How To Dress With 60s Swagger

Men's Fashion

There’s a famous quote, attributed variously to Dennis Hopper, George Harrison, and Robin Williams: “If you remember the ’60s, you weren’t there.” When it comes to menswear, however, it seems that the legacy of the 1960s is hard to forget.

The styles that came to prominence in that storied decade, from mod-inspired sharp tailoring to the dandy plaids and crushed-velvet loucheness of its latter, more decadent half, are still very much with us. Our primer on the legacy of ’60s style covers its movers and shakers, and looks at the pieces still leading the way today.

What Is 1960s Style?

One day in 1965, Michael Caine turned up at David Bailey’s studio to have his picture taken. The resulting image was so emblematic of its time that it might as well have had “The ’60s” emblazoned across it.

Caine faces Bailey’s camera, the characteristically punchy monochrome silhouette enhanced by his chunkily-framed glasses and the unlit cigarette dangling from his mouth (Caine had wanted to light it, but Bailey had assured him that “if you just leave it, it’ll look cooler”).

Michael Caine

The dark suit, white shirt, and slim dark tie are, of course, impeccable; but it’s Caine’s attitude that still smoulders, over half a century later.

“Post-war London was dismal and full of smog,” said Caine, “and then we had the shadow of the atom bomb hanging over us. So we looked around and thought, well, we might as well have a bit of fun then. And that’s when the ’60s started. It was no longer a case of the working-class knowing our place; we said, fuck it.”

No consideration of menswear in the 60s can afford to underestimate the power of those last two words. Yes, the great loosening-up had begun in the 1950s, with the birth of rock ‘n’ roll and the Beat Generation leading the countercultural charge; but what Bailey called “the Big Bang of the ’60s” changed everything.

The prime look, for Caine and his working-class-made-good peers, was haute-mod; Italian-cut suits, tab-collar shirts, whip-cord slacks and Chelsea boots, and an off-duty preppy uniform – navy blazers, Oxford shirts, woven polos, knit ties – that had looked so good on the ill-fated JFK on his downtime in Nantucket.


As the decade progressed, the outfits got more outre along with the drugs, whether it was the downtown-boho uniform of Breton tops and jeans sported by Andy Warhol and his cohorts at The Factory, or the dayglo colours, military tunics, and moustaches-and-mutton chops of the Sergeant Pepper era. But it was the dapper insouciance embodied by Caine that set everything rolling.

What Does 1960s Fashion Mean Today?

While other notions that gained common currency in the ’60s – free love, turning on and dropping out, circle chain belts – now look somewhat creaky and ill-advised, the menswear “Big Bang” it unleashed is still reverberating today.

Why? According to the actor and perennial mod Martin Freeman, it’s because “the beauty of the mod look that came to prominence then is that you can nick bits from here, there and everywhere – it’s a very broad church.”

Beams PlusBeams Plus

And its parishioners stretch from everyone who appreciates the cut of a well-tailored, slim-fit suit, whether bespoke from Savile Row – Michael Caine’s suits were made by Doug Hayward, another working class boy made good – or from high-street versions at Reiss or Suitsupply.

To those who opt for the more flamboyant late-60s dandy looks of the likes of Terence Stamp, Justin de Villeneuve and Lord Lichfield – the crushed velvet jackets, the white suits, the lace ruffs – now going down a storm at Alessandro Michele’s Gucci, where oversized lapels, eye-popping pattern, and Pierrot collars come as standard (and fly off the shelves).

Scott Fraser CollectionScott Fraser Collection

As for the preppy look, its variations are everywhere – as dress codes continue to break down, it makes a perfect halfway house between formal and informal – from the reverent homages by Japanese Ivy League fan-boy brands like Beams Plus and Camoshita United Arrows to the all-conquering polo shirts and varsity cardigans of Polo Ralph Lauren (and Mr Lauren, don’t forget, started his business back in 1967).

In fact, one of the biggest trends for spring/summer 2020 is what we might call avant-prep – oversized Oxford shirts at Prada, pixelated rugby shirts at Dolce & Gabbana – confirming that the spirit of ’60s experimentalism is very much alive and well.

Key 1960s Pieces

The Mad Men-Style Suit

How to be more Don Draper? A few gnomic utterances like “If you don’t like what’s being said, change the conversation” would help; a stack of identical, crisp white shirts in your office drawer will ensure you’re always prepared.

But the suit is the key; Mad Men’s visionary costume designer Janie Bryant dressed Draper in a fetishistic version of the classic ’60s corporate uniform – grey or blue suits, striped ties, geometric pocket squares – and kick-started the taste for smarter, more minimalist tailoring.

Try J Crew’s slim-cut Ludlow suit or Thom Browne’s ankle-flashing schoolboy take on the two-piece to emulate the look.

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The Cardigan

The ’60s was the decade when the cardigan shook off the shackles of pipe-and-slippers complacency and became hip, whether it was the mods frequenting Soho coffee houses and jazz clubs in streamlined suede-panelled versions, the preppies appropriating Ivy League varsity iterations, or an off-duty Steve McQueen rocking a shawl-collar cable-knit-white tee-Lee jeans combo.

Today’s equivalents are just as multifarious, from Gucci’s ebulliently-panelled varsity updates to Anderson & Sheppard’s lambswool shawl-collar cardigans in eye-catching colours. Even streetwear brands like Aries are getting in on the act with their just-this-side-of-Austin-Powers mohair paisley numbers.

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The Long-Sleeved Polo Shirt

The long-sleeved knitted polo was crucial to the original ’60s mod aesthetic, in that it was a still-smart alternative to a shirt and tie; it was sharp and streamlined with a collar that hung just-so whether buttoned or unbuttoned, and – crucially – it was logo-less.

That it looked the business back then under a three-button mohair jacket was a testament to its subtle smarts; that it looks equally efficacious today under a cashmere blazer makes it a timeless classic. John Smedley is undoubtedly the premier brand for the long-sleeved polo, now as then – try the merino wool or Sea Island cotton versions in everything from khaki to indigo.

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The Harrington Jacket

The sporty, waist-length, zippered, tartan-lined, elastic-cuffed mainstay had been around since the 30s – as the Baracuta lightweight golfing jacket – but was re-christened in the 60s in honour of Rodney Harrington, Ryan O’Neal’s proto-Mod character in the US soap Peyton Place. John Simons, an early Ivy League adopter, sold the jacket to the Mod fraternity at his legendary London store, which opened in 1955.

The original Baracuta G9 is still a top choice for Harrington purists, but luxe alternatives include merino wool versions from Timothy Everest’s new label MbE, and a lightweight version in a tech fabric from Dunhill.

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The Chelsea Boot

They’ve actually been around since 1851 (Queen Victoria wanted a laceless boot that wouldn’t get tangled up in her stirrups as she descended from her horse), but they changed from paddock boots to Chelsea boots in the ’60s after their adoption by the Beatles and the Rolling Stones (John Lennon and Paul McCartney requested that a Cuban heel be added to the design), and their ubiquity on the King’s Road.

Today’s urban warriors can take to that august thoroughfare in everything from Prada’s hardcore versions (with chunky caterpillar treads) to Common Projects’ more refined offering in a soothing shade of sand.

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