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Gentleman’s Haircut: Stately Tresses for All Hair Types

Updated on August 14, 2024 by Karlton Miko Tyack · Uncategorized

What exactly is a gentleman’s haircut? You’d be surprised to know that a range of classy cuts is available.

Table of Contents

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  • What Is a Gentleman’s Haircut?
  • The Gentleman Haircut: The Classic Side Sweep
  • Long Gentleman’s Cut
  • You Can’t Go Wrong With Short Hair
  • Adding a Taper Fade to a Gentleman’s Haircut
  • Gentlemen Can Bald
  • Conclusion: Bring Out Your Inner Gentleman
Photo by AllaSerebrina / Depositphotos.com

Who do you look to when you think about gentlemen’s style? Perhaps old families, like the Delanos, Cabots, and Astors?

Maybe modern royals or past royals via paintings? Heck, you might even look at celebrity-style icons who exude a more old-world look.

Even in this varied group of potential examples, you’ll notice there’s a wide range of hairstyles. That’s because there isn’t one true gentleman’s haircut.

Dressing like a classy guy means a range of things, but they’re mostly anchored in tried-and-trues. Classy hairstyles and cuts are similar.

To demystify this vague terminology, we’ll first ask, what is a gentleman’s haircut?

Then, we’ll go into the different options for different personal styles and, of course, different hair textures. Trust me. Any man, no matter how refined you deem yourself to be or not be, can see themselves in this universe of classy cuts.

What Is a Gentleman’s Haircut?

Well, first off, what is a gentleman? For this exploration, let’s define him as one who exudes class. A man with a sense of culture, and politeness, all grounded in a strong sense of masculinity. 

That being the case, I consider gentlemen haircuts to be respectful, attainable, and flattering without showing deep vanity.

In fashion, a gentleman respects dress codes, goes for flattering fits, and incorporates understated ways of expressing himself. But, he never peacocks.

So, unfortunately for you gentleman punk rockers out there, we’re going to skip mohawks. Will also pass over hair that’s too long or any incorporation of shades that don’t occur in nature.

I’m not saying that rockers and rebels can’t be gentlemen (in fact, many are!). However, we’re going for a more particularly traditional aesthetic here.

So, with that scope, let’s explore some gentleman haircuts!

The Gentleman Haircut: The Classic Side Sweep

If there’s any cut that on can call the gentleman haircut, at least in Western society, it’s the classic side sweep. This haircut comes in many variants but you achieve it by parting your hair on one side and combing the top and side back.

The sides may or may not be cut shorter, but they’re definitely worn shorter or feature equally short volume as the top.

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So why do I consider this the gentleman’s haircut?

Well, practically every classic style icon, and by that, I mean those known for a traditional, never-changing look, has worn it. High society, politicians, and royalty also wear their hair like this.

I’m talking about movie stars like Cary Grant, royals like King Charles III. Also, modern-day celebs like George Clooney and Leonardo DiCaprio (when he’s going for a more traditional look).

Every James Bond wore this cut. Whether it was the traditional Connery look, the feathered ‘70s Roger Moore side part, or the close-to-head Daniel Craig look.

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Do you know who else wore this style? Legendary actors of the past, John Barrymore, and King George V. That’s the 1920s, guys.

It doesn’t stop there. Ulysses S. Grant wore a side sweep, as did Abraham Lincoln. We’re talking well over a hundred years of staying power.

Types of Side Sweeps

If you think the side sweep is too conservative, try any of these renditions.

Suppose you want a modern gentleman’s haircut. You can always go for a significantly shorter cut on the sides and keep your top hair moderately sculpted. Keep the part where it is, and make sure the less dominant side of the part stays back. 

If you have curly hair or wavy hair, you’re welcome to let the dominant side show some of that natural texture. You can maybe let it fall just a tad to the side, above your ear.

A gentleman’s haircut doesn’t have to be stuffy.

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You can also go for what is known as the Cosmopolitan or the Valentino. It was named after iconic Italian actor Rudolph Valentino, who slicked his hair all the way back.

It created an interrupted silhouette and required a lot of hair products. It’s like a clean, slicked-down version of what some might call a helmet head.

Kings of the past wore a side sweep called the aristocrat, which involved a winged silhouette where your hair meets your forehead. This was also worn with a middle part.

Long Gentleman’s Cut

When it comes to modern gentleman’s haircuts, there are ways to wear your locks longer than conventional expectations.

If you have super thin, fine hair, though, you might want to stick to shorter cuts. I’d give the same advice to those with hair that’s super curly and thick. Those types tend to grow up instead of down, and you can’t easily tame them with hair products.

To achieve a long gentleman’s cut, it’s paramount that you take good care of your hair. This means shampooing and conditioning. It also means ensuring you’re getting the ends cut so split ends aren’t forming.

