What made Bob Dylan’s jeans so cool?

On By Littum

How simple! How easy. There’s no rock and roll glamor in Bob Dylan’s look that says, “I’m a loud, larger-than-life slob.” Instead, the musician’s style was more “Bob” than something megawatt like The Stones or The Beatles. There was always a pair of worn blue jeans soldered to him, an aesthetic reminiscent of a high school sweetheart you’d skip class with. The simple yet captivating look is highlighted in the new Dylan biography A complete unknownreleased December 18 and starring Timothee Chalamet, who plays a young Dylan between the years 1961 and 1964.

The true base of style is his blue jeans, which indicate how Dylan’s uniform transforms. The jeans in A complete unknown was created by Levi’s and inspired by Dylan’s own denim from the brand. Levi’s Vintage Clothing and the film’s costume designer, Arianne Phillips, have also released a small capsule collection of jeans inspired by the iconic singer-songwriter. Available starting today exclusively at Levi’s Haus of Strauss VIP showrooms in LA, London, Paris, Tokyo and Mexico City, the collection includes 1955 501s with a bootcut insert, a “D” buckle belt and a suede jacket.

The slight changes in Dylan’s denim styles throughout his life signify how a very private artist reckoned with fame and even took advantage of his circumstances. When Dylan arrived in New York City in 1961 from his sleepy mining town of Hibbing, Minnesota, the musician’s wardrobe was charming and naïve. His clothes were wrinkled, as if he had snored on a bus for days or weeks, only to end up on someone else’s dirty mattress. “I found a couple of candid photos of him in 1961 and in an apartment where he crashes,” Phillips says over the phone. “And he sleeps on a mattress without sheets, and he looks like a disheveled boy in a wrinkled shirt.”

bob dylan levi's

Courtesy of Levi’s

In the early years of his career, Dylan channeled his idol, folk singer Woody Guthrie, donning a round of oversized Pendleton shirts, baggy carpenter pants and Red Wing work boots. Despite the uniform, there are little quirks to his simple workwear style, like a waxed jacket with a pleat at the shoulder seam on the sleeve and a button-down collar that pops out. He had often donned a charming corduroy cap. There would be the cuff of an unbuttoned sleeve, gaping as he strummed his guitar and blew into a harmonica. And let’s not forget the hair: A frothy coif of soft black curls that fell into a frontal bouffant that grew more voluminous as his fame grew. The dress is innocent, full of wonder – and it’s a look that’s easy to fall in love with. Dylan has always been the neighbor.

bob dylan levi's

Courtesy of Levi’s

But then again, the jeans were always his sartorial anchor, and while casual, they were also considered. Dylan’s 1955 Levi’s 501s were typically slightly altered with a hand-stitched insert that gave them a little flare. The detail was discovered by Paul O’Neill, the design director of Levi’s Vintage Collections, who learned about this craft in the book A Freewheelin’ Hour of Dylan’s first girlfriend, Suze Rotolo, the same girlfriend who appeared on the cover of his 1963 album The Freewheelin’ Bob Dylan. “In the early ’60s, when she (Rotolo) met Bob, she used to take his jeans, cut the side of them at the bottom, and she’d sew an inverted U panel from older jeans into the bottom, so they would slip better over his boots,” says O’Neill. “She basically created these bootcut jeans for him.” O’Neill and his team, who fitted denim for the film, recreated Dylan’s Rotolo-altered jeans for to sell to the public.

Dylan’s style changed as he became more of a superstar. Towards the mid-’60s, his youthful, baggy silhouettes became leaner and slimmer. “It (the new silhouette) is influenced by his travels and proximity to money and getting new clothes, and really mimics his confidence as an artist,” says Phillips, who notes that around this time Dylan went to London. An indicator of Dylan’s rise to fame and more daring fashion choices was a green polka dot shirt he wore to the Newport Folk Festival in 1965. “It may seem jarring, but it was a piece of costume that we loved because it really showed us where Bob has to go,” adds Philips. At this point, there were more sunglasses – and of course more hair.

bob dylan levi's

Courtesy of Levi’s

But there was another big denim moment when Dylan dipped his folksy toe into fashion: skinny jeans, specifically Levi’s Super Slims, which were impossible to find, even in Levi’s own archives. “They were the skinniest jeans you could make without using stretch fabric,” says O’Neill. “That’s what he’s wearing at the end of the movie when he turns into this peacock.”

While Dylan’s look was relatively laid-back, his choice to wear jeans throughout the early ’60s was a stroke of subversive rebellion. “They would have called ‘trousers’, which at that time you couldn’t wear jeans to school, you couldn’t wear jeans to church, you couldn’t wear them to the workplace. Jeans were relegated to construction or leisure work, which riding horses, or playing clothes on the weekend,” says Phillips. “The fact that he wore denim all the time was very unusual. And there were dress codes. You couldn’t wear them (denim) most places. Denim is really a signal of that young people are rebelling, in a ‘we’re going to wear these slacks wherever we want’ kind of way.”

musician playing acoustic guitar in a recording studio

getty pictures

These days there are endless conversations about personal style and how to achieve it. As for Dylan, he simply wore what he liked, changing or tinkering with his uniform in small but meaningful ways to suit his lifestyle. There were no major styling overhauls and no incredible transformations. Dylan grounded his clothes to the pavement – ​​or the stage – lived and breathed it and experienced life. The ultimate lesson? You don’t always have to be an outré fashion plate to make an impact. Sometimes a good pair of jeans is all you need.