On The Road: Jack Kerouac and the Beat Generation's Style
On The Road: Jack Kerouac and the Beat Generation's Style
- Words Brenden Gallagher
- Date June 29, 2018
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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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.
The tension that was present in Kerouac’s wardrobe—a balance between the cosmopolitan life of the writer and the workaday look of an everyman wanderer—is equally present in his work. His best known work, On the Road endures as one of the great American road trip novels and continues to inspire restless teenagers today. In the book, Kerouac at once celebrates and critiques American life. He writes with admiration of the endless and endlessly varied American landscape, but he offers his sexual, social and spiritual critiques of the American way of life. Kerouac had a primal desire for the open road and he had that inexplicable bohemian desire to write about it. It is this fundamental contradiction, between the high-born world of the literary and the down-and-out world of the everyman, that would come to define his career. This was a tension that would dominate his work, his style and his life. Some say it is what drove him to an early death.
When we talk about Kerouac’s style, we are talking about what he was wearing when he found himself associated with the burgeoning Beat movement. This stretches through the period when he published On the Road in his mid-30s. Woolrich-style work shirts. Thick flannels. Bomber jackets. Work boots. Plain white T-shirts. It’s a style that wouldn’t be out of touch today in America’s hipper neighborhoods. The American legacy brands that are enjoying renewed interest like Carhartt, Dickies, Wolverine and Woolrich would have been the kinds of clothes Kerouac would pick out at local Army/Navy stores and leave rumpled in his closet. It is tempting to call this style timeless, but you have to note that before Kerouac, the style didn’t really exist. The style is timeless in part because of what he contributed to America’s menswear imagination.
Kerouac’s style has been called a “gesture of working class solidarity.” But if you come from a place like Lowell, Massachusetts, a “down-and-out burg where unemployment and heavy drinking prevailed,” like Kerouac, you know that it goes beyond an an aesthetic—it’s embedded from birth. Wearing the clothes of the working class isn’t a mere gesture if you’re from a working class community. It’s more than likely unintentional, but the effect squares the blue-collar vision of masculinity with the more cosmopolitan and fluid vision of manhood that comes from reading books, attending university, and finding yourself in the big city. Whether it was bowling shirts or bomber jackets, Navy-issue pea coats or painter’s coveralls, the melding of the fashion of the everyman with the aristocratic sensibilities of the artistic class signaled a new artistic moment in post-war America; Kerouac was at the center of it. This fascination with Americana was a signal that the time had come for new subjects, new perspectives and new journeys.
In his ode to Kerouac’s style at Mr Porter, fashion historian G. Bruce Boyer offered this assessment of the particular fashion revolution of the Beat’s cultural moment:
“‘Hip’ was the youthful point of view that emerged after WWII, as a counterweight to both the fear and conformity of a bleak past and a dubious future. Prole clothes and a laid-back demeanor formed its aesthetic correlative. The angry young rebels in the 1950s were the precursors of the new way fashion would work: not from the top of the social ladder down, but from the bottom up. Street clothes and work clothes—the gear of cowboys and ex-GIs, industrial laborers, the zoot suits of the jazz musicians that Mr Kerouac adored, and farm hands—would enter the realm of style. It was the style of the Underclass Hero, the Prole Rebel.”
It should come as no surprise that the denizens of Bushwick and Silver Lake still dress like a young Jack Kerouac; they are confronting the same tensions that he once did. America has changed in many ways since the 1950s, but young men still flock to big cities from small towns in Ohio, Montana, and Oklahoma with dreams of making their way as artists. At once, they want to leave their hometown behind and yet they spend their days meditating on their childhood in hopes of distilling their experience into the great American novel, or screenplay, or album or, hell, a blog post. At once they detest America—a familiar feeling in the Trump era regardless of your politics—and they see so much in it worth fighting for, worth saving.