Remember, there may be several definitions of a gentleman, but he definitely has self-respect.

While I love the beachy, sea salt look of a surfer, that might be a bit too casual. 

Part your hair to the side so that it looks like the beginnings of a side sweep, then let it fall naturally to the sides. Don’t let it get in your eyes.

A little texturing in the back, which a barber can help with by notching some locks, can add a classy structure. 

And most importantly, make sure to dress well. I know this goes without saying when you’re trying to look classy. But it’s especially important when you’re wearing your hair in this relatively casual way.

Again, this is a more modern approach to gentility — your grandparents may or may not approve of the longer hair.

You Can’t Go Wrong With Short Hair

Now, the other side of the spectrum. Whether you’re side sweeping your hair or parting it in the middle, showing off your natural hair type, or combing it down, you can’t go wrong with short hair.

Most non-dramatic cuts you could call classic gentleman’s haircut.
In fact, take a page out of the book of 1950s haircuts for men. Look at all of the short options. These are still valid today..

The regular cut, for example, is just a pulled-back side sweep. It looks great on any face shape and always makes you look neat and tidy.

The Ivy League is like a crew cut, but one that’s long enough to part on the side. Or you can avoid the part altogether, go for a longer crew cut, and add texture. You can even go for some slight, soft spikes (as long as they aren’t standing straight up, Bart Simpson style).

The college contour is another popular ‘50s cut that you still see today. It’s closer cut on the sides, with longer hair up top that’s then slicked back, or first parted and then slicked back.

Basically, gentleman hairstyles tend to be short because they work for all textures. When cut short, coarse, curly hair looks neat and is easy to maintain. Meanwhile, flat, thin hair doesn’t look stringy.

No matter the shortcut, the neatness exudes a level of taking care of oneself. 

Adding a Taper Fade to a Gentleman’s Haircut

Remember when I said that most non-dramatic shortcuts can look pretty noble? Well, when I say dramatic, I’m referring to hard, gelled-down textures, unnatural colors, and blatant fade. 

However, a taper fade absolutely works with any of the cuts mentioned above!

In fact, they add a fresh, immaculate look. Even if you aren’t using a product, a fade ensures the hair on your sides and by your neck isn’t haphazardly falling anywhere.

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A post shared by Unik Hair Design (@unikhairdesign)

Again, just make sure it’s a clean, gradual fade. Don’t go full bald at the end of the taper, or at least get it to the point where it’s difficult to tell if your barber gave you a zero-level buzz.

This type of fade looks great for those with coarse hair because it adds structure to your head’s silhouette.

Gentlemen Can Bald

Fortunately, there are many natural-looking treatments available today that can help with male pattern baldness. However, it’s absolutely nothing to be ashamed of.

Don’t comb your hair over in a way that a gust of wind would expose you, especially not in the front of your head.

Strong, talented, and well-respected gentlemen have sported bald heads. In fact, going back to the history of gentlemen, noblemen of past cultures often shaved their heads. Some Pharaohs, other African kings, and several past presidents sported bare heads.

Conclusion: Bring Out Your Inner Gentleman

When it comes to gentleman’s haircuts and gentlemen’s hairstyles, there’s a variety to choose from. Again, I maintain that the side sweep is the go-to, whether you’re trying to look like a man of leisure or a CEO.

And again, these days, you can definitely look classy with longer hair, but a short gentleman’s haircut is a failsafe. And a gent isn’t ashamed of his genes. If you’re bald, wear it proudly.

Which of these haircuts do you like the most? Most guys have style icons, but do you have someone you turn to for hair inspiration? Let me know in the comments!

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About Karlton Miko Tyack

Karlton Miko Tyack is a freelance writer covering watches, gear, and style. He was born in LA, studied art history in Boston, and is a lover of rugby, football, and optimism.

Background: Karlton studied art in Boston while working in local galleries. This led to a career in corporate art consulting, hunting down the perfect pieces for specific brand or business.

Transitioning into freelance writing, he moved back to his hometown of Los Angeles, where he managed top accounts with art publisher TASCHEN. His clientele included prominent names in fashion, luxury, and sports.

He then moved to NYC to work as a client liaison at Sotheby’s auction house in New York, where he worked with collectors of fine art, as well as watches, wine, and whiskey.

A lifelong watch enthusiast, Karlton has worked with quality timepieces of all price points and calibers, vintage and contemporary. Tyack’s watch obsession began when he received an Omega Seamaster for his 15th birthday.

Expertise: Through his work in fine art and with Sotheby's auction house, Karlton has developed a deep knowledge of timepieces, whiskey and menswear. He's written for publishers like LA Weekly and Harvard. Here at TMM, Karlton covers watches and men's fashion.

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