Men’s 1950s Fashion – How To Dress Mid-Century Modern


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There’s a key moment in The Wild One, the 1953 youth-ploitation movie in which an outlaw biker gang runs rampant through Hicksville USA, when a starstruck girl inquires of their ringleader, an impeccably leather-jacketed, cuff-jeaned, scuff-booted, 1950s men’s fashion icon Marlon Brando, “Hey Johnny, what are you rebelling against?”

Brando’s response, with a world-weary sigh: “What’ve you got?”

The short answer, at least in sartorial terms, was: quite a lot. The early years of the decade were a style desert, a buttoned-up hangover of rigid post-war conformity in which even the maddest of men were trapped in grey-suit lockdown; but a great loosening-up had begun to occur by the time Brando roared into town.

Rock ‘n’ roll music, Beat poetry, and the abstract expressionists were leading the countercultural charge, and fashion took its cue from their let-it-all-hang-out ethos; cuts became looser, collars lost their starch, and elements of sportswear, workwear, and military uniform began to find their way into the everyday wardrobe.

What Is 1950s Men’s Style?

This was a time when some of today’s style staples – the turtleneck, the denim jacket , the knitted polo – were starting to come into their own, worn with an air of studied nonchalance, if not a sneer at the be-hatted corporate drones. But perhaps nothing symbolised the new, rebel-yell era more potently than the elevation of the humble white T-shirt.

Formerly a military-issue undergarment, it was suddenly draped across the decade’s most iconic chests; Brando got sweaty in one in 1951’s A Streetcar Named Desire, while James Dean brooded in one in Rebel Without A Cause (1955). Even Arthur Miller was pictured in one at his writing desk. “It became a kind of visual shorthand for rebellion,” says G. Bruce Boyer, fashion historian and author of True Style: The History and Principles of Classic Menswear, who was himself a teenager in the 1950s. “It represented the appropriation of blue-collar clothing for those who refused to buy into corporate society.”

James Dean

Meanwhile, rockers like Elvis Presley left more formal dress codes, well, all shook up, replacing trilbies with slick quiffs, ties with button-down shirts, and fusty flannels with featherweight fleck-linen jackets. Jack Kerouac and the Beats made a fetish of utilitarian workwear, both in their lives – in their plaid shirts and beat-up blouson jackets – and in their literature: “His dirty work clothes clung to him so gracefully, as though you couldn’t buy a better fit from a custom tailor but only earn it from the Natural Tailor of Natural Joy,” writes Kerouac of Dean Moriarty (inspired by real-life Beat hipster Neal Cassady) in 1957’s On The Road.

Leading the pack of unruly artists, Jackson Pollock sported splattered denim overalls when creating his epoch-making drip paintings: “A lot of artists in the 1930s and 1940s dressed like accountants,” says Boyer. “Jackson and his peers wanted to look like the antithesis of that.” In their decisive break with sartorial tradition, the 1950s rebels found their ultimate – and most enduring – cause. “They broke the mould,” says Boyer. “And we’re continuing to live with their legacy.”

What Does 1950s Men’s Fashion Mean Today?

“I wanted to try and push some freedom into the men’s collections,” Miuccia Prada has said, “and one of the best ways I found of doing that was to reference a time – the 1950s – when men first found the freedom to express themselves with their clothes.”

While many brands have rebooted the classic 1950s men’s fashion – high-waisted trousers, Perfecto leather jackets, Cuban-collar shirts , penny loafers – Prada have done more than most to keep the faith while adding a modern twist; witness their recent collaboration with Mr Porter that consisted of striped bowling shirts, checked Harrington jackets, graphic knitted polos, suede blousons, and loafers in Prada’s own Spazzolato leather. “The 1950s was a time of celebration and optimism,” said Mr Porter buyer Daniel Todd, “and the collection reflects that.”

PRADA x Mr PORTERPrada x Mr Porter

1950s men’s styles are also increasingly relevant at a time when traditional dress codes have broken down, and a well-placed knitted polo, textured sport coat, or pair of pleated trousers will add an air of breezy insouciance and smart-casual confidence to a work-or-play outfit.

“We’re at a similar point to the 1950s themselves, in some ways,” says the tailor and designer Timothy Everest . “Separates have largely replaced suits in most offices, so people need to find different ways to stand out. A lot of the shapes and patterns that are key to that – from the wider-leg trouser to the fine-checked blouson jacket – came to prominence in that decade.”


And other modern designers aside from Mrs Prada – Lucas Ossendrijver at Lanvin, Pierpaolo Piccioli at Valentino – have put their own spin on some of those looks, from printed satin bomber jackets to palm tree-print shirts. “The ‘50s styles laid down the marker for modern menswear,” Ossendrijver tells FashionBeans. “They can be reinvented again and again.”

But there’s another reason why 1950s men’s fashion is imperishable; more than half a century after Marlon Brando roared his way into cinematic history, they still carry a whiff of the subversive and the ineffably cool. From Cliff Richard’s urging us to move-it-and-a-groove-it in a drape jacket in 1958 (yes, he was a hepcat once) to a bequiffed Alex Turner donning a Saint Laurent varsity jacket in the 2010s, this particular revolt into style shows no sign of burning out.

As a contemporary issue of Life magazine declared, of the newly-minted species of teenager: “They live in a jolly world of gangs, games, movies , and music. They speak a curious lingo, adore chocolate milkshakes, wear moccasins everywhere, and drive like bats out of hell.” Be honest – sixty years on, who wouldn’t want to channel at least a little bit of that?

1950s Mens Lookbook

PRADA x Mr PORTER the kooples reiss mango man

Key 1950s Men’s Clothing

These are the key 1950s men’s fashion pieces that define the era and continue to inspire style today.

