15 Old Money Hairstyles for Men That Never Chase a Trend

Why the Classic Side Part Works for an Old Money Look

The Classic Side Part is the most literal reading of the look in this guide, with a defined part, the top combed across it and the sides short enough to keep the line clean. Cary Grant and Fred Astaire both wear it in the photograph below, and it is the cut most classic-style reference photographs are showing.

The clean line of the part and the short sides are what make it read as deliberate, which is the quality the old-money style is built on.

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 hold the part without springing back.

The sides are kept shorter, short enough to keep the parting line clean. Aim for a balanced volume that maintains the style’s structure without appearing too stiff or heavy.

Celebrities with Classic Side Haircut

• Jon Hamm wears one as Don Draper in “Mad Men”, with a sharp parting high on one side, the top combed flat across it and the sides cut very short.

• George Clooney wears the same part on grey hair, with more length left on top and no product shine.

• David Beckham has worn several versions of it, from a sharply defined part to a softer one with more movement in the top.

• 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 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

What this style needs is a medium to firm hold with a slight sheen rather than a shine, in a cream or a pomade that still combs through once it is in.

A light, flexible hairspray is optional. It is most often reached for in humidity or on hair that drops out of a part quickly.

Maintenance and Barber Visits

The part and the perimeter look sharpest in the first few weeks after a cut, and three to four weeks is a reasonable example to take to a barber. It is a preference rather than a requirement, and a slow growth rate will stretch it.

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

Explore all face shapes and style ideas

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

The Classic Side Part takes adjustment well. The length on top, the softness of the parting and the height of the taper can all be moved without losing the shape, which is why it sits alongside so many personal styles.

Why the Slick Back Works for an Old Money Look

What holds a Slick Back is the product rather than the cut, because the hair all goes one way and stays where it is put. A wet look is the finish most associated with it, and it is an option rather than a requirement; a matt paste gives the same shape without the gloss.

Clark Gable and Humphrey Bogart both wear it in the archive photograph below, each with a parting kept in, which is one of the two versions.

The Slick Back’s association with the old-money aesthetic lies in its plain, controlled shape and its long use with formal dress.

Ideal Hair Texture, Length, and Volume

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

The top needs to be long enough to comb straight back and lie flat to the crown, with the sides and back left a little shorter.

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

Celebrities with Slick-Back Hairstyles

• Leonardo DiCaprio wears a Slick Back as Jay Gatsby in “The Great Gatsby”.

• Michael Douglas wears a parted Slick Back as Gordon Gekko in “Wall Street”, combed flat with a high shine and no movement left in it.

• 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 a sophisticated appearance.

However, a well-groomed beard or moustache can create a more modern, edgy look.

Recommended Hair Products

A Slick Back is the cut here most often worn with a high shine, and a full wet look is one of the finishes it takes. For that, a strong-hold pomade with a glossy finish, or a firm gel for the wet look outright. For the same shape without the gloss, a strong-hold matt paste.

The taper fade, the pompadour, the quiff and the comb-over all have a polished version and a matt one, and each section says which product category gets you to which. What decides it is the finish you want, not a rule about the cut, and that applies to the Slick Back above as much as to any of them.

Maintenance and Barber Visits

Four to six weeks is a reasonable example here, and it is the length on top that decides it rather than the sides, because the sides are not cut short enough to show growth quickly.

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.

Why Ivy League Scholarly Chic is an Old Money Look

The cut takes its name from the Ivy League universities in the United States. What it looks like is a short back and sides with just enough length left at the front to lift into a small quiff, and a part that is combed rather than cut in. The wider Ivy League look is the wardrobe it usually appears alongside.

Ideal Hair Texture, Length, and Volume

Fine to medium hair with a slight natural wave is the easiest starting point for an 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 just long enough to lift into a small quiff at the front and no longer, so the height stays modest.

The sides and back should be tapered shorter, getting gradually closer towards the ears and neckline.

The precise tapering creates a clean, polished look, reinforcing the hairstyle’s crisp lines and refined silhouette in classic men’s haircut styles.

Celebrities with Ivy League Scholarly Chic Hairstyle

• John F. Kennedy wears the Ivy League in the photograph below, with the side kept short and enough weight at the front to hold a soft lift.

• Ryan Gosling wears a longer reading of it, with enough length at the front to fall forward rather than lift.