This trend of young intellectuals taking inspiration from the working class has been derided as cosplay by some and analyzed as “self-conscious drag” by others, but that seems unfair. Yes, the image of the trust fund kid with a closet full of work boots was lampooned then and is still widely mocked today. But, that isn’t who Kerouac was. The contradictions between the romanticized writer’s life and the expectations of his working class background would haunt the writer until his death. Accounts of his final days tell a story of a man wrestling with his perceived shortcomings. Apparently, the acclaimed writer was still beating himself up for being dismissed from the Merchant Marine right up to his death. By a number of reports, he also succumbed to the bigotry and alcohol dependency that are stereotypical of a white working class background towards the end of his life. If that was cosplay, the miserable circumstances of his death were great lengths to take such a role.
Dressing in Americana (or, what we’d more broadly refer to as ‘workwear’) was as much a form of rebellion then as it is today. By embracing the clothes worn in ‘the rest of America,’ an artist class—particularly in New York City—is rebelling against Madison Avenue and Wall Street. Clothes like Kerouac’s prefigured the hippie movement in that they said to upper-crust observer: “I would rather live in the woods, work in a factory, toil on the farm, or not have a job at all than don the cookie cutter grey suits of Eastern seaboard suburbia.”
This sense of rebellion is perhaps best exemplified in Kerouac’s tendency to wear military issue and surplus clothing. Legendarily, he joined the US Merchant Marine, only to be discharged two weeks later. He left the service, but stuck with the style. A horsehide bomber jacket, Army issue trousers, engineer boots and other military surplus items would become staple of his personal look. Kerouac wasn’t the only one to incorporate the military look into his street style: The glut of military apparel being sold second-hand after World War II would become a symbol of the psychological battle of the itinerant wanderer. The clothes given to someone like Kerouac—provided for free to a serviceman, regardless of his tenure—would transform from a symbol of control, stability and literal uniformity into a metaphor for Kerouac’s own inability to fall in with the order and flow of modern society. When the Vietnam War endowed military surplus gear with a sense of national disenchantment, this (un)trend once worn by Kerouac would become a staple of American counterculture.
Laura Havlin at AnOther magazine argues that Jack Kerouac and Allen Ginsberg gave birth to the first “anti-fashion” trend. What Havlin and others mean by ‘anti-fashion’ is at the heart of what we would call ‘street style’ today. In Kerouac’s style, there is a sense that the fashion is created from the streets up, rather than from the runway down. In that desire for a ‘bottom-up fashion construct,’ is a respect for struggle. Authenticity has value and you want nothing more than get rid of the gloss. As saturated as these styles have become, streetwear and Americana labels are really only successful if they can certify and maintain their authenticity.
The same desires that led this generation to begin the American fascination with thrift shopping and second-hand stores defined this first major wave of American counterculture. In a 1952 New York Times article on the Beats, John Clellon Holmes wrote, “Any attempt to label an entire generation is unrewarding, and yet the generation which went through the last war, or at least could get a drink easily once it was over, seems to possess a uniform, general quality which demands an adjective…[Beat] implies the feeling of having been used, of being raw. It involves a sort of nakedness of mind, and ultimately, of soul.”
To call Jack Kerouac the father of street (or, perhaps ‘street-level’) style would go too far. There are too many style luminaries with a more conscious connection to the fashion world that have arrived since the Beat generation first started shaping American counterculture. What is fair to say is that Kerouac helped inject class consciousness to American style. He understood that when it comes to fashion, and all art, the tension between high and low, urban and rural, upper class and working class is an essential and timeless component to American life. A style that confronts these contradictions will always be more interesting than one that tries to hide from it. And in the way he dressed, as in the way many who were inspired by him would dress, he sought to illustrate exactly what side he was on.
The origins of the word “beat” in this context are murky. Thinking on the aformentioned New York Times piece, Holmes was elaborating on the words of Kerouac himself, who then was a little known writer, having just released an early, neglected novel. Fittingly, it had proclaimed, “You know, this is really a beat generation.”