Did Bob Dylan’s Girlfriend Invent Bootcut Jeans?

When one pictures Bob Dylan, a few images likely come to mind: corkscrew curly hair, Ray-Ban sunglasses, perhaps a polka dot button-up shirt.

Those items hail more from Dylan’s mid ’60s era. Just a few years before that, he was often seen sporting a Greek fisherman cap, a jacket far too thin for the cold New York City weather and bootcut jeans.

But bootcut jeans — at least the widely available commercial type — did not exist when Dylan was wearing them. Levi’s and Wrangler, two of the most prominent jean designers in America, both introduced versions of bootcut jeans in 1969, several years after Dylan was wearing them, and that’s thanks to his then-girlfriend, the late Suze Rotolo.

The Origins of Bootcut Jeans

Technically speaking, bootcut jeans can be traced back much further than Dylan to the 19th century. Levi’s patented the first pair of blue jeans in 1873. Back then, jeans were not the common clothing item of today, found in just about everyone’s wardrobe, but usually associated with ranchers, cowboys, miners and other kinds of working men. These jeans needed to fit over cowboy boots and other kinds of labor-intensive footwear. In other words: bootcut jeans before the official title.

Suze Rotolo’s DIY Bootcut Jeans

Fast forward nearly 100 years to 1961, when a 19-year-old Dylan moved from Minnesota to New York City to pursue a career in music. Not long after, he met Rotolo, a young artist who introduced Dylan to a wide array of art, literature and people — and also helped him with his wardrobe.”

“His clothes were sloppy and didn’t fit his body well,” Rotolo said of Dylan’s style when she first met him, writing in her 2008 book A Freewheelin’ Time: A Memoir of Greenwich Village in the Sixties. “He wore shirts in drab colors, chinos and chunky boots, which later gave over to slimmer-fitting jeans and cowboy boots.”

That called for a clothing adjustment.

“I slit the bottom seams on his jeans and sewed in an inverted ‘U’ from an older pair so they would slide over his boots,” Rotolo wrote. “He is wearing them on the cover of the Another Side of Bob Dylan album. My solution was a precursor of the bell-bottoms that came on the market not too long afterward.”

Timothee Chalamet’s Jeans

Fast forward another 60 or so years to 2024, when Timothee Chalamet starred as Dylan in the biopic film A Complete Unknown. Naturally, Chalamet’s costume included the famed bootcut jeans. And if you wanted to achieve the look yourself, Levi’s launched a contemporary collection of 501 men’s jeans in the style of Chalamet/Dylan, complete with the ‘U’ shaped insert Rotolo invented all those years ago.

READ MORE: Opinion: Timothee Chalamet Nailed Bob Dylan’s Voice

It should again be emphasized that wearing jeans casually was not considered normal in the early ’60s.

“Jeans were relegated for construction or recreational work, like riding a horse, fishing, or playing wear on the weekends,” Arianne Phillips, the costume designer for A Complete Unknown, told Harper’s Bazaar in 2024. “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.'”

Or in Dylan’s words from 1965: “All I can do is be me, whoever that is.”