Secret Style Icon: Bob Dylan in 1965

No one has ever looked cooler. I’m sorry but it’s just true.

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


  • genina December 6th, 2011 7:10 PM

    Love iiiitttt. Definitely keeping these outfit sets in mind from now on—I’ve loved his style for years. <3

  • posh_lacrosse December 6th, 2011 7:13 PM

    this is an amazing post! i love bob dylan’s music, but i don’t know he was such a style icon. now i have new ideas for my outfits.

  • Fortune_Goddess December 6th, 2011 7:20 PM

    Ahh! I love Bob Dylan! Amazing man and musician. I was surprised to see two STYLE posts in a day, though…

  • taylortarantino December 6th, 2011 7:25 PM

    ASDFGHJKL:” I am so happy you made a Bob Dylan post. He is my role model and my secret husband! I am just so utterly pleased with this!

  • chloelrd December 6th, 2011 7:55 PM


  • Tracy December 6th, 2011 8:03 PM

    I love this post! I’ve been really into Bob Dylan lately (especially circa 1965).

  • Stefania December 6th, 2011 8:44 PM

    This reminds me of a photo shoot I did where I staged a date between Bob Dylan and Janis Joplin!

    You can see it here:

  • burn-your-flesh December 6th, 2011 10:04 PM

    This is so wonderful.

  • bohobambi December 7th, 2011 1:36 AM

    He looks so young and cute in that red striped shirt! Love this style post. :)

  • Lotta December 7th, 2011 4:02 AM

    this is cool :)

  • FashionHauties December 7th, 2011 9:45 AM

    I love his style. It is so classic and kind of reminds me of a small Perisian feel. I love the subtle boat theme (the stripes, the hat) and definately laid back vibes are apparent. His style is definately timeless.

  • missblack December 7th, 2011 2:18 PM

    oh Bob Dylan, you are the coolest, with your skinny body and your smoker’s voice and your beautiful poetry and your crazy hair.

    If I ever took to dressing like a man I would definitely do it like this.


  • yourenotfunny December 7th, 2011 3:58 PM


    oh Bob Dylan, coolest guy on Earth…

  • Notgoingtotrytohard December 7th, 2011 9:47 PM

    LIKE DYLAN IN THE MOVIESSSSSS…. * me singing horrendously I friggin love belle and sebastion

  • queenoftherats December 8th, 2011 2:23 AM

    i will never be able to deal with how perfect bob dylan is

  • Renatotherescue December 8th, 2011 12:12 PM

    oh gosh this is my facourite rookie-blog ever!
    i LOVELOVELOVE bob dylan, he was SO CUTE in the mid-60′s ;3
    i kinda mis his genius striped trousers and his clownie- polkadot blouses
    and ofcourse that video of him in newcastle where he bought a pink tie TEEHEE \
    i have a plain white tee with the picture of him in the back of a car, wearing sunglasses and smoking a sigarette, and through the car-window you see a girl looking at him like she is in love
    thats my favourite shirt :3 im wearing it right now!

    XX thanks for this!

  • insteadofanelephant December 8th, 2011 12:57 PM

    bobby d is my boy. just acquired a ton of vinyls from my roommates parents, now he’s singing to me all day everyday

    instead of an elephant

  • MechaMech December 9th, 2011 12:19 PM

    This is pretty awesome. I’m and old, old lady at 22, and I totally had a Dylan phase when I was like 16. Seems like it’s a universal thing! (I still love him, though. Even if for some reason I started completely loathing his music [I don't], he would still hold a sizeable chunk of my heart because of those years.)
    Also I’m getting Wayfarers for Christmas. Hell yes.

  • soybrain December 10th, 2011 9:42 AM

    bobby dylan! what a guy. I’ve never seen him in the fashion way though. interesting piece ;)

  • SkillzBeat December 12th, 2011 1:31 AM

    I got so excited when I saw that the secret style icon was Bob Dylan! I love him and his music so much, and I SO love his 1965-66 look! Thank you for this post!

  • Sailor-g December 14th, 2011 12:49 AM

    Hei, vil bare si at du inspirerer mange unge i Norge også :) leste en artikkel om deg der det sto at du kunne norsk flytende, så jeg prøver meg.. Elsker Bob Dylans stil, musikk og politiske standpunkt! og liker veldig godt at du skriver om han, stå på !


  • rroseselavy December 24th, 2011 10:44 AM

    THIS IS SO WONDERFUL. (And I really want a jacket like his on the freewheelin’ cover.) Thank you so much for this!

  • warpaintfiend May 6th, 2013 4:53 PM

    I’ve recently been obsessed with Bob Dylan so seeing this just made my day. I need to get my hands on some chelsea boots dammit!