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A Gentleman’s Guide

Six Ways To Wear A Leather Jacket

Whatever your style, we show you how to get the most from this wardrobe essential

  • Photograph by Mr George Elder

Worn as flight jackets in the early 1900s, thrust on to the silver screen by Mr Marlon Brando in The Wild One, and anointed as the uniform of hedonism by 1970s punk bands, the leather jacket has an illustrious history that spans more than a century. No wonder it’s one of the toughest items of clothing you can own; leather jackets have been through all sorts.

With brands now offering more styles than ever, there’s never been a better time to invest in one. But with choice, often, comes confusion. And how to don one in winter? From a Saint Laurent biker to a Thom Browne bomber, here is our comprehensive cheat sheet on how to carry off this rugged essential, whatever your style. (Tip: a few bumps and scrapes help.)


  • Photograph courtesy of IMAXtree

There are some men who can wear biker jackets exactly how the leather gods intended – thrown carelessly over a white T-shirt, teamed with black shades and a cloud of cigarette smoke. Mr Alessandro Squarzi, above – fashion entrepreneur, Instagram icon, esteemed member of our Style Council and Mr Charles Bukowski lookalike – is one such man. If you boast just half the masculinity of the firebrand poet and novelist, why not go hell for leather, too? Invest in brands such as Givenchy or Saint Laurent, and you’ll benefit from details such as asymmetrical fastenings and a diagonal zip, originally used by bikers to block out the wind. Sure, you bought yours from MR PORTER, but just tell people you found it abandoned in the dressing room of some careless punk band.

Get the look

  • AMIRI Leather Biker Jacket

  • Balenciaga Oversized Button-Down Collar Embroidered Cotton-Poplin Shirt


  • Photograph by Mr George Elder

If your style preference is a little more on the preppy side, investing in a varsity-inspired bomber with leather sleeves will add a bit of edge to your look. OK, it’s cheating a little, but not everyone wants to look like they’ve just parked up their motorcycle (some of us also have hair ill-suited to helmets). Wool is your friend in winter – a fact that Mr Thom Browne knows all too well, as he proves here with this slick design. Add some slim blue jeans and fingerless gloves, like this sensible gentleman on the streets of a chilly New York, and you’ll be positively toasty. Keep your cool, however, with a pair of black Wayfarers, the perfect foil to any pesky low winter sun. And if you’re headed to the office, a smart leather portfolio under your arm will look the business.

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  • Off-White Eagle Temp Appliquéd Wool-Blend Felt and Suede Bomber Jacket

  • Tomas Maier Mélange Cashmere Sweater


  • Photograph by Mr Tommy Ton/ Trunk Archive

Black isn’t necessarily best in leather jacket land. As long as you get the cut and colour of your jacket right, feel free to experiment with different masculine hues such as tan or grey. If you choose a shade brighter, just make sure you’ve got the guts to carry it off. Look at Tyler Durden in Fight Club. He rocks a red leather, and looks damn cool while doing it. This one, shot by the inimitable Mr Tommy Ton, is a fine example of breaking the mould. The fit is slim and the details are unfussy, making it more understated than a bulky biker. And the deep claret shade is rich and subtle, unlike Mr Durden’s bright red pleather number. Being an existential nihilist, however, we doubt he cared much for the provenance of his clothing.

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  • Prada Shearling-Trimmed Shell Flight Jacket

  • Officine Generale Mélange Cotton-Jersey T-Shirt


  • Photograph by Mr George Elder

If there were ever an icon in the leather jacket world, the accolade goes to the Schott Perfecto Leather Biker Jacket. Mr Irving Schott named the original Perfecto after his favourite brand of cigar, Mr Marlon Brando made it famous in The Wild One and Mr Sid Vicious requested he be buried in one. If the biker jacket were a person, it would be far too cool to sit with you. But nowadays, you don’t have to be a Wild One or a punk to pull one off. In certain situations, we sometimes find their shape a little severe, a little boxy. Wearing a hoody can relax things somewhat and soften your silhouette. Plus, the extra layer can act as a substitute for a winter coat. If you’re not so brave, may we suggest you look at these?

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  • SAINT LAURENT Leather Biker Jacket

  • Craig Green Lace-Detailed Bonded-Jersey Hoodie


  • Photograph by Mr Tommy Ton/ Trunk Archive

Unless you’re a spritely young musician, going all out by pairing a black biker with slim black jeans can sometimes fall flat. Dressing in just one colour can be unflattering, after all. Retired Japanese footballer Mr Hidetoshi Nakata, above, shows us how to wear a biker with dignity and style – by breaking things up with a pair of blue jeans and a few layers; note the white T-shirt peeking out from beneath his shirt. Adding a thick wool scarf only ramps up the sophistication.

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  • Hugo Boss Leather Jacket

  • Gucci Fringed Cashmere-Jacquard Scarf


  • Photograph courtesy of Thousand Yard Style

If you’re wedded to the idea of a leather jacket, winter can be a bit of a conundrum. You want to wear a slim skin, but you don’t want to freeze. So, why not slip on a down gilet? While we wouldn’t advise this under a biker (they are meant to have a snugger fit, and things will get a bit busy with the lapels, studs and zips), try adding one under a simple, roomy bomber. There are the obvious warming benefits, of course. Add a beanie hat and some casual sneakers, and you’ve built a whole new look with which to wear your favourite leather.

Get the look

  • TOM FORD Shearling-Trimmed Suede Jacket

  • Moncler Ever Light Quilted Shell Down Gilet

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MR PORTER or the products shown.