Style | March 2, 2021 10:11 am

What We Can Learn From Bob Dylan’s Style

From classic tailoring tricks to patriotic power moves

Bob Dylan recording his album 'Bringing It All Back Home' in January of 1965
Bob Dylan recording his album 'Bringing It All Back Home' in January of 1965
Michael Ochs Archives/Stringer

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Bob Dylan is an icon in many departments. Firstly: music. With a catalogue of compositions that date back to the ’60s, his genre-bending sounds defied the scope of artistic conventions and, as a result, played a vital role in the explosion of countercultural and civil rights movements. With this in mind, Dylan’s societal musings also grant him iconicity through the written word: a fact that was driven home in 2016 when he was awarded the Nobel Prize in Literature. To this day, his cultural influence remains immeasurable, but there’s one other artistic sector he’s less known for but is still very much worth mentioning: his style.

For a man who has made a living on painstakingly honest streams-of-consciousness, it’s only natural that his uniform for expression has always been sharp, assured and authentic. Today, to celebrate a career that is now 60 years deep, Dylan is releasing a new compilation of his earliest recordings. So to mark the occasion, we’ve delved into the archive of his best style moments and handpicked eight of his sharpest sartorial ensembles. Bonus: they’re highly achievable for us all. Herewith, the icon’s leading style lessons …

Bob Dylan at a press conference at The Savoy
Fiona Adams/Alexander McQueen

1. Style starts with a touch of pinstripe

Dylan’s style has revolved a lot around classic pieces — and when it comes to print, one above all took center stage during his younger years: the pinstripe. Pictured above at London’s Savoy hotel in 1966, he embraced the refined pattern in trouser form, styling a skinny-cut pair with a suede blouson jacket: simple but very effective. Pinstripe is a swift way to slim and streamline your silhouette, and given that it never goes out of style, it’s a smart investment to instantly uplift your wardrobe.

Dylan recording his album ‘Bringing It All Back Home’
Michael Ochs Archives/Stringer/Husbands Paris

2. As for the base? Battered leather boots

Sure, the Beatles may have triggered the popularity of slightly heeled leather boots, but the longstanding appeal of these low-key glam shoes was thanks to the additionally cool musicians who pulled them off. Case in point: Bob Dylan, 1965. The little heel and long front of his footwear did much to seal the sharpness of his silhouette – and it’s likely that had he chosen another pair of shoes, his tailored ensemble wouldn’t have had half the effect. The best place to go to recreate his stance today? Easy: Husbands Paris.

Dylan, circa 1985
Dave Hogan/Versace

3. Western cues are important

In the 1980s, Dylan frequently nodded to his American heritage by way of Western style moves. Our favourite one? This fringed jacket. The obvious way to embrace this cowboy signifier is through a tan suede texture (still a big yes, FYI), but we’re guessing Dylan wanted to be a bit more in keeping with the rock undertones of his music, so he settled for a leather style instead. Rather than wearing it the normal way, he threw it over his shoulders for extra insouciance. Why not? This current style by Versace will allow you to channel this ensemble (just as long as you have the attitude to go with it).

Dylan on stage in 1974
Michael Ochs Archives/Drake’s

4. When in doubt, pull your collar out

Bob Dylan’s number-one style move to swiftly transition from day to night? An open collar. But we’re not just talking about undoing your top button here — we’re talking about pulling out your shirt to boldly sit on top of your jacket’s lapels. The beauty of this hack is that it works with pretty much any finishing layer, be it a leather jacket, denim jacket, or a single-breasted blazer. You can’t go wrong with a style move that will instantly transport you to the seventies.

Dylan recording in the studio in 1961 or 1962
Michael Ochs Archives/Stringer/Officine Générale

5. For full blown Americana, get yourself a plaid shirt

Musicians are a solid source of style inspiration for one main reason: their clothing choices are informed by their personal approaches to creativity. Take Bob Dylan’s early folk music. It was an authentic expression of his nationality, and from a uniform perspective, the best way of nodding to it was through a plaid shirt. Pictured here in 1962,  Dylan brought a good bit of nonchalance by unbuttoning said shirt, tucking it into some excellent straight cut jeans (best sourced secondhand, FYI) and grounding the look with leather boots. We can’t be sure on his shade of choice here, but for a failsafe move, stick to a dusty red design.

Nashville Skyline album cover
Columbia/Lock & Co. Hats

6. Never underestimate the power of a fedora

Dylan’s style might have been rooted in everlasting pieces, but as previously mentioned, but he often had a flair for accessorizing. Namely: wide-brimmed hats. His personal collection sits as one of the most impressive in musician history, mostly because he stuck to ultra cool, cowboy-inspired fedora designs in an array of colors: from black to white to khaki. Not an easy accessory to pull off, we will admit, but if you stick to an earthy tone and pair it with jeans and corduroy (like Dylan above), the effect is guaranteed to be good.

Dylan with his wife, Sara Lownds at Heathrow Airport, in 1969
Evening Standard/Stringer/Mr. P

7. Know your silhouette

The key to good style is consistency, and Bob Dylan has always had it because he understands the balance between silhouette and statement. He stuck to straight-cut, well-crafted items to streamline his slim body shape while still sparking some sartorial conversation through his selections in color and texture. No look better exemplifies this than his arrival to Heathrow Airport in 1969, when he wore a cinched-in, double breasted leather jacket over a crew-neck tee and some bright white denim jeans. The jean choice was key to selling this combination: cool, classic and oozing with casual pizazz.