• More reference looks of this kind are collected in the guide to old-money style icons.

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, gently use your fingers or a comb to refine the quiff, 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.

A well-groomed moustache is the other common route, and it adds weight to the middle of the face where this cut deliberately keeps the hair short.

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

A medium hold with a matte or low-shine finish is what holds the small front quiff without making it look set.

A clay or a forming cream will both do that. Which of the two suits you depends on how thick your hair is, since clay is heavy work on fine hair.

A light hairspray is optional here too, for the same reasons.

Maintenance and Barber Visits

Three to four weeks keeps the front quiff at a workable length and the taper crisp, though nothing obliges you to hold to it.

If you do let it run longer, the taper is what shows first; the top simply becomes a slightly longer top.

The Ivy League haircut is a timeless old-money style with an understated finish.

Why the Taper Fade Works for an Old Money Look

What puts the taper fade in this guide is that the side gets shorter towards the ear and the neck gradually, with nothing in it that reads as a step. Taper and fade are both blended cuts and the words are used loosely, so asking for one or the other by name is not enough. What settles it is three details you can say out loud, namely how short the shortest part goes, how far up the head the change carries, and how much difference you want between that and the top.

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

Because the side is a gradient rather than a step, the taper fade sits comfortably in a formal setting at a low setting and reads more contemporary at a high one. That single choice is most of what you are deciding.

Ideal Hair Texture, Length, and Volume

The taper fade adapts to a wide range of hair types, textures and lengths.

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

The ideal length for the top portion of the hair will depend on your personal styling goals. A short top suits a textured finish, and a longer one gives room to comb it over or push it back.

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, aim for the proportions you want with your face and head shape, and check the result in a mirror once it is dry.

Celebrities with Taper Fade Hairstyle

• Justin Timberlake wears a polished taper fade in the photograph below.

• Ryan Reynolds wears a clean-cut taper fade with a little texture left in the top.

• Michael B. Jordan wears a sharper version, with crisp lines at the edges.

Styling Techniques

• Start with clean, towel-dried hair washed with a shampoo and conditioner suited to your hair 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

The fade itself needs no product at all, so what you buy follows the top rather than the sides.

For a textured finish, a matte clay or a clay-and-wax hybrid holds the shape without gloss. For a smoother finish, a medium-hold pomade with some shine. For lift with very little weight in it, a texturising spray on damp hair before either.

Maintenance and Barber Visits

Two to four weeks is a reasonable example, depending on your growth rate and how sharp you want the fade to stay. A fade shows growth sooner than a longer, softer cut does, which is the trade for how clean it looks when it is fresh.

Why Undercut is an Old Money Look

The undercut is the cut here that is defined by having no blend. The top keeps its full length and the side drops to a short uniform length in one step, with a visible edge where the two lengths meet.

That edge is why it sits in this guide and also why it needs keeping up. Everything depends on the join being cut cleanly, because there is no graduation to hide behind.

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 top needs enough length to be pushed back or swept to the side, because the contrast with the sides is the point of the cut.

The sides and back are clipped very short. On Wahl’s chart, a #1 guard leaves 1/8 inch (3 mm) and a #2 leaves 1/4 inch (6 mm), and some men go shorter still.

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

Celebrities with Undercut Hairstyles

• Brad Pitt wears an undercut with a longer top in the photograph below.

• Adam Levine wears an undercut with a longer, textured top and closely cropped sides.

• Cillian Murphy wears a vintage-style undercut, with the sides cut very short beneath a longer top.

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 works 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.

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

Recommended Hair Products

How much hold a long top over short sides needs depends on your hair. Fine or straight hair tends to drop out of the shape sooner than thick or wavy hair does, so start at the hold your own hair has needed before and adjust.

A firm, pliable clay with a matte finish gives the textured version. A strong pomade with shine gives the slicked version. Those are two completely different results from the same haircut, so decide which one you are after before you buy.

Maintenance and Barber Visits

The short sides are what date an undercut, so two to three weeks is a reasonable example for them. The long top will go further than that, which is why the two halves of this cut fall out of step with each other and why some men have the sides done between full cuts.

Why the Pompadour Works for an Old Money Look

A pompadour is defined by where the volume sits, swept up and back off the forehead and highest at the front, with the sides kept tight so the height reads as deliberate. Elvis Presley and Johnny Cash both wear one in the photograph below.

