Play your own game, be your own man, and don’t ask anybody for a stamp of approval.
—Hunter S. Thompson, Fear & Loathing in America, 1971
Hunter S. Thompson’s sizable persona—his essential joy-stalking soul, his delirious inimitability, and his forging, uncompromising texts—not only magnetized those he met, but has also fascinated and charmed kindred spirits the world over. The Hunter style and substance fueled not just a new way of first-person, subjectively written journalism. His approach to life and what he wore while living it has also become the stuff of legend.
Thompson reveled in his fun-filled life and had an equally screwball sartorial nature. Day to day, the six-foot-three Thompson’s dress sense was more of a uniform—a uniform in which to attack and chase the day. Dark aviator shades, a khaki safari suit jacket, bold Hawaiian shirts, Converse sneakers, and very short shorts were typical Thompson wardrobe staples. The flourish of his clothes, cowboy hat, cigarette holder, and knee-high socks were as off the wall and unexpected as his performances in life with firearms: he very often autographed his books by shooting them with a gun.
Getty Images: Ochs, Michael
Hunter S. Thompson at his ranch near Aspen, Colorado, mid-1970s.
Getty Images: Felver, Chris
Hunter S. Thompson on the road, 1990.
As a freethinking radical, Thompson personified an outsider looking in on both counterculture and the mainstream. His sardonic and squinted view of the sixties and seventies has become synonymous with the eras. He covered Nixon’s election, the Watergate scandal, and the Vietnam War; he wrote about hippies and the demise of the beatnik generation. In 1966 he published his first book, Hell’s Angels: A Strange and Terrible Saga. Like his second book, Fear and Loathing in Las Vegas, his piece began as a feature for The Nation magazine, and after it appeared, Thompson was offered a deal to write something longer. He spent the next year living with and observing the Hells Angels he had met, and wrote afterward in the work: “I was no longer sure whether I was doing research on the Hells Angels or being slowly absorbed by them.” He had spent time as a teenager typing up F. Scott Fitzgerald and Ernest Hemingway, in order to pick up the rhyme and reason of the greats, but while he was working on Hell’s Angels, Thompson’s unique style of writing kicked in. In his 2003 memoir, Kingdom of Fear, Thompson says he fit into a new lineage of author: “I wasn’t trying to be an outlaw writer. I never heard of that term; somebody else made it up. But we were all outside the law: Kerouac, Miller, Burroughs, Ginsberg, Kesey; I didn’t have a gauge as to who was the worst outlaw. I just recognized allies: my people.”
Thompson owned a rescued coatimundi called Ace who learned to use the toilet and liked to play with soap.
One of Thompson’s favorite books was One Flew Over the Cuckoo’s Nest by Ken Kesey.
Thompson planned his own funeral and, before committing suicide in 2005, left a memo saying that his ashes should be launched into the sky via firework shells from the top of a clenched-fist monument he designed himself. The red, white, and blue blast can be seen on YouTube.
During the 1970s, Thompson often wore a combination of some of the following: very short shorts and sports socks, Converse All Stars, safari or bush hats, visors, aviator sunglasses, Hawaiian shirts, leather bracelets, and shark’s-tooth necklaces, along with a cigarette holder and a gun as accessories. The fashion industry has embraced these sartorial distinctions. Every so often, Thompson-style Gonzo gear emerges as a catwalk reference, with Vogue urging its readers to “embrace your inner Hunter.” Designers harvest his style—in its 2016 spring collection, the British street wear label House of Holland dressed its models in Thompson’s signature separates. Although it seems ludicrous that the identity of a Taser-toting bald guy should have sartorial sway in the twenty-first century, his uncoordinated clothing choices have nevertheless become criteria of cool.
California, Labor Day weekend . . . early, with ocean fog still in the streets, outlaw motorcyclists wearing chains, shades and greasy Levis roll out from damp garages, all-night diners and cast-off one-night pads in Frisco, Hollywood, Berdoo and East Oakland, heading for the Monterey peninsula, north of Big Sur . . . The Menace is loose again, the Hell’s Angels, the hundred-carat headline, running fast and loud on the early morning freeway, low in the saddle, nobody smiles, jamming crazy through traffic and ninety miles an hour down the center stripe, missing by inches . . . like Genghis Khan on an iron horse, a monster steed with a fiery anus, flat out through the eye of a beer can and up your daughter’s leg with no quarter asked and none given; show the squares some class, give em a whiff of those kicks they’ll never know . . . .
—Hunter S. Thompson, Hell’s Angels, 1966
Everybody is looking for someone who can stand up in the wind. It is lonely standing up and crowded lying down. I refuse to be an anchor for other people’s dreams—but then I refuse to anchor mine to anyone else. So I have no choice but to stand up and piss into the wind.
—Hunter S. Thompson, The Proud Highway, 1994