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What Made Bob Dylan’s Jeans So Cool?

A new Levi’s collection celebrating the film A Complete Unknown answers the question

How simple! How easy. There’s no rock ’n’ roll glamour in Bob Dylan’s look that says, “I’m a loud, larger-than-life sugarpuss.” Instead, the musician’s style was more “Bob” than anything like the megawatt looks of the Stones or the Beatles. There was perpetually a pair of well-worn blue jeans soldered to him, an aesthetic reminiscent of a high school boyfriend with whom you’d skip class. The simple but captivating look is highlighted in the new Dylan biopic A Complete Unknown, out December 25 and starring Timothée Chalamet, who plays a young Dylan between 1961 and 1964.

The true style mainstay is his blue jeans, which indicate how Dylan’s uniform evolves. The jeans in A Complete Unknown were created by Levi’s and inspired by Dylan’s own denim from the label. 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 and songwriter. Available beginning December 20 on the Levi’s site, the collection includes 1955 501s with a bootcut inset, a D clasp belt, and a suede jacket.

The small changes in Dylan’s denim styles throughout his life signify how a highly private artist reckoned with fame and even tapped into his relationships. When Dylan arrived in New York City in 1961 from his sleepy mining town of Hibbing, Minnesota, the musician’s wardrobe was charming and naive. His clothes were rumpled, like he had been snoring on a bus for days or weeks, only to wind up on someone’s dirty mattress. “I found a couple of candid shots of him in 1961 and in an apartment where he’s crashing,” says Phillips. “And he is sleeping on a mattress without any sheets, and he looks like a messy boy in a wrinkled shirt.”

In those early years of his career, Dylan channeled his idol, folk singer Woody Guthrie, and was donning a rotation of oversize Pendleton shirts, wide carpenter pants, and Red Wing work boots. Despite the uniform, he tinkered a little with his simple workwear style, adding a waxed jacket with a pleat at the shoulder seam of his sleeve and a button-down collar popping out. He’d often put on a charming corduroy newsboy cap. There’d be the cuff of an unbuttoned sleeve that gaped as he strummed his guitar and puffed into a harmonica. And let’s not forget about the hair: a frothy coif of soft black curls that descended into a frontal bouffant that became more voluminous as his fame grew. The garb is innocent, full of wonder–and it’s a look that’s easy to fall in love with. Dylan has always been the boy next door.

But again, the jeans were always his sartorial anchor, and though they were casual, they were also considered. Dylan’s Levi’s 1955 501s were typically slightly altered with a hand-sewn insert that gave them a slight flare. The detail was discovered by Paul O’Neill, the design director of Levi’s Vintage Collections, who learned about this handiwork in the book A Freewheelin’ Time, by 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 met Bob, she used to take his jeans, cut the side of them at the bottom, and sew in an inverted U panel from older jeans into the bottom so they’d slide over his boots better,” O’Neill says of Rotolo. “She was essentially creating these bootcut jeans for him.” O’Neill and his team, who outfitted the denim for the film, re-created Dylan’s Rotolo-altered Levi’s jeans to sell to the public.

Dylan’s style did change as he became more of a superstar. Inching toward the mid-’60s, his youthful, baggy silhouettes became more slim and sleekly mod. “[The new silhouette] is influenced by his travels and proximity to money and getting new clothes and really mimicking his confidence as an artist,” says Phillips, who notes that around this time, Dylan went to London. One indicator of Dylan’s foray into fame and more daring fashion choices was a green polka-dot shirt that 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’s going,” adds Philips. At this time, there were more sunglasses—and, of course, more hair.

But there was another major denim moment as Dylan dipped his folksy toe into fashiondom: skinny jeans, specifically the 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 film, when he morphs 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’ve been called ‘dungarees,’ and at that time you couldn’t wear jeans to school, you couldn’t wear jeans to church, you couldn’t wear them in the workplace. Jeans were relegated for construction or recreational work, like riding a horse, fishing, or playing wear on the weekends,” says Phillips. “The fact that he was wearing denim all the time, everywhere, was very unusual. And there were dress codes. You couldn’t wear [denim] to most places. Denim is really a signaling of youth rebelling, in a way, like, ‘We’re going to wear these recreational pants wherever we want.’ ”

These days, there are endless conversations about personal style and how to achieve it. As for Dylan, he simply wore what he liked and altered or tinkered with his uniform in small but meaningful ways to fit his lifestyle. There were no major style overhauls and no incredible transformations. Dylan ground his clothes to the pavement–or the stage–living and breathing in them and experiencing life. The ultimate lesson? You don’t always have to be an outré fashion plate to make an impact. Sometimes, a great pair of jeans is all you need.

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