It is a demanding shape rather than a demanding haircut. The cut underneath is ordinary, and almost all of the work is in how you dry and dress it each morning.

Ideal Hair Texture, Length, and Volume

Medium to thick hair with a slight natural wave is ideal for a classic pompadour. The hair on top has to be long enough to sweep up and back and still hold height at the front.

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.

Celebrities with Pompadour Hairstyle

• Elvis Presley wears the classic pompadour in the photograph below.

• James Dean wears a pompadour in the photograph below.

• David Beckham wears a modern version of the pompadour in the photograph below.

Styling Techniques

• Start with damp, towel-dried hair and work a high-hold pomade or styling cream evenly through it, using the quantity its own directions suggest for your hair length.
• 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 a medium setting, directing airflow at the roots while combing the hair back to create volume and height. Height comes from drying the roots in the direction you want them to sit, not from turning the heat up.
• 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.

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

A pompadour wants a hold firm enough to keep height in the hair for as long as you need it, which usually means one of the stronger products in a range. Shine is a separate choice, with a glossy pomade for the polished version and a firmer cream with a sheen for a quieter one.

Water-based and oil-based pomades behave differently and the difference is worth knowing before you buy, but how much hold and how many washes any given tub needs is on its own directions rather than settled by which family it belongs to. A firmer cream is the third option, with a sheen rather than a gloss.

Building height takes more drying than combing a shape flat does, so this is one of the longer routines in the guide. How much product it takes is a question for the directions on whatever you are using and for how much hair you have, not something this page can put a number on.

On the dryer itself, nothing in this guide calls for a high setting. The American Academy of Dermatology recommends limiting blow drying and using low or medium heat with a heat-protection product, and a pompadour can be built on a medium setting with a round brush and a little patience.

Maintenance and Barber Visits

Three to four weeks keeps the sides and back tight enough for the height on top to read as deliberate.

Separately from that, this is a style you restyle every morning. The barber interval and the daily effort are two different commitments, and the pompadour asks for both.

Why the Quiff Works for an Old Money Look

A quiff is a smaller, softer version of the same idea as the pompadour, with volume at the front, but carried up and slightly forward rather than swept straight back, and left with some texture in it rather than combed smooth.

That is the practical difference between the two, and it is why a quiff takes less product and less drying than a pompadour does.

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 bring old-money polish 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 top needs enough length at the front to lift and turn back, and less towards the crown.

The sides and back are shorter, and how much shorter depends on the contrast you want.

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

Celebrities with Quiff Hairstyle

• Zac Efron wears a modern quiff with a textured, tousled top and shorter sides.

• Chris Pine wears a high, smooth quiff with the front combed rather than textured, which is the polished end of the range this section covers.

• David Gandy wears a quiff with a distinct parting at the side, which keeps a defined line there while the front holds its volume.

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 more rugged look.

For a more balanced look, consider pairing your quiff with a neatly trimmed moustache or goatee, which can complement the hairstyle’s mix of classic shape and contemporary texture.

Recommended Hair Products

For the textured modern quiff, a pliable clay with a matte finish. For the polished version, a water-based pomade with shine.

Either way, a pre-styling mousse or volumising spray before drying is what gets height into the hair while it dries, which is a different job from the product you finish with. How much height you can hold depends on your hair’s length and density as much as on either product.

Maintenance and Barber Visits

Four to six weeks is a reasonable example for the shape, since a quiff carries growth better than a fade does.

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

 Why the Crew Cut Works for an Old Money Look

A crew cut is short all over with a little more length left at the front than at the crown, so the top has a slight rise to it rather than lying flat. The sides are tapered rather than stepped.

What puts it in this guide is that it asks almost nothing of you once it is cut, and still holds a defined shape as long as the perimeter is kept clean.

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.

A crew cut keeps the top short, a little longer at the front hairline than at the crown, with the sides and back tapering down close to the skin.

The crew cut’s volume is minimal, as the short length keeps the hair close to the scalp.

There is almost nothing to arrange in the morning, which is the main reason to choose it over anything longer.

Celebrities with Crew Cut Haircut

• Ryan Reynolds wears a crew cut with the top left long enough to stand slightly forward rather than lying flat.

• Tom Hardy wears a crew cut with slightly longer hair on top.

• Channing Tatum wears a crew cut in the photograph below.

