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.

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