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Hunter S. Thompson’s Endless Trip

The dark prince of gonzo journalism, Thompson dressed with memorable flair, from the cigarette holder to the Aussie hat and Hawaiian shirts. Here’s how to do it.

Paul Harris/Liaison

Hunter S. Thompson’s drug-and-alcohol-fueled journalism inspired several generations of aspiring authors, hell raisers, and more than a few garden variety drug lovers. Not even his biggest detractors would deny that Thompson left a big footprint on American letters.

But Hunter S. Thompson as a fashion plate? Really?

Apparently so. Thompson’s aviators-and-bucket-cap look, which he made famous with the simple tactic of wearing that combo everywhere, has become an established marker of countercultural wannabe cool. (OK, in the cool category, it absolutely doesn’t hurt to be played by both Johnny Depp and Bill Murray when movies are made of your exploits.)

It’s a look that has been repeatedly copied, most recently by a Thompson-inspired clothing startup seeking Kickstarter cash to reproduce the Godfather of Gonzo’s Abercrombie & Fitch patchwork hunting coat.

So you can’t write like Thompson, and you certainly can’t match him pill for pill or shot for shot (unless you want to end up in the ER before lunch). But you can dress like him. Here’s how.

The Hawaiian shirt. Johnny Depp famously borrowed some of HST’s own floral button downs for Fear and Loathing, many of which were as loud as the man himself. Lucky for you, the Hawaiian look is having a moment this summer, meaning there are loads of options. For good options, check out Patagonia, J. Crew, Mr. Porter, and, naturally, Tommy Bahama, who’s linen version will keep you as cool as you look.

The sunglasses. Mandatory for blocking both UV rays and eye contact, Hunter was fond of Ray Ban’s Shooter Aviators, specifically the now-discontinued Kalichrome “Bullet Hole” model. Lucky for you, we have eBay. Just bear in mind that the signature yellow lenses aren’t going to help a whole lot at the beach.

The polo shirt. Alongside shooting guns and getting wasted, Hunter loved to play golf. Actually, he famously loved to do all three at once. He also loved the classic, clean look of white polo shirts, particularly the classic LaCoste pique polo.

The khaki shorts. Remember, things were a little different back in Thompson’s day. Meaning, you may have a hard time finding shorts as short quite as, errr, snug as his. That said, Ralph Lauren’s flat front chino shorts are a close, somewhat modernized approximation that won’t stretch your self confidence to kick it in as you throw back Wild Turkey by the pool. For true accuracy, don’t forget the socks, white, pulled up as high as he was.

The shoes. This one’s simple: check almost any picture of Thompson, whether by the beach or in a tux, and he’s rocking a pair of white Converse Chuck Taylor All Stars. He wore them so much, in fact, that his widow told Radar that there are still some 70 pairs kicking around their house. We suggest stepping this up ever-so-slightly and opting for the new Chuck II, which looks almost the same but has a much improved level of comfort and support over the infamously foot-thrashing originals.

The hat. This one’s easy. Thompson long favored the classic white Tilly T3 Snap Up hat, so much so that his wife made sure to put it on his head before he was cremated.

The camo pants. What goes better with a passion for high powered firearms than a pair of camouflage pants? There are plenty of options out there from the fashion industry, but if you’re gonna go camo, at least be authentic about it and get yours from a military surplus shop.

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Still set on that hunting coat? Well, forget the imitations and at the very least get the original, now-vintage and ultra-rare Abercrombie & Fitch model. Fair warning, though: you may have to cut down on your daily drug intake to save up for the sobering $5,000 price tag. Oh, but lose the cigarette holder. Seriously.