On The Road: Jack Kerouac and the Beat Generation’s Style

“Take someone from 70 years ago, drop them on a city street today. Would their style fit in seamlessly with those surrounding them on the sidewalk? Styles change. The best dressed style icons of almost any era—no matter how respected—wouldn’t fit in to our particular moment without raising eyebrows. However, a small few manage to weather the twists and turns of style history, crafting a personal style that manages to remain relevant across time. For someone like Jack Kerouac, his scrappy mid-’50s style manages to resonate all the way into 2018. Esquire has called Kerouac’s fashion ‘casually elegant.’ GQ referred to the man as the ‘originator of blue collar cool’ and claimed he was one of the first ‘rejecting the notion that class was synonymous with value.’ The Beats presaged the ‘urban rustic’ moment that would happen early in the 21st century that resulted in the resurgence of numerous American legacy brands by melding the high with the low. Kerouac was one of the first cultural icons to master this balance with brooding grace. Kerouac was pulled in two different aesthetic directions. He was drawn to the self-consciously bohemian look of the Beats, characterized by dark colors, stripes and an effortless cigarette smoke tinged cool. He was equally swayed by the rugged look of Americana. It was the style of the lumberjack, the farmer, the factory worker, the painter and the military man that moved him. He combined these working class looks with the bohemian flavor of the beatniks to create what writers in the years after would call ‘anti-fashion’; today we would likely chalk this look up as ‘street style.’ While Ginsberg was known to sport a thrift store blazer and a second-hand tie, Kerouac looked every bit the part of the Americana wanderer. Together, they helped create a defining look in American counterculture. More specifically, Kerouac’s style was at once a homage to, and identification with, the American working class. …”

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