From the “video” for “Subterranean Homesick Blues,” which was actually part of the Dylan documentary Don’t Look Back.

In 1965, Bob Dylan was the coolest man in the world. That was the year he went electric, and while his folk-purist fans freaked out and yelled “Judas,” Bobby just stood around in an alleyway, littering incredible, enigmatic lyrics that might have been about civil rights, drugs, and the disenfranchisement of labor, or maybe just some talking blues about nothing at all.

His style was changing, too. 1965 was right about when he ditched his Woody Guthrie workwear look, and realized he had a thing for drainpipe trousers, shirts buttoned all the way to the collar, and Cuban-heeled boots, all worn with his signature messy mop (“Have you ever noticed that Abrahan Lincoln’s hair was much longer than John Wilkes Booth’s?” Bob once said in a mystifying defense of his long hair.)

Channel Bob’s mid-’60s rancor with beatnik-y menswear basics worn just a little bit askew: your hair in tangles, your boots all scuffed up. It’s a conservative little suit that, when worn with the knowledge that you’re the greatest songwriting genius the world has ever known, becomes downright outlaw.

J.W. Hulme Legacy Shoulder Bag J.W. Hulme Co. (You can find similar bags at a cheaper price at a thrift store or some equestrian stores.)
Can’t Stop the Beat by ruth weiss
Wayfarer sunglasses Ray-Ban
Vanessa Bruno shirt La Garçonne
Wool Quality Basic Waistcoat (vest) Scotch & Soda
Acne Kex low-rise skinny jeans Net-a-Porter
A.P.C. Tweed Blazer Coat La Garçonne (Look at your local thrift or charity shop for a men’s overcoat—it looks even better if it’s a little too big.)
Topshop Pomp2 Leather Chelsea Boot Topshop

(Again, you can find pieces similar to most of these for so much $$ less at a thrift store—and we recommend you do!)
Eugenia Kim Marina cap Net-a-Porter
Saint James Meridien II T-shirt La Garçonne
Presdales School Box Pleat Skirt John Lewis
Miltzen glasses Moscot
A.P.C. coat A.P.C.
Trouser Sock Barneys
Bringing It All Back Home CD
Ann Dexter-Jones bracelet
Dolce Vita JAX boots Lori’s Shoes