How to Dress Like Bob Dylan

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Bob Dylan in November 1963

Bob Dylan, 1963

When I was sixteen years old, I discovered folk music, & more specifically, Bob Dylan. I was a somewhat angry, emotional teen at the time, & felt outraged by all the wrongs in the world. I was also trying to find my creative groove, because I was learning to play guitar & I wanted to write songs, ones that weren’t cheesy sounding. I also wanted to try my hand at poetry, because I was working on being an author. I had just transitioned from being in my Beatles phase, where I obsessed over The Beatles & early 60’s pop, but had been finding happy-go-lucky melodies about holding people’s hands & other love-related themes a little too bland for my current emotions.

When I heard Blowing in the Wind, I finally found something which resonated with me. Hurt & angry & disappointed, but also strangely hopeful at the same time. Then I heard the songs Forever Young & Like a Rolling Stone. I was hooked. I knew I’d found something great, something that really spoke to me. Something angry, something passionate, something emotional that really shook me to my core & made me question who I was & how I felt about the world. I was enamored by the creativity & poetry of his lyrics, & the folksy non-conformity of Dylan as a person. I was also inspired by his style : rugged, windblown, honest, earthy; & then in his electric phase, sophisticated & sleek, & incredibly cool, in a rebellious, honest sort of way. Now, I could give a big rant about how awesome Bob Dylan’s music is, & how his work has influenced mine, but that will have to be a different post.

This article will be about how to work Bob Dylan’s signature style into your daily outfits. This is Part I, which will be about his folk phase. Part II will be about his style during his electric phase.


Bob Dylan's Folk Phase


From the time Dylan began playing in coffee houses, until approximately the Newport Folk Festival in 1965, when he “went electric”, his clothing style was simple, humble, working man’s attire. In this phase, Dylan was emulating his hero, Woody Guthrie, & therefore wanted a look which evoked the appearance of traveling hobos, migrant workers during the Great Depression, and a simple & less refined rugged honesty, qualities which were also present in his music at the time.

1. Plaid shirts. Plaid shirts in all colors will work great. Personally, I think red, blue, or gray plaid shirts capture the essence of Dylan best because they look the most rugged & add a nice masculine touch to the outfit.

2. Canvas / collared button down shirts. Earthy colors like beige or white are simple & best follow this look, but don’t be afraid to go for other colors as well. Remember, you’re doing your own take on his style, so adding your own touches, like a shirt in your favorite color, will make it even more authentic to what YOUR style is. As long as you add the unpolished, Woody Guthrie-inspired accessories like work pants and rugged boots, you will capture the vibe that you’re trying for. Although Dylan more commonly wore long sleeved button down shirts, if it’s warm out, you can always wear a short-sleeved version, or just roll the sleeves up. Personally, I love the look of rolled up sleeves. Masculine + rugged yet casual & pared-down.

3. Work Pants or Jeans. Black work pants are going to look the most like Dylan in his folk phase. I am personally a big fan of Dickies pants because they’re sturdy, quality pants, at a reasonable price. Because Dickies are actually work pants, they also add to the authenticity of the outfit. If you want to have the retro-esque “hard working” look of Dylan in this phase, wearing clothes that you could actually do labor in. Black jeans would also work, as would black shorts, especially black shorts which resemble work pants.

4. Work Boots. A good pair of work boots is a great thing to have in your clothing arsenal & can easily make any outfit a little more rough & tumble by wearing them. You could also wear another type of lace up boot if that’s more your style, or if you’re going for a very feminine take on the whole thing.

5. Brown Leather Jacket or Brown Fleece-Lined Jacket. Dylan wears a fleece-lined jacket, like the one on the right (in beige though), on the cover of his 1962 debut album, Bob DylanHe wears a different brown jacket on the cover of his 1963 album The Freewheelin’ Bob Dylanbut any brown jacket will work.

6. Newsboy Cap / Conductor Cap / Military Cap. Dylan wears a cap like this not only on the cover of his debut album, but also in many other photos from this era. The cap adds a nice little touch to the outfit, especially when paired with the style of turtleneck featured below. Very train conductor-ish.
7. Fisherman’s Turtleneck Sweater. Dylan is seen wearing this sweater in a lot of the same photos that he wears the conductor’s cap, & the combination looks very nice & cozy. I love turtlenecks in oatmeal / beige tones because they look simple, polished, & homey simultaneously, & very on-vibe with the worker aesthetic.

8. Duffel Bag Purse. A rugged looking purse, something along the lines of this, is a great purse to carry with any combination of the above outfits while still keeping with the feel of the outfit. I personally love the way the purse pictured looks because it appears sturdy, unpolished, & practical, & the combination of leather + buckles + canvas is a nice masculine touch.

If you were going to make this into a costume (or if you just want to add some real Dylan-esque vibes), add a harmonica + an harmonica holder, & an acoustic guitar. Or add those anyway, if you’re really feeling like a folksinger.

For more inspiration on this look, here is a video of Bob Dylan in 1963 playing Blowin’ in the Wind live on television.

And, a video of him playing A Hard Rain’s A-Gonna Fall in 1963. This video has a nice slideshow of photos from this era.

Read How to Dress Like Bob Dylan, Part II: The Electric Dylan.