Bibliophile Style: Jack Kerouac

There was a time in my life when I was obsessed with Jack Kerouac — which is another way of saying that I was once a man in his twenties.

I first came across On The Road when I was about 18. A real sweet spot, in other words, for Kerouac appreciation. I had recently graduated high school and had gone off to university in a faraway place, with the prospect of a whole new life just coming up on the horizon. What’s more, I was studying English lit, which meant discovering on a weekly basis books and authors I had never heard of, each representing the possibilities of endless worlds to discover, both real and imagined.

No book captured the nascent possibilities and boundless potential of those heady days better than On The Road. The title alone evoked a sense of motion and potential, while every sentence bristled with kinetic energy and the excesses of youth. Reading it felt like a rite of passage, an awakening to all that the world has to offer. Just as Kerouac had written it in a single, feverish writing session, I remember reading it all in one go in a similar fit of inspiration…

…Or did I, really? That’s the thing about Kerouac and the book that turned him into an icon: it’s easy to get a little carried away when talking about them. Looking back on it, I was actually a pretty slow reader and rarely got through anything in one sitting, so it seems unlikely that I’d have managed all 400-odd pages of the so-called original scroll (the first version of On the Road I read) in a single attempt.

That’s not the end of it, either. The truth of my own biographical situation while reading about Kerouac’s real-life exploits paled comically by comparison. While I was living out a fantasy of cross-country road trips and drugged-out excesses, in real life I was nothing but a library-bound, rule-following wallflower. Moreover, while entertaining fantasies about the nomadic, rock and roll lifestyle I could lead in imitation of my new hero, Jack, I barely ever touched a drink and had never so much as sat in the driver’s seat of a car.

It took me a few years to realise that Kerouac’s literary powers had seduced me into imaging a future that in no way reflected my personality or preferences. While Jack may have revelled in his drug- and booze-fueled adventures, I eventually clocked that generally I preferred kicking back with a nice cup of tea and some Seinfeld re-runs. While it is true that I, like everyone, enjoy a good road trip, I now know that I much prefer the comforts of a well-appointed AirBnB and a considered itinerary to being dragged out of bed at a moment’s notice by some or other angelheaded hipster.

Around when all of this first dawned on me was also the last time I read On the Road. I was probably in my late twenties by this point and, despite now being the actual age of the book’s protagonists, this time around I didn’t really get into it. The seductive momentum of Kerouac’s prose was still there, but I kept getting caught up in all the things that were excluded from his percussive sentences: the families these carefree men left behind to fend for themselves, or the sad fate of the author who would drink himself to death well ahead of his fiftieth birthday.

It’s fair to say, then, that I have long since fallen out of love with the Kerouac persona and what it represents. What has remained firmly intact, however, is just how much I like his clothes.

Thinking back on it, it’s likely that Kerouac’s wardrobe was every bit as appealing to my young brain as was his writing. I remember taking every Beat-related book I could find off the shelves of my college library — not to read them, but just to flip through to the glossy photo pages where I would covetously pour over the clothes worn by Kerouac and his cadre.

I liked the look of all of the Beats and tried to immediate each of them in turn. Lucien Carr, Lawrence Ferlinghetti, Kerouac’s muse and co-conspirator, Neal Cassady, of course. To this day I wear glasses similar to Allen Ginsberg’s horn-rims, all while holding out hope that I might eventually pull off a three piece suit like William S. Burroughs could. But ultimately these were all just dalliances; Kerouac was always the one I kept coming back to.

The Beat Generation was the first to incorporate workwear and militaria into their everyday wardrobes for non-utilitarian reasons. Since surplus items were easily procured for little money from Navy or Army stores, these cash-strapped and carefree types duly transformed former working garments into an enduring uniform of youth.

Kerouac was the perfect model of this beatnik aesthetic. Look at just about any photograph of him and you’ll see a man covered head-to-toe in garments that any vintage dealer would likely give their front teeth for in exchange. He was particularly partial to hardy work shirts, thick flannels, military issue chinos, practical blouson-style jackets, and hardy athletic wear. His sleeves were usually rolled, his top button undone, his collars crumpled, and a notebook and box of cigarettes perpetually stuffed in his pocket. Even when pictured wearing a suit, he looked like he was seconds away from loosening his tie and swinging the jacket over his shoulders. It’s the stuff of a million calculatedly carefree fashion shoots to come.

Of course, part of the lasting appeal is that on Kerouac these garments looked entirely fitting and not the least bit affected. It also helped that he always had the air of someone whose appearance was but an afterthought — a common occurrence among those blessed with matinee idol looks, and a youthful Kerouac had those in spades. 

Of course, it’s unclear to what extent all of this apparent authenticity was actually accurate. On the one hand, Kerouac’s clothing was perfectly in keeping with his humble roots. He also tried to join the U.S. Navy, worked odd jobs before becoming a literary celebrity, and had a deep admiration for working people evinced throughout his life and work. On the other hand, however, is a man with literary aspirations, someone seeking to be an artist while mixing with intellectuals and bohemians. It’s an environment in which it’s easy to imagine all of that workwear beginning to feel more affected than purely practical — a premonition, perhaps, of the throwback styles of the present day, all of which can trace a straight line back to Kerouac and company. 

Brenden Gallagher eloquently outlines these tensions inherent in Kerouac’s style, as well as the influence his clothing would have on generations to come:

‘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.’

This week would have marked Kerouac’s hundredth birthday. If it feels somehow improbable that he could have been born a century ago, you’re not alone in that feeling. I imagine it has something to do with his relatively untimely death or a longstanding association with youth culture — a connection that is itself likely to outlive us all.

For me, though, it’s definitely also linked to his clothes. Kerouac wore as a matter of course all of the things that every workwear-obsessed dresser (myself among them) has spent a great deal of time and effort trying to imitate. It’s no surprise, then, that all of it still looks as good as the day he first wore it. As Gallagher observes, it feels as though you could drop Jack on any city street in the present day and he’d fit right in. In this sense, Kerouac’s clothes have proven to be every bit as enduring as his writing has. If it feels like a safe bet to think that free-spirited teens will continue to read On the Road for years to come, it seems equally fair to say that they’ll also still want to dress like the man who wrote it.

---

* This post may contain affiliate links. If you buy something using them, we get a small percentage of the sale at no cost to you. More info at our affiliate policy.