There’s a lot more history, geography, and, well, swagger, pieced into the simple design of a Clarks Desert Boot than first greets the eye. Its trademark stitchdown profile, in fact, traces a veritable timeline of modern cool, snaking from the South African veldt, through the souks of Cairo, and touching Kashmir, London, and Chicago before ultimately finding its chosen home in the streets of downtown Kingston, Jamaica.

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Photo © George Williams / Greensleeves Archive

To make a centuries-long story short, Nathan Clark, great-grandson of company founder James Clark, based his design on the footwear of British soldiers stationed in Lahore en route to fight the Japanese in Burma circa 1941: breathable but rugged safari boots requisitioned in Cairo’s Khan el-Khalili bazaar for Britain’s Eighth Army during the North African campaign of World War II. That Anglo-Egyptian design was itself a particularly elegant take on a unique Dutch–South African hybrid called the vellie (short for veldskoen, literally “field shoe”), common in the region since the 1700s at least.

Photo © George Williams / Greensleeves Archive

In spite of that durable pedigree, however, Clark was told the design would “never sell,” and the initial response in the U.K. seemed to confirm that diagnosis. Desert Boots did not take off, in fact, until they found a stateside market via Chicago’s Shoe Fair in 1949. That whiff of American cool, perhaps combined with the minimalism of its form-follows-function design, is what made Desert Boots de rigueur footwear for the mods who rewrote the stylebook of Britain’s postwar boom. Steve McQueen burnished the badman credentials of desert boots even further with his choice of mod footwear on- and offscreen—although to this day, controversy rages among McQueen obsessives as to whether the brown suede vellies glimpsed in his iconic 1968 action film Bullitt were British- or Italian-made.

Photo © Beth Lesser / Courtesy One Love Books

By that time, the Desert Boot’s particular cocktail of dapper British gentility and commando roughness—not to mention its practicality in an urban, tropical milieu—had made Clarks irresistible to the rudeboys of Kingston’s burgeoning concrete jungle. The West Indies was such a key secondary market for Clarks, in fact, that at one point the Desert Boot was redesigned with a longer, narrow toe specifically to cater to the Caribbean sense of style (possibly an echo of the Jamaican predilection for pointy-toed “roach-killer” cowboy boots). Traditionalists prevailed and the original, more rounded toe was eventually reinstated. But the Clarks shoe and a certain gunslinger lifestyle became so synonymous, in fact, that by the late ’60s the infamous Jamaican police enforcer, superintendent Joe Williams, was known to raid the outdoor dances regularly held by Sir Coxsone Dodd’s legendary reggae sound system in his jurisdiction on Kingston’s Spanish Town Road and divvy up the crowd into Clarks and non-Clarks segments, so as to separate the rudeboys from all nice and decent people. (The main outcome of all this, of course, was that it resulted in a minor epidemic of barefoot toughs and piles of hastily discarded boots).

As with many illicit affairs, official censure only heightened the passion of Clarks collectors in Jamaica. When Clarks introduced the Wallabee (a boxier, moccasin-inspired version of the suede chukka) in 1967 and the Desert Trek (a center-stitched hiking shoe, instantly rechristened as “bankrobbers” in Jamaica) in 1971, they practically flew off the stockists’ shelves straight onto the album covers of reggae’s most influential singers and DJs, dreadlocked Rastas and razor-trimmed lyrical gangsters alike. (Note the cover of dancehall pioneer’s Dennis Alcapone’s 1971 LP, Guns Don’t Argue, whereon Wallabees add a modish accent to a trenchcoat and Borsalino—not to mention machine guns—straight out of the Prohibition era of organized crime.)

Photo: Courtesy of Studio One

In the ’80s, the trend shifted from album-cover accessories to song lyrics and even titles (see Little John’s “Clarks Booty”), a high point of Clarks fetishism that coincided with the evolution of reggae into dancehall—and marked some of the genre’s all-time classics, like Super Cat’s “Trash And Ready” and Eek-A-Mouse’s “Wa-Do-Dem.” The era is lovingly documented in a new Greensleeves Records compilation titled simply Clarks in Jamaica and designed as a soundtrack to historian Al Fingers’s book of the same name. Fingers’s book is a visual bible of the phenomenon, chock-full of both priceless cultural lore and arresting photographs of reggae’s cultural heroes posed in an array of Clarks footwear, from Wallabees to discontinued variations like the Lugger and the Desert Mali. It moved northward as well, profoundly influencing a young subculture called hip-hop as Brooklyn Jamaicans made Wallabees and the similar silhouette of British Walkers a staple part of the b-boy uniform in New York City. Although Clarks’s star had dimmed somewhat by the ’90s, its cult status was kept alive by the unlikeliest of musical champions, including the mod revivalist devotion to the original Desert Boot exhibited by Liam Gallagher of Oasis, not to mention Wu-Tang Clan’s Ghostface Killah, aka the Wally Champ, who channeled his unrequited love for the ’80s Jamaica-to-Brooklyn look into a rainbow of hand-dyed colorways.

Photo: Jamel Shabazz / Getty Images

It took dancehall reggae’s reigning king Vybz Kartel to transform that die-hard cult following into a viral feeding frenzy (a craze that has helped push the shoemaker’s bottom line over the £100 million mark) when his young protégé Popcaan asked him with breathless admiration, “Whe’ you get yuh new Clarks deh, Daddy?” on a record in 2010. But by the time dancehall DJ Assassin proclaimed himself “Bad from Desert Clarks and diamond socks” in 2007, Jamaica had long since imbued the suede chukka, pants cuffed to expose argyle hosiery, the OG status that a pin-striped, double-breasted suit had for prewar dandies—a timeless, endlessly re-inventable signifier of dashing badassery.