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 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 more rugged look.

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

Very little is needed here. A pliable cream is enough to tame short hair and give it a direction, and a matte clay does the same with more grip if your hair is coarse.

A matte or low-shine finish is the usual choice at this length, because there is not enough hair for gloss to read as deliberate rather than as damp. A little sheen from a cream is a different finish and is fine.

Maintenance and Barber Visits

Two to four weeks, depending on your growth rate and how short you keep it. This is the trade the crew cut makes, next to no daily styling but a shorter run between visits than a longer cut needs.

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

The crew cut is a timeless, low-maintenance hairstyle that suits the clean lines of old-money grooming.

What you get for that is a shape that stays tidy on its own between cuts, as long as the perimeter is kept clean.

Why the Buzz Cut Can Work for an Old Money Look

A buzz cut is a single uniform length all over, cut with clippers and no scissor work. It is the plainest cut in this guide, and the one that depends least on styling and most on the shape of your head and the state of your hairline.

What it has in common with the rest of this guide is that nothing about it is trying to be noticed, which is the quality most of the cuts here share; the undercut and the Edgar are the exceptions.

Because there is nothing to arrange, the only decisions left are the guard length and whether the edges are squared off or left to grow naturally.

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 length is simply the guard you choose, so pick it by how much scalp you are happy to show. Shorter looks starker, and slightly longer leaves a little to style.

Celebrities with Buzz Haircut

• David Beckham wears a buzz cut in the photograph below.

• Zayn Malik wears a buzz cut with a slightly longer top and faded sides.

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 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 more rugged look.

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, a few products help to keep your hair and scalp healthy.

At this length the hair does not need holding at all, so the products worth having are the ones aimed at the scalp, such as a light grooming cream or a moisturiser, and sunscreen on the scalp if you are outdoors.

A matte finish is the straightforward choice this short, since at a quarter of an inch there is nothing for a gloss to sit on.

Maintenance and Barber Visits

Two to three weeks, depending on your growth rate. A buzz cut takes no styling at all and still wants one of the shortest intervals in this guide, because at a quarter of an inch there is nothing for new growth to blend into.

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

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

Its fuss-free nature makes this cut a good fit for men who value a no-nonsense approach to grooming while still maintaining a stylish look.

Why the Comb Over Works for an Old Money Look

A comb-over is the side part’s less formal relation, with the same sweep across the head but the parting left where the hair naturally falls rather than combed to a set line. A side part does not need a line shaved into it either; that is an extra you have to ask for by name, and most of the cuts in this guide do not have one.

Its place here comes from the neatness of the shape, and from the fact that it hides a soft or uneven part line rather than depending on a sharp one.

The two versions differ in one place only, whether the sides are scissor-cut and left with weight or tapered short with clippers. Everything on top is the same.

That choice of sides is what lets the same comb-over sit with a traditional wardrobe or a more current one.

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 top needs enough length to sweep across to one side and lie smoothly.

The sides and back are kept shorter. Scissor-cut sides keep some weight, while clipper-tapered sides give more contrast.

The comb-over’s volume can be customised to the effect you want, from a sleek, flat look to a more voluminous, textured style.

Celebrities with Comb Over Haircuts

• George Clooney wears a comb-over with a soft side part, the top swept across with no product shine on it.

• Leonardo DiCaprio wears a comb-over with a subtle taper and a side part.

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 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 classic shape and modern finish.

Recommended Hair Products

A comb-over needs a medium to strong hold, and the finish is what decides which version of it you get.

A pomade with some shine gives the sleek, traditional comb-over. A matte clay of similar strength gives the textured modern one. The haircut underneath is the same either way.

Maintenance and Barber Visits

To keep a comb-over sharp, three to four weeks is a reasonable example for trimming the sides and back and keeping the top at a length you can still sweep.

The comb-over suits men who want a classic shape with a more modern finish.

 Why the French Crop Works for an Old Money Look

The French crop belongs here for the same reason the crew cut does. There is nothing decorative in it, and it holds its shape without being arranged.

A Caesar cut is the shape a French crop starts from, short all over with the top cut to a blunt fringe brought forward onto the forehead rather than swept back.

What separates the French crop from a Caesar is the texture. The fringe is cut with movement in it rather than as one blunt edge, and the sides are tapered rather than left uniform.

