair with a gentle, sulfate-free shampoo and conditioner to maintain the hair’s natural moisture and prevent damage.

Style as needed using lightweight, non-greasy products that enhance the hair’s natural texture and fall.

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

15. The Edgar

The Edgar haircut, also known as the “South of France” haircut, is a modern, edgy style recently gaining popularity among young men.

The haircut is characterised by its short, often faded sides and back and a longer, textured top typically styled forward or upward to create a sharp, angular fringe.

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.

 Why this is an Old Money Style

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, Edgar’s emphasis on precision cutting, clean lines, and bold styling can be seen as a contemporary interpretation of the attention to detail and grooming standards valued in old money circles.

Edgar-style haircuts allow men to demonstrate self-expression and a willingness to take risks, qualities always admired in fashion-forward individuals, regardless of background.

Ideal Hair Texture, Length, and Volume

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 emphasises the angular lines and textured finish of the hair on top.

Celebrity and Style Icons

• Kylian 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.

• Anwar 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.

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

Styling Techniques

• Start with clean, damp hair and apply a small amount of high-hold styling gel or pomade to the hair on top, distributing it evenly with your fingers.
• Using a comb or your fingers, style the hair on top forward or upward, creating a sharp, angular fringe that falls just above the eyebrows.
• Use a blow dryer on high heat to lock the style in place, directing the airflow upward and forward to emphasise the angular shape and texture of the fringe.
• For a more voluminous, textured look, use a small amount of matte clay or putty to define individual strands and create a slightly messy, edgy finish.

Facial Hairstyle Options

The Edgar haircut’s bold, contemporary appearance is often paired with clean-shaven faces, which helps to maintain the focus on the hair’s sharp lines and angular styling.

However, for those who prefer facial hair, a well-groomed, shaped beard or goatee can work with the Edgar cut, adding an extra layer of dimension and personal style to the overall look.

The key is to ensure that the facial hair is precisely trimmed and complements the clean, defined lines of the haircut.

Recommended Hair Products

To achieve and maintain the perfect Edgar haircut, consider using the following products:

Hanz de Fuko Heavymade Pomade is a high-hold, water-based pomade with a strong, long-lasting hold and a natural, satin finish, ideal for creating sharp, angular styles.

Layrite Cement Matte Hair Clay is a pliable, matte-finish clay with a strong, texturising hold. It is perfect for achieving Edgar’s signature dishevelled, edgy look.

Maintenance and Barber Visits

Frequent barber visits are essential to maintain the Edgar haircut’s precise, angular appearance.

Schedule appointments every 2-3 weeks to keep the sides and back faded or undercut and the top trimmed to the desired length and shape.

Use lightweight, water-based styling products to restyle the hair as needed, ensuring that the angular fringe and textured finish remain intact.

What’s the Right Hairstyle for Me?

Choosing the perfect old-money hairstyle for you involves several key factors, such as your unique facial features, lifestyle, fashion style, and more.

This section will explore these factors in detail and match hairstyles to various face shapes and age groups.

Face Shape

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

Characterised 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 minimise width.

Hair Type and Texture

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

Straight

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

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, moisturising products to define and control the waves without weighing them down.

Curly

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

Characterised 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 moisturising, nourishing products to keep the hair healthy and defined, and consider protective styling techniques to minimise damage and maintain the hair’s natural pattern.

Lifestyle and Maintenance

When choosing an old-money hairstyle, consider your lifestyle and the level of maintenance you’re willing to commit to.

Some styles require frequent trims, daily styling, and specific products, while others are more low-maintenance and easily managed with minimal effort.

If you have a busy lifestyle or prefer a more low-key approach to grooming, opt for old-money hairstyles that are simple, versatile, and easy to maintain, such as:

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

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

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

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

These styles often require more frequent trims, daily styling with specific products, and more time and effort to achieve the desired look.

However, they also allow for greater self-expression and can be adapted to suit various occasions and personal preferences.

Old-Money Hairstyles by Age Groups

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

Younger Men (18-30)

Younger men have the most flexibility when experimenting with old-money hairstyles, as they can often pull off bolder, more contemporary looks without appearing out of place.

Some styles that work particularly well for this age group include:

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

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

Middle-Aged Men (31-50)

For middle-aged men, the focus should be on selecting old-money hairstyles that convey maturity, refinement, and a sense of established success.

Some styles that work well for this age group include:

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

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

Older Men (51+)

For older men, the key is to choose old-money hairstyles that are age-appropriate, flattering, and easy to maintain.

Some styles that work particularly well for this age group include:

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

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

Ultimately, the key to choosing the right old-money hairstyle is to consider your features, lifestyle, and personal preferences and to select a style that makes you feel confident, comfortable, and true to yourself.

By taking the time to understand the factors involved and experimenting with different options, you can find the perfect old-money hairstyle that complements your unique style and helps you project the timeless, sophisticated image associated with this enduring aesthetic.

Style Like a True Gentleman

Before we say goodbye, here’s one of the best-kept secrets in men’s styling circles, a secret that only a few expert image consultants know or are willing to share.

First and foremost, professional styling requires knowing your unique body shape and seasonal colour palette – paramount factors in choosing perfectly fitting clothes in colours that complement your skin, eyes, and hair.

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.

Best part? You can find your body shape, seasonal colour palette, and ideal fashion style in less than 5 minutes by yourself, for free, thanks to our four simple steps:

1. Find Your Body Shape

Different garments flatter different silhouettes, so knowing your body shape is the first step in dressing like a confident man.

To find out your unique body shape, take our free body shape quiz for men.

Once you know your unique body shape, take the second free quiz to discover your unique colour palette.

2. Find Your Unique Colour Palette

Remember, the garments that compose your outfits come in various colours, and you must ensure that each hue complements your natural colour.

To do that, you have to find out your seasonal colour palette, and you can do it by taking our free seasonal colour quiz for men.

3. Find Your Ideal Fashion Style

By now, you should already know your body shape and unique colour palette; the next step is to discover your ideal personal fashion style.

The fastest and simplest way is to take our free fashion style quiz for men; it includes your ideal style, outfit ideas, relevant fashion brands, and much more.

4. Professional Image Consultancy with The VOU

And if you want to style like a professional, by occasion, location, season, and time of the day, you can always ask our expert image consultants and fashion stylists for help.

Our styling services for men are the most comprehensive and detailed on the market, backed up by leading stylists who will guide you step by step in creating looks that communicate affluence, elegance, and endless accomplishments.

Remember, wearing luxury brands isn’t enough; to look stylish, confident, and successful, you must first know your body shape, colour palette, and ideal personal style, and only then style by occasion, location, season, and time of day.

Contact us today to save headaches, time, and money – it’s time to dress like a confident, successful gentleman of exquisite fashion taste – the first styling assessment is on us!