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How to dress like Bob Dylan

Updated on August 25, 2011

Bob Dylan's somber ways

Bob Dylan was the king of cool during the early-to-mid-1960's. While all the squares were all listening to Elvis and the teeny boppers listened to The Beatles, Bob Dylan was what all the cool kids were listening to. His songs weren't very catchy and he didn't look like a GQ model, but maybe that's why the 60's generation loved him.

Bob Dylan's style could best be described as somber. He wore mostly black mixed with earth dones, such as faded jeans and brown suede shoes. Nothing was too flashy about Bob Dylan. I think part of that blue collar, Minnesota working man aesthetic stuck with him, even though it was always clear he didn't belong in Minnesota. It's interesting to note that there's another Minnesotan who became a huge pop star and took style in the opposite direction: Prince.  

Let's take a look at some Bob Dylan clothing essentials: 

Ray-ban Wayfarers

Let's start right off with the most recognizable part of any Bob Dylan clothing ensemble, the Rayban Wayfarers. These iconic sunglasses have been worn by everyone from John F. Kennedy to Jack Nicholson to Andy Warhol. Speaking of Warhol, Dylan once had an affair with his muse, Edie Sedgwick, then wrote a song about it (Leopard Skin Pillbox Hat).

Although a lot of people have debated on the exact model of Wayfarers Dylan wore, I have it on good authority that he owned many different pairs. RB2132 was one of the models, but I have pictures of him wearing Wayfarers that definitely are not RB2132's. One thing that I have found is that Dylan's Wayfarers are almost always black.  

Long sleeve shirt with collar buttoned

Another typical Bob Dylan look is the long sleeve shirt with the top collar button buttoned. Although he rarely wears ties (although sometimes he sports a bolo), he almost never has his collar undone.

The color of the shirt changes depending on the period in Dylan's life. Early on he dressed more formally, often wearing a white dress shirt with a dark blazer or jacket over it. Later on he started wearing darker shirts made of heavier materials. In that famous video where he's in the limo being hounded by fans he's wearing a dark heavy workman's shirt with epaulets on the shoulders.  

Accessorize like Bob Dylan

The one accessory that I picture when I think of Bob Dylan is the scarf. He wore them often. He probably still wears them often. Checkered prints were popular. I've written a whole other page about the different ways you can tie a scarf. This is obviously something you'd only wear if it's cold outside. Dylan wasn't Steven Tyler, with an endless number of silk scarves and handkerchiefs in every color of the rainbow. As with everything else in Dylan's wardrobe, the colors and styles should be understated.  

An overcoat

Finally, one thing I see in lots of old Bob Dylan photos when he's not performing is an overcoat. An overcoat should be considerably longer than a blazer and come down close to your knees. Dylan wore gray or black overcoats, although sometimes he also wore herringbone tweed patterns. It all sort of goes with that poor man look that he was going for while remaining classy.  


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