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 top needs only enough length to bring forward into a short fringe and texture with the fingers.

The back and sides are kept shorter and can be tapered or faded for a clean, modern look.

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

Celebrities with French Crop Haircut

• Cillian Murphy wears a French crop with a longer, textured top and shaved sides in the photograph below.

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.

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

The French crop wants texture and a matte finish, nothing glossy.

A sea-salt or texturising spray on damp hair first, then a small amount of matte clay or putty worked through with the fingers, is the whole routine.

Maintenance and Barber Visits

Three to four weeks generally keeps the fringe at the length that makes the shape work, with the back and sides tidy behind it.

Why Side Fringe is an Old Money Look

The side fringe is the least formal cut in this guide, and it is here because the shape is soft rather than styled. The length falls where it falls and the work is in the cut, not in the morning.

The difference between a side fringe and a side part is where the weight is. A part divides the hair and holds a line, while a fringe carries the length forward over the forehead and leaves the line soft.

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.

It is the furthest from the rest of this guide, and the one most dependent on your own hair, because a fringe only falls well if the growth pattern at the front lets it.

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 top needs enough length at the front for the fringe to fall across the forehead to one side.

The sides and back are kept shorter 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.

Celebrities with Side Fringe Hairstyles

• Timothée Chalamet wears a side fringe with a messy, textured finish.

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 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, separated 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 without overwhelming the hairstyle’s casual, effortless charm.

Recommended Hair Products

A saltwater or texturising spray gives the tousled version its grip and its matte finish.

For the smoother, defined fringe a light styling cream with a soft, pliable hold works better, since anything firmer makes the fringe sit in separated clumps.

Maintenance and Barber Visits

Four to six weeks is a reasonable example, and the fringe length is what you will notice going first.

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

It is the lowest-effort cut in this guide that still has length in it, which is the trade it offers, less styling than a quiff and less structure than a side part.

Why the Regulation Cut Can Work for an Old Money Look

Its short sides and defined outline are the features used for this example.

Show the reference photograph and discuss which details you want to keep or change. Use it to explain a style preference rather than assuming that the name identifies a particular military specification.

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.

Agree the actual lengths with your barber, with the top short enough to lie flat and the sides and back taken close to the skin, as in the photographs.

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.

Celebrities with Regulation Cut

• Jake Gyllenhaal wears a regulation cut as a US Marine in the film “Jarhead”.

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

Very little product is needed at this length.

A matte, high-hold fibre will give the short top some definition if you want it. If your barber finishes the neck and the edges with a razor rather than clippers, a lubricating shave cream matters more than any styling product for keeping that line between visits; some barbers use clippers throughout, in which case it does not.

Maintenance and Barber Visits

This is the shortest interval in the guide, usually one to two weeks, because a cut defined by a precise uniform length stops being that as soon as it grows.

It asks for no daily styling in return, so what it wants from you is a standing appointment rather than a morning routine.

Between visits, wash the hair regularly with a gentle shampoo to keep the scalp clean and healthy, and use a conditioner if your hair or scalp feels dry.

The regulation cut is the most exact shape in this guide, and the one that depends most on the barber and least on you.

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.

Why the Short Curtain Can Work for an Old Money Look

A short curtain is a centre part cut so that the top falls to both sides on its own rather than being combed there, which is why it needs length at the front and very little product.

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.

It belongs here because it is unstyled rather than styled, with no parting to hold and no hard edge to keep, so a few extra weeks show up as softness rather than as an untidy line. It still needs the shape trimmed back eventually, which the upkeep note below covers.

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 top needs enough length at the front to split at a centre parting and fall to either side.

The sides and back are kept a little shorter, 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.

Celebrities with Short Curtain Haircut

• Charles Melton wears a short curtain with a slightly longer top and a tousled, textured finish.

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, not disrupting 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 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

This style is about how the hair falls rather than how it is held, so the product has to be light, such as a moisturising styling cream or a non-greasy balm, enough to control frizz and define the ends without making the hair hang in strands.

Anything with a firm hold will stop the curtain moving, which is the point of it.

Maintenance and Barber Visits

Four to six weeks is a reasonable example for trimming the sides and back and keeping the top at a length that still falls to both sides. This cut grows out more gracefully than most here, because there is no hard edge in it to lose.

Between appointments, wash your hair with a gentle shampoo and conditioner.

