Hunter S. Thompson was hardly a style icon in the traditional sense. His freewheeling, individualistic, violent and drug-heavy lifestyle amounted to something of a definitive statement against fashion and all the codes and conventions it might represent. But he was an expert at crafting his own image, using clothing and accessories to brand himself an outsider, a counter-cultural hero. Like his rebel forebears James Dean and Steve McQueen, he created his own brand of cool. Here, the essentials.


The Hawaiian Shirt
For Johnny Depp's performance as Raoul Duke in the movie version of Fear and Loathing in Las Vegas, the actor borrowed his Hawaiian shirts from Thompson himself. Set your sights for spring 2011 on the neat, floral shirts from this June’s D&G menswear show. Bag of groceries (pictured) optional.

The Shades
The dual function of sunglasses—they not only shield eyes but also mask the severity of hangovers—made them a must in Thompson’s getup. We recommend classic Ray Ban aviators, in a semi-opaque tint. “I like the way that sunglasses look, but I seldom wear really dark sunglasses,” Thompson told Playboy’s Tim Mohr in 2005 (for his last interview). “I’ve found that if people can see my eyes through the lenses it’s more comfortable. I try not to have my costume be a problem for me or other people.”

The Chucks
Thompson’s dedication to Converse Chuck Taylor sneakers was obsessive and lifelong. His widow Anita Thompson told Radar in 2008 (when Thompson was posthumously featured in an advertising campaign for the brand) that he had worn them daily since the 1960s, and that there are still over 70 pairs left in their house.

The Wild Cards
Though Thompson had a preference for practical, his obsession with the decay of the American dream infused his outfits with a sarcastic twist. He threw together clothes with no concern for idiom, fit or occasion, pairing sneakers with tuxedos and favoring loud prints and very short shorts. Thompson would certainly have appreciated the wry pomp of Thom Browne's fish-print shorts suits for next spring—he himself owned a shirt completely made from silver minnow fishing lures.