1. Cuban Collar Shirt

Nothing says ‘Havana blast’ more than this breezy summer, men’s casual staple, which can trace its history back to the 18th century in South America, where it was a kind of working-class uniform, though it really made a striped, checkered, and Polynesian-print splash in the 1950s, where it was seen on the back of everyone from Elvis to Montgomery Clift.

With its notch lapel-like collar (also known as a camp or revere collar), short sleeves, and straight, boxy hem, you could think of it as a classier take on the Hawaiian shirt. The modern variant has a more fitted cut and tapered sleeves; wear under a blazer for an off-duty Don Draper effect or roll the sleeves for the full Gene Vincent look. Reiss has a pretty good selection, both plain and printed, or try Timothy Everest’s bold-checked or white-weaved versions.

The Best Cuban Collar Shirts

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2. Pleated Trousers

Those who would see the 1950s fashion as a bastion of flat-front uniformity in the trouser department didn’t reckon with the hepcats or the rockabillies, who were saying “pleats please” decades before Issey Miyake got in on the act. “The early rockers borrowed heavily from the zoot suits that the jazz musicians of the 1940s wore,” says G. Bruce Boyer. “It was a colourful, exaggerated take on tailoring.”

Pleated trousers create elegant lines and a full silhouette (though any maxi-pleated ‘80s-style take should be avoided, unless you’re heading to a Kid Creole & The Coconuts-themed costume party), work equally well in a formal or casual context, and have the added summertime benefit of allowing air to circulate around the pins. E.Tautz has many versions on offer – the beige cotton chinos are particularly mid-century chic – while Kent & Curwen’s come in utilitarian tan.

The Best Pleated Trousers For Men

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3. 1950s Men’s Shoes: Penny Loafers

The classic slip-on shoes (the ‘moccasins’ referred to in Life’s breathless anatomisation of the teenager) has a chequered history – Norwegian fishermen and small-denomination coins factor in at various points – but, for our purposes, it’s enough to know that these shoes became the classic finishing touch for the Ivy League preppy look that blossomed in the 1950s, and that they’ve been gracing the feet of every well-dressed man since, from Paul Newman – who remains the only man to pair them with white socks and still look cool – to Tinie Tempah.

If you want to go full prep, team an original pair of Bass Weejuns with khakis, navy blazer, Oxford button-down shirt, and knit tie (no socks, natch) and avoid the ‘enhancements’ that various designers have felt moved to add in the ensuing decades – zebra print, baroque tassels, Cuban heels, backless iterations with fun-fur trim and so on.

The Best Penny Loafers For Men

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4. Knitted Polo

The original polo shirt, pioneered by Rene Lacoste, was designed in the ‘20s as a breezy alternative to the heavily starched, long-sleeved whites that tennis players had hitherto laboured in; the knit polo, developed in the 1950s in fine-knit cottons and cashmeres, was a breezy alternative to the shirt, with patterned versions conferring pizzazz and Riviera-readiness on their wearers.

For confirmation, check out Dickie Greenleaf, as played by Jude Law in The Talented Mr. Ripley, all stripe-panel polos, cuffed shorts, and suede loafers , an object lesson in dressing with corniche-owning, bebop flair. Modern-day Dickies can sip their dirty proseccos in retro-futurist versions by the likes of Scott Fraser Collection (sky blue L-stripe), Next (textured with contrasting white) and Uniqlo (plain emerald green).

The Best Knitted Polos For Men

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5. Blouson Jacket & Sport Coats

Where to start with the blouson? Starting out as the Harrington jacket, the sporty, waist-length, zippered, tartan-lined, elastic-cuffed mainstay was initially produced as one of the most lightweight rainproof golfing sport coats in the UK in the 1930s (the lining came courtesy of Lord Lovat, a British commando and keen putter who gave permission for his clan check to be used), but really took off after its export to the US in the 1950s, dovetailing with the trend for flight and bomber jackets worn by pilots during World War II and the Korean War.

It was taken up by the decade’s Holy Trinity of style – Elvis, Dean, Steve McQueen – and has since been adopted by subcultures from mods to soul boys and Britpop legends (take a lightweight bow, Damon Albarn and Liam Gallagher). You could do a lot worse than investing in an original Baracuta G9, but Prada’s satin number is a little more Drive, though at an investment-piece price.

The Best Harrington Jackets For Men

6. Leather Jacket

Nothing screams 1950s men’s fashion icons like Marlon Brando riding a motorcycle, sporting a sharp leather jacket in The Wild One, or Fonzie in his iconic leather jacket in Happy Days. Even Grease was set in 1958 and we all know how much those guys loved their leather. In the 1950s and ensuing decades, leather jackets have been a staple in men’s wardrobes as a dependable, easy to reach for option with a bad boy flair.

Leather jackets are just one of those 1950s mens fashion pieces that will never going out of style, probably because they’re the perfect companion for jeans to top off a cool look. When shopping for your own, invest in quality leather that will last you for many years to come, and won’t fall apart from all those motorcycles you’ll be riding.

7. Fedora Hat

The traditional fedora reached great heights in 1950s men’s fashion, and was the most popular hat at the time, mostly thanks to Frank Sinatra. Well beloved in 50s cinema and by fashionable young men of the decade, the fedora is still a timeless piece for any man’s wardrobe.

Adding an old school twist to any outfit, fedoras aren’t just for your dad’s friends. They’re sleek and stylish, with an air of mystery. Today, many men don stingy brim fedoras with a brim that’s less than two inches. But for an even greater effect, try out a generous, or wide brim fedora for a lasting impression.

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