/The 12 Most Iconic Men’s Hairstyles Of All Time

The 12 Most Iconic Men’s Hairstyles Of All Time

A man’s hair has always been an important identifier of success; historically, it would denote class, wealth and masculinity. Now? Well, not much has changed. And despite some tweaks to length and texture, nor have the styles.

What looked good on Roman emperors still has the potential to flatter a modern mug. So take a lesson from these entries into the follicular hall of fame – the cuts that have somehow managed to transcend time and stay looking great – and maybe one day they’ll carve your ‘do in marble.

Alexander The Great’s Shaggy But Stylish

Alexander The Great

It’s not easy being in charge of the entire Macedonian empire. When you’re considering which Aegean territory to take over next, you don’t want to worry about whether it’s got styling mousse. For that reason, Mr The Great opted for a tousled, shaggy look that’s a particularly easy option for men with curly hair.

“This hairstyle is best worn pushed just off the face, and tucked behind the ears,” says Murdock master barber Alex Glover. This allows the natural direction of the hair’s growth to frame the face.

There are far more styling products on the market today than there were in 320BC, so if you have time, enhance the cut’s natural texture, by scrunching in a sea salt spray when drying – and then use a matte clay or putty for control.

If your battle uniform is a bespoke suit, your superior officer might confuse ‘texture’ for ‘mess’. So only copy this style if your workplace tends more towards neatly cut raw denim. Wear without a beard or any facial hair, like Alexander himself (he was famous for having the ancient world’s only clean-shaven army), or the overall look will appear untamed.

Modern Examples

Textured, Shaggy Hair like Alexander The Great

Key Products

Men's Textured Mid/Long Length Hair Products

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Brad Pitt’s Buzz Cut

Brad Pitt Buzz Cut

The noughties were a particularly regrettable decade in terms of men’s hair trends. We had big slicked fringes, frosted tips and that unsettling noodle thing on Justin Timberlake’s head. Unlike the others on this list, we’re not about to suggest those looks make a comeback.

Instead, Joe Mills, owner of Soho barbers Joe & Co, points to the current trend for military haircuts – worn best by hair god of the time, Brad Pitt, in around 2005 – as a modern alternative.

“The buzz cut has been seen on the catwalks for the last few seasons and has gradually filtered down as guys got bored of the short back and sides look.”

Named after the sound made by hair clippers, it’s a look than can be achieved at home if you’re after a uniform length, but for guys looking to camouflage scars or a protruding occipital bone, leave it to the professionals.

Modern Examples

Men's Buzz Cuts

Key Products

Men's Hair Products

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JFK’s Ivy League


Forget your gravity-defying pompadour and bushy sideburns – the real star hairstyle of the 1950s was the Ivy League. Also known as the Harvard Clip or Princeton, this classic preppy style is a slightly longer version of the military crew cut.

Popularised by style-god-in-chief, JFK, the extra length allows the wearer more scope for styling on top – traditionally into a side parting. Think Daniel Craig or Ryan Gosling’s shorter styles.

“In the 1950s and early 1960s, Ivy League universities had policies on how students should wear their hair,” explains Joe Pomper, a senior barber at Murdock in Covent Garden. “This style spread throughout the US in popularity and became a standard offering on barber’s boards.”

To recreate the look today, Pomper suggests asking the barber to use a grade five on the back and sides, blending downwards to a three and eventually a two at the nape of the neck. On top, have any excess length trimmed with scissors to keep everything neat, and style using a medium hold and shine product.

Modern Examples

Men's 1950s Ivy League Princeton/Harvard Clip Hairstyles/Cuts

Key Products

Men's Hair Products

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David Beckham’s Textured Falling Quiff

David Beckham

Arguably David Beckham’s best hairstyle, the textured falling quiff makes it onto this list for its contemporary classicism. Or classic contemporaneity. Basically, it will stand the test of time.

An ordinary footballer fade this ain’t. “Clippers shouldn’t be used here,” says Tucker. “The back and sides must be scissored for extra texture and less noticeable contrast.” When styling, take a paste and a pomade and rub them together in your hands.

