"William Burroughs once said that On the Road “sold a trillion Levi’s.” The iconic denim brand is just one of the fashion companies to benefit from the disaffected, worn-out look popularized by the Beat Generation. The group of writers—including Burroughs, Jack Kerouac, Allen Ginsberg and Gregory Corso—were staunch anti-capitalists who railed against American materialism, but that didn’t stop them from setting the tone for style in the 20th century.

"Blue jeans, white t-shirts, workwear jackets and battered canvas holdalls were practical essentials for a life on the road, and they soon came to define the uniform for a generation of post-war youth disenchanted with traditional values. Along with counterculture icons like James Dean and Bob Dylan, the Beat writers spearheaded a look that became associated with alienation and rebellion. The movement—a reaction to mid-century, mainstream American society, which valued conformity and consumerism above individuality and freedom of expression—expressed their anti-establishment values through the way they dressed."

Article: How the Beat Generation Created the Uniform for Disaffected Youth