It is a cold afternoon in February 1963, and Bob Dylan is sitting in his tiny Greenwich Village apartment with his girlfriend and a photographer from Columbia Records. They’re trying to get a cover shot for Dylan’s new album, The Freewheelin’ Bob Dylan, and the usual schtick – Bob moody in chair; Bob moody in chair with hat; Bob moody in chair with hat and weight of a generation on shoulders – doesn’t seem to be landing. 

So, despite the dirty slush on the ground and the bitter New York wind, they head out to the streets to take some photos in the dying of the light. “It was freezing outside,” recalled Suze Rotolo, the singer’s then girlfriend, who in the final shot is seen hunched into her boyfriend with a sweet, youthful intimacy. And yet Dylan pulled on “that thin jacket”, as Rotolo put it – a gorgeous, butter-soft camel suede number, with collar half-up, buttons half-undone, shoulders high and square. It was New York in February. He was freezing. “But image was all.”

Dylan later told friends, when the album came out that spring, that ‘the cover’s the most important part of the album’. He may well have meant it sartorially, as much as anything else. As critic Janet Maslin once wrote: “It’s a photograph that inspired countless young men to hunch their shoulders, look distant and let the girl do the clinging.”

Fifty years on, as a new biopic of Dylan’s life, with Timothée Chalamet as the lead, begins production, it feels as though another generation of young men are about to come face-to-face with this moody, nonchalant, unhurried style. There is certainly a lot to be inspired by here – though with Dylan’s style, as with his work, all is not necessarily as it seems. The carelessness is carefully done; the individual garments, like words in a stanza, are chosen with a poet’s gut precision. 

A year or so before that Freewheelin’ shoot, Dylan’s aesthetic painted him as the consummate folk revolutionary — an earnest combination of heavy coats and worker’s caps. You can see it on the cover of his eponymous debut album from that year (1962), where Dylan stares out with puppy-fat sincerity from underneath a sheepskin coat (find yours at Saint Laurent) and a hat stolen almost directly from Woody Guthrie (try Dolce & Gabbana for similar). 

By 1965 however, Dylan had grown tired of the voice-of-a-generation tag and the navel-gazing of the folk movement, its down-home cosiness replaced with a more jagged, stark look and feel which coincided with Dylan switching from acoustic to electric guitar. Here, the mood appears more Parisian playboy than Dustbowl warbler — the hair ruffled up into a high bird’s nest; a black blazer over a sultry, polka-dot shirt. Think Tom Ford’s alligator-skin blazers this season; or Dior’s dotted, silken shirts, perhaps. There were sunglasses now, too — more curvaceous, Italianate versions of the Ray-Ban Wayfarer (updated today by Louis Vuitton or Valentino.) This was Dylan’s troubadour-esque take on the heartthrobs of the 1950s. In fact, he chose the final Freewheelin’ cover shot because it reminded him of an earlier portrait of James Dean.

A Gallic, vaguely androgynous feel creeps in here, as well — striped Breton T-shirts beneath the leather jackets; straight black jeans with black, Cuban-heeled leather boots — likely influenced by Dylan’s raucous European tour of 1966. If you now had to sketch a lazy caricature of a brooding rockstar, this would be it. But back then, Dylan was a true pioneer of the look, which was swiftly copied by Jim Morrison, Keith Richards and John Lennon, among others, and ran through the London punk movement of the 1970s right into the Upper East Side of the Noughties, with the grungy, skinny-jeans pose of The Strokes and their clique. If this riskier version of Dylan was in Chelsea today, he would be a regular at the seductive downstairs bar at the new One Sloane hotel, likely kitted out in Tom Ford tailoring and Rag & Bone denim. 

As his fame went global in 1966, Dylan’s look began to creep towards a sort of showman’s chic, with touches of Carnaby Street flair thrown in: on stage, he would frequently wear a dark green, jumbo-houndstooth two-piece, with oversized collars, drainpipe trousers and diamond-flecked stripes; or perhaps a more military-style jacket over broad black-and-white striped Beetlejuice trousers. We’re not in Kansas anymore, the look said, which was part of the joke. Dylan, the boy from Minnesota, never had been. 

Outfits and costumes were not accessories or afterthoughts to Dylan’s art, but part of its conception and expression. “When somebody’s wearing a mask, he’s gonna tell you the truth,” Dylan once said, and the songwriter’s style has been an extraordinary exercise in both mask-wearing and truth-telling. In the 1970s, Dylan’s staple look became a sort of playful take on Americana – with moments of pimped-out frontiersman chic, hippy headbands, lumberjack shirts and, on his epic 1975 Rolling Thunder tour, a sort of cowboy-clown mashup: Dylan with his face painted white below a wide-brimmed hat, with flowers and feathers tucked into its hatband. He was exposing America’s past while he wore it on his sleeve. The Hurricane, that 1975 protest song about the wrongful imprisonment of black boxer Rubin Carter which sums up this period, is like a tract of American epic folklore turned on its head. 

Today, at 82, the man still tours relentlessly and still packs out venues in every city he plays. He is a living monument from the peak of the last century. People don’t simply want to see Dylan, so much, as to have seen him – to have been in the physical presence of the greatest songwriter ever and attempt, perhaps, to absorb something personal from that physicality. “Somebody comes to see you for two hours, and they’ve come to see you,” Dylan told a reporter in Japan in 1986. “You could be doing anything up on that stage. You could be frying an egg.”

Dylan’s clothes and his style – which, of course, goes far beyond his clothes – must surely be a part of that allure. In preparing for perhaps his biggest role yet, Timothée Chalamet is said to have rented a house in upstate New York, near Dylan’s hallowed Woodstock, in order to get closer to his subject. Dylan’s style is also his substance, however. The actor might do better not to attempt to live like Dylan, but to dress like him instead.