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

 Why the Edgar Is Not a Traditional Old Money Haircut

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.

What it does share with the rest of this guide is the demand for precision. A blunt fringe and a clean fade both depend on an exact line, so they show growth sooner than a softer cut does, which is why the interval below is one of the shortest here.

Ideal Hair Texture, Length, and Volume

The Edgar haircut works best with straight to slightly wavy hair with a medium to thick texture.

The top needs to be long enough to reach the forehead and no longer than that, because extra length makes the fringe break into separate strands instead of sitting as one line. Your barber can judge that against your own hairline more accurately than a number can.

The sides and back are faded or undercut, with the length dropping away sharply so the fringe reads as a hard edge against them.

Volume is low. The effect comes from the straightness of the fringe line and the contrast behind it, not from height.

Men Named in Connection With the Edgar

• Kylian Mbappé, the French professional footballer, is often named in connection with the style. The photographs below show something else, a very short tapered cut with a lined-up front hairline and no forward fringe at all. He is worth keeping here for that reason, because it shows how loosely the name gets applied.

• Anwar Hadid, the model, wears a tousled, textured Edgar cut in the photograph below.

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, bring the hair on top straight forward, so the fringe falls in one line across the forehead. Where that line sits is a choice, because higher reads sharper and lower reads heavier.
• Use a blow dryer on a low or medium setting, directing the airflow forward and down so the fringe dries flat and lies in one line.
• If you want texture in the fringe rather than a solid block, work a small amount of matte clay or putty through it with your fingers before it dries.

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

A blunt fringe has to stay in one line, so this is a strong-hold style.

A high-hold pomade gives the sharp, sleek version and a strong matte clay gives the textured one.

Read the directions on whichever you choose. Some strong pomades are made to go on dry hair and behave nothing like the same product applied to damp hair, which is what the styling steps above assume.

Maintenance and Barber Visits

The Edgar depends on a straight fringe line and a clean fade behind it, and both go soft quickly.

Two to three weeks is a reasonable example for keeping the sides faded or undercut and the fringe cut back to its line, and it is one of the shortest intervals in this guide because the fringe is a straight edge and a straight edge shows growth quickly.

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

Which hairstyles work well with thinning hair?

• Short Crew Cut reduces the visual contrast between thicker and thinner areas.
• Buzz Cut makes uneven density less obvious and requires little styling.
• Regulation Cut keeps the silhouette controlled and avoids relying on a large amount of top volume.
• Textured French Crop can create visual texture without requiring a long, slicked-over top.
• Short Ivy League can work when density is still sufficient to maintain a defined top and controlled part.

Avoid using a comb-over simply to conceal progressive hair loss. If the hairline or crown is changing noticeably, a dermatologist can help establish what is happening and whether medical treatment is appropriate. Hair transplantation is another potential option for selected cases of permanent pattern hair loss, but it requires adequate donor hair and realistic expectations. The NHS also recommends researching the procedure carefully because a hair transplant is cosmetic surgery and results vary with the procedure and provider.

The American Academy of Dermatology’s hair-transplant guide explains candidacy, the procedure and the typical timeline for seeing results. The NHS also provides an independent overview of hair-transplant considerations and costs.

Face Shape

Looking at your own face is a useful step before choosing a hairstyle, though it is one input among several rather than a prerequisite. There is also an optional face-shape quiz if you would like one.

Five of the shapes are described below by what you can see rather than by the label. The reference guide linked above covers all nine.

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 with this outline, so choose by the effect you want rather than by any need to correct it.

Round Face Shape

Nearly equal in length and width, with a soft, curved jawline and no prominent angles.

If you want the face to look longer and more angular, add height on top and keep the sides and back short; if you like the rounder outline, fuller sides are equally valid.

Square Face Shape

Defined by a strong, angular jawline and a forehead approximately the same width as the jaw, not the narrower chin.

You can soften the angles with a slightly longer, textured top and a little length at the sides, or keep them on show with short sides; both are valid.

Heart Face Shape

Wider at the forehead and cheekbones, narrowing down to a pointed chin.

If you want less attention on a wider forehead, a side-swept fringe or a medium-length top that falls across the forehead does that; a beard can add breadth at the chin.

Diamond Face Shape

Widest at the cheekbones, with a narrower forehead and jaw, tapering to a pointed chin.

