Grooming

Flattering Haircuts for Men Over 50 to Show Your Barber

We called on our go-to experts to give us the lowdown on what guys should be asking for in the chair.

by Zak Maoui

Published on Oct 1, 2026

As you get older, a lot of things change, and the hair on your head is one of them. It thins, it gets more wiry and, for many men, it goes grey. So how the hell do you style it in a way that's cool, but doesn't look like you're clinging onto the last days of your youth? You know the old saying about growing old gracefully? Well, it refers to your hair, too.


So, what should you be doing with it, if you've passed 50? We asked two of our go-to barbers for advice. Historically, men have often reached for the dye kit when grey hair started to appear – but these guys are all for leaning into it, looking to follicular North Stars like George Clooney and Idris Elba for inspo. Meanwhile, they know the tricks to keeping thinning hair flat, and making the most of a receding hairline, which as you get older, is one of those inescapable conundrums.

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The slick back

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Photo: Matt Winkelmeyer

"I love this look at the moment," says Max Oakley, founder of London-based barbershop chain Supply 91. "If anything it looks better on older guys. Looks great on silver hair and equally good if you have a full head of hair, or a receding hairline. Embracing the hairline is liberating. Think Walton Goggins: confident, masculine and comfortable. I recommend a hair paste on damp hair, then combing back with your fingers for a more tousled natural look. Top tip for any facial hair or stubble is to keep it groomed to balance out the more tousled look."

The warrior cut

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Photo: Steve Granitz

"The cut of the moment," according to Oakley. "I’d be remiss to forget this one. It doesn’t have to be the extreme ‘young’ look you see on socials. Instead, it can be a softer and more easily maintainable version. It’s also super easy to style, you can rough it up a bit with some paste and be on your way."

The short textured crop

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Photo: Stephane Cardinale - Corbis

A classic for a reason. This one is easy to wear and great for thinning hair because it adds plenty of texture and movement. You can also play with a bit of a fringe to conceal the hairline with this. Caspar Finch, stylist at Hershesons, agrees. "Create texture with a French crop - using a feather razor you can add loose shape," he says." He advises a shorter crop is great for thinning hair, which can also be helped with a texturing powder.

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The classic short back & sides

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Photo: Gilbert Flores

"It’s a timeless look- groomed and clean," says Oakley. "Keep a little more length and texture on top rather than going too tight. It’s a good choice for fuller, thicker hair."

The short natural afro

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Photo: Darren Gerrish

"Keeping the shape tight, especially on the sides, while letting the natural texture do the work," says Oakley. "My tip would be don’t try to make older hair look younger, work with the texture, the hairline and the greys, and make those things part of the look. Idris Elba shows how effective that can be, embracing the grey can add character, maturity and distinction rather than something to conceal."

The soft side-parting

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Photo: Alberto Rodriguez

"Older men fear the blow-drying element of styling their haircuts, which can make the hair look flatter." says Finch. "Instead, look to a George Clooney-style side-parting, which doesn't need it."

This story originally appeared on Esquire.com.


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