David Carr, a journalistic titan in his own right, wrote the above quote following Hunter S. Thompson’s death in 2005. Though Carr clearly admired Thompson, he also clearly had his reservations about leaving behind the trademark loose ties and rolled up sleeves off of his fellow writers as gonzo writing led to gonzo fashion. Despite Carr’s cautious objections, it’s a safe bet that most writers today view Thompson’s trademark style as a moment of liberation for writers the world over.

With his bucket hat, Hawaiian shirt, aviators and short shorts, Thompson certainly had an unconventional look. That’s what made him a style icon. Dressing conventionally rarely leads to fashion immortality. Before him, the image of the eccentric male writer was generally expected to fit inside the confines of a suit coat. His tweed jacket might have the suede patches of a bohemian or stains from the chalk dust of a rigorous lecture (better to differentiate them from the straight-laced Wall Street crowd), but a dapper look was the default. Not only did Thompson’s gonzo style open up possibilities in terms of prose, it changed the way we think about what a writer looks like.

If you sift through images of Thompson’s contemporaries like Vonnegut, Irving, Pynchon, and Updike, you encounter one drab blazer or button-down after another. Thompson’s style wasn’t designed to fit into the hallowed halls of academia or look at home on the back of a book jacket. His look was designed for his office—the real world—and it was meant to both blend in and stand out.

Thompson dressed like a tourist in his own country. His signature Hawaiian shirt (often technically an Acapulco shirt, which is no less loud, despite the geographical chasm), aviators and bucket hat were the sort of thing he could wear to Hell’s Angels bars and Las Vegas diners without being looked at like he had just fallen out of an ivory tower. That isn’t to say he was incognito though; Thompson often accented his look with wild accessories. The writer even owned one shirt entirely made of fishing lures. On balance, his style reclaimed tired elements of Americana while also creating a style that feels at once hip and timeless.

Thompson’s style didn’t exist wholly in a void. From time to time he called on the fashion influences of his predecessors. In many ways, he followed the sartorial traditions of Ernest Hemingway and Jack London; he even wore safari jackets and pith helmets on his adventures from time to time. He didn’t wear these items to fit in with adventurers, soldiers and outdoorsmen like London and Hemingway once did. These pieces gave him an air of authenticity as he made his way through dingy dive bars and dens of psychedelia. Thompson too was dressing as a creature of the frontier. It’s just that frontier was often in his mind.

Setting aside his odd accessories, one of the reasons that Thompson’s style is so appealing is that it is so completely American. Hawaiian shirts, white Chuck Taylor All-Stars, and Ray-Ban Aviators accompanied by guns, cigarettes and liquor bottles. For better or worse, it’s hard to find to find a set of signifiers more U.S. of A. than that. If you were to put a collection of fashion pieces into a time capsule in an attempt to define 20th century men’s style, the result likely wouldn’t be far off from many of the items in Thompson’s wardrobe.

In his work, Thompson was challenging what an American journalist’s work should look like. As many students of the craft are quick to point out, the opening paragraph of Hell’s Angels: A Strange and Terrible Saga is as good a textbook example of “who, what, when, where, and why” as any. But, of course, he challenged the narrow definitions of these journalistic pillars in everything he wrote. No one before or since saw the Kentucky Derby or a campaign rally the same way he did. Thompson understood that objectivity is a construct, and that truth remains in the eye of the beholder, no matter how drug-addled they may be.

Hunter S. Thompson didn’t just challenge what writing should look like; he also challenged what a writer should look like. The classic authorial look of the blazer with patches and the pipe is the requisite look of the British man of letters. For centuries, American writers took their cues from this tradition. With his fashion choices, Thompson forged a new definition of writerly style.

This look resonated with Thompson’s contemporaries and has lived on in the culture for decades. When Johnny Depp starred as Raoul Duke in the 1998 film adaptation of Fear and Loathing in Las Vegas, he and director Terry Gilliam opted to put the actor in Thompson’s actual vintage wardrobe from the era. Films of that period, like Big Lebowski, also clearly count Thompson as a style influence. In the literary world, a new generation of writers, like David Foster Wallace, recognized that they didn’t have to wear the suits as long as they could write the books. By the turn of the century, it was clear that Thompson had won a new generation of artistic style.

Now, when young folk with literary aspirations seek to dress the part, they often dress like Thompson. Hawaiian shirts are a style staple of hipster neighborhoods populated by graduates of the Iowa Writers’ Workshop. Aviators and Chuck Taylors are as common in coffee shops as iced lattes. Last year, a Kickstarter aiming to reproduced Thompson’s iconic Safari jacket was fully funded.

High fashion too has nodded at Thompson’s outsized influence on the artist’s closet.
2017 collections from Tommy Hilfiger and No. 21 evoked Thompson’s signature looks. Pieces of Thompson’s wardrobe come back into style with each passing season. 2017 even saw an unexpected bucket hat renaissance. Even if you can’t point to a particular collection that explicitly evokes gonzo journalism-style, it’s hard not to spot an aloha shirt or bucket hat without the mind inevitably conjuring up images of Hunter S. Thompson (or, at the very least, Johnny Depp’s Raoul Duke)

The most important lesson for us to take from Thompson’s closet is not that a writer ought to be wearing Chuck Taylors instead of leather wing-tips or short shorts instead of a classy blazer. The takeaway should be that style, like art, can’t really be imitated. The true artist will draw upon their influences to build work all their own. The same is true of a man with real style.

If you try to dress like Hunter S. Thompson, you’re sure to fall short. But, if you think like Hunter S. Thompson when you dress, you might just take your look to that next gonzo level.