If you want the cheekbones to stand out less, add some fullness at the forehead and keep the hair close at cheekbone level; a haircut cannot add width at the chin, but a beard can.

A Practical Face-Shape Note

Decide what effect you want rather than trying to “correct” your face shape. If your face is visually rounder, some height and tighter sides can add length. If your face is long and you do not want to add length, keep the height modest and leave a little more fullness at the sides. Angular square features suit structured cuts if you want them on show, and with heart and diamond outlines some fullness around the forehead is one option; hair that ends at or just below the jaw can add visual width there, and a cut cannot change the jaw itself.

These are starting points, not rigid rules. Your hairline, forehead height, jaw width, ears, natural growth pattern and hair density can matter just as much as the broad face-shape category.

Hair Type and Texture

Your hair type and texture determine which old-money hairstyles work best. The main hair types are described below.

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.

Work with the wave by choosing styles that let it show, 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 keep 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 four below.

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

These styles take very little time in the morning and very little product, which is what makes them easy to live with.

Easy does not mean infrequent, though. The shorter a cut is, the sooner growth shows against it, so a Buzz Cut or a Regulation Cut will want the barber more often than a Slick Back does, not less. What you save with these four is daily effort, not visits.

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 four below.

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

These styles ask for daily styling with specific products and more time to get right, and they generally hold their shape between visits for longer than the very short cuts do.

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

Choosing by Hair Density and How Much Fuss You Want

Nothing in this guide is ruled in or out by your age. What does change with age, for most people eventually, is hair density and texture, and that is worth planning around because it changes what a cut can hold. The groupings below are about that, not about what you are allowed to wear.

If your hair is at its thickest

Dense hair holds contrast well, so the cuts that depend on a sharp difference between top and sides are the ones with the most room to work.

Four cuts that use that contrast.

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

All four depend on a visible difference between the length on top and the length at the sides, which needs enough density at the sides to hold a clean line.

If you want the least fuss for the most formality

These four give a finished, conventional shape without needing much done to them each morning, and none of them depends on a hard edge.

Four cuts that fit that brief.

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

All four sit comfortably in a formal setting and none of them reads as a statement, which is the whole point of them.

If your hair has thinned or changed texture

When density drops, a cut that relies on volume or on a heavy top has less to work with, and shorter, controlled shapes hold their outline better.

Four cuts that work with less density.

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

All four keep their shape without needing volume. The four do not all grow out the same way. The Ivy League, the longer-topped Side Part and the Short Crew Cut soften gradually, while the Regulation Cut has a defined line at the neck that shows growth first, which is why its own section asks for the shortest interval of the four.

What is the most classic old-money haircut for men?

The Classic Side Part and Ivy League are among the safest choices if you want a traditionally polished, understated result. Both can be adjusted for different face shapes, hair textures and levels of formality.

What is the best old-money hairstyle for thinning hair?

There is no single best haircut for thinning hair. Shorter, controlled styles such as a Crew Cut, Buzz Cut, Regulation Cut or textured French Crop can reduce the need to disguise thinning with excessive length. If hair loss is progressing, address the cause rather than relying on styling alone.

Can a fade look old money?

Yes, but the execution matters. A low or subtle taper generally fits the understated character of old-money grooming better than an extreme skin fade with a highly dramatic contrast. The goal is a clean transition rather than a haircut that dominates the overall look.

What haircut looks polished without being flashy?

A well-executed Classic Side Part, Ivy League, controlled Slick Back or neat Taper Fade can create that impression. The polished effect comes less from the haircut’s name and more from proportion, clean edges, healthy-looking hair and consistency with the rest of your grooming and clothing.

How often should I get an old-money haircut?

It depends on the cut, and the shortest cuts need the most frequent visits. Short fades and very precise styles show growth soonest, so a worked example is every 2 to 3 weeks, while longer, softer styles can often go 4 to 6 weeks. Neither of those is a rule, because your growth rate and how crisp you want the perimeter are what decide it. Daily styling effort runs the other way, with the shortest cuts asking the least.

Can a hair transplant help me wear more hairstyles?

For appropriately selected patients with permanent pattern hair loss, transplantation can restore hair to thinning or bald areas and may expand styling options. It is not suitable for every cause or stage of hair loss, and the amount of donor hair limits what can realistically be achieved. A qualified medical assessment should come before choosing a clinic or procedure.