Apply the products into towel dried hair with your hands, perhaps with a bit of salt spray for extra texture. “Then rake backwards, scrunching, to achieve that falling strand.”

It’s quite a floppy style, so works well with medium-to-thick hair with a slight natural wave. And wear it standing on the sidelines, rather than running about for 90 minutes or that volume will quickly collapse into a sweaty mess.

Modern Examples

Men's Modern Quiffs

Key Products

Men's Quiff Hair Products


River Phoenix’s Long Textured Hair

River Phoenix

Aside from bell-bottoms (shudder) and the rise of disco, the 1970s are known for being the decade in which men stopped being ‘men’ – by adopting long hairstyles for the first time in centuries.

And far more than a follicular flash in the pan, the trend stuck around well into the 1980s, when young stars of the screen like River Phoenix kept the look.

“This is a great era to take inspiration from at the moment, as it’s hitting the fashion world everywhere,” says Mikey Pearson, director of Manifesto barbershop in London’s Clerkenwell. “We mostly have Gucci to thank for that.”

To recreate this style, you need to ask the barber to cut in layers, which are great for adding softness and adapting the cut to different face shapes. “Always remember this rule: long hair must have long layers. It’s all about a visual balance, so you don’t end up with two haircuts in one,” adds Pearson.

A strengthening shampoo and conditioner will keep your trailing tresses in good condition, while a surf spray or texturising cream will add volume and definition.

Modern Examples

Men's Long Textured Hairstyles/Cuts

Key Products

Hairstyling Products For Men With Long Hair

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Jean-Michel Basquiat’s Short Dreads

Jean-Michel Basquiat

Jean-Michel Basquiat had a professional career that spanned just nine years, but the brilliance of his barnet is something that has lasted for decades.

The artist’s iconic short dreads continue to inspire afro haircuts to this day, reappearing on heads such as The Weeknd, but it’s not a look you can curate between Friday and Monday.

“Dreading hair takes time and work,” says Mills. “You have to twist and lock the hair. Ideally this is best done by someone who knows what they are doing – it’s not a DIY thing.”

Fortunately the upkeep of this up-do is something that can be done at home. “You need to keep twisting them and rinse your hair as opposed to shampooing,” adds Mills. Using a wax or moisturising gel will also help maintain the style and tame any rogue hairs.

Modern Examples

Dreadlocks Like Jean-Michel Basquiat

Key Products

Men's Hair Products For Short Dreadlocks

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Julius Caesar’s Face-Framing Crop

Julius Caesar

Caesar’s textured crop is as flattering as it is recognisable, not least because it’s a style that has returned to rule in recent years.

“The look is defined by the hair being trimmed to the same length all over,” says Glover. “This gives a gentle appearance to a man’s face.” Not to mention some imperial cheekbones. “To replicate the look, the edges should be naturally textured and not too neat.” So make sure your local barber doesn’t come over all Brutus with the scissors.

As a cut, it’s suited to those with thinner hair who want to give the illusion of thicker growth. To further this effect when styling, allow the hair to dry naturally after showering, then apply a soft finish hair product such as a styling cream, gum or wax.

Just don’t pair with a toga, no matter how classic your style.

Modern Examples

Modern Caesar Crop Hairstyles

Key Products

Men's Short Hair Products

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Cillian Murphy’s Disconnected Undercut

Tommy Shelby

A good haircut can define a man, but a great haircut can define an entire decade. Sure, a bad haircut can too, but we’re not here to talk about mullets or man buns.

Since swaggering onto screen in 2013, Cillian Murphy’s turn as Thomas Shelby in Peaky Blinders has made men get all misty-eyed about the 1910s in a way that hasn’t been achieved about age-old style since Mad Men. And one of the primary reasons is the show’s grooming.

“Men have moved from salons back to barbershops and as a result, traditional styles have become the go-to look,” explains says Liam Campbell, a senior barber at Nomad in Shoreditch.

More recently, hair trends have leaned towards slicked back styles with disconnected sides. But for a blinder of a barnet, Campbell suggests opting for a disconnected undercut. “Ask the barber to leave length on top, but take the sides in tight, preferably skin faded to add definition with a raw edge.”

Flat cap optional.

Modern Examples

Cool Men's Disconnected Undercut Hairstyles

Key Products

Men's Hair Products For Undercut Haircuts

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Elvis Presley’s Textured Pompadour

Elvis Presley

A little less slick-back action, a little more texture, please. Having been a trend for over a decade, it’s well-known that there are few grooming moves more stylish than the pompadour. But as Jones points out, it’s important to go for a modern version of The King’s iconic look to avoid getting stuck in a time warp.

“This look is not for everyone, as it’s a longer, more natural style,” he says. “It’s better for someone with thick hair and a natural wave.”

As an update, go for a short taper on the neckline and softer scissored texture on top, then apply a base product, like a cream, while damp before coiffuring your quiff. “Rough dry the hair with your fingers to get it into place and finish with a fibre – but you only need to apply a little bit.”

The style can fall out of place easily, so fix with a strong hold hairspray if you find your pomp falls flat before lunch.

Modern Examples

Modern Pompadour Hairstyle

Key Products

Men's Pompadour and Quiff Hair Products


Will Smith’s High-Top Fade

Will Smith

It’s difficult to imagine a time when hip-hop and rap music didn’t rule the charts, but in the 1980s it was just getting started. The the high-top fade symbolised hip-hop’s golden age and was worn proudly by many of the scene’s key players like Big Daddy Kane, Kid ‘n Play, and the Fresh Prince himself, Will Smith.

To get it for yourself, you’re going to need someone who knows their craft. “It’s become an art form that barbers try to perfect, and customers love the precision,” says afro specialist Richard Tucker from Ruffians Barbers. “It’s a great way to control thick, curly hair, but you’ll need to visit your barber every couple of weeks for top-ups to keep it looking its best.”

To style, use a bristle brush to keep any fly-away hairs in check, and then scrunch in a pomade to achieve a healthy-looking finish. If you’ve gone for a full-on high-top (rather than a low-top), use a hairspray and afro comb to properly shape and pat to keep in place.

Modern Examples

Modern Men's High-Top and Low-Top Fades

Key Products

Men's Afro Hair Products

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Liam Gallagher’s Brit Pop Mop

Liam Gallagher

Think of the 1990s, and your mind probably conjures up images of raves, ecstasy tablets, Brit Pop and Nicholas Cage action movies. What a time to be alive.

While curtains and bowl cuts were both immeasurably and inexplicably the haircuts du jour, Oasis frontman Liam Gallagher’s messy textured mop is what stands out as the ultimate style.

“Gallagher was arguably the coolest man of nineties Britain,” says Nomad’s Campbell. “His hair reflected his youthful rock ‘n’ roll attitude perfectly.”

Campbell adds that using photos for reference is key to helping a stylist or barber recreate this cut. “This is because the fringe and sideburns will sit differently on different hair types, but an experienced barber will know what to do.”

From there on in, some texturising products and a little IDGAF attitude is all you need to keep it looking good day-to-day.

Modern Examples

Men's 1990s Brit Pop/Mop Hairstyles/Cuts

Key Products

Men's Hair Products

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George V’s Slick Side-Parting

George V

In the current decade, the biggest men’s hair trends aren’t limited to what’s on top of the head. Since around 2010, every man and his dog has been growing a beard like a badge of honour, but few do it as well as George V.

“The King had a well-groomed style that would not look out of place in any decade,” says Alan Jones, from the eponymous grooming parlour.

It’s versatile, too. “The side-parting can be worn at different lengths, so is great in between cuts,” adds Jones, who also suggests tapering the back and sides for a more modern take.

To style, separate the parting using a comb and apply a wax or pomade with a slick look, or matte paste or clay for a natural finish. If your hair is particularly unruly, use a hairspray to set the parting in place.

To achieve facial hair fit for a king, run a beard oil through your facial forestry to condition, then use a moustache wax to bring definition to your upper lip.

Modern Examples

Greatest Men's Haircuts - Modern Side Partings

Key Products

Men's Short Hair Products

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