During the early 1940's, Playboy shoes were successfully exported to Australia, Canada, and the United States where they became synonymous with the Ivy League look which was soon to sweep the world, Steve McQueen, a long-time champion of the brand, can be seen wearing Playboy Chukka boots in his 1958 debut movie, The Blob.
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Bernard Rhodes (ex-Clash manager) Playboy's in 1977
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Back in the UK, Playboy shoes proved popular with the Teddy Boys from the early 1950's through to the 1960's, meanwhile, in the United States Miles Davis wore a pair of Chukka boots during the recording of his 1958 album ‘Milestones,’ as Steve McQueen continued to give the brand his support, wearing Playboy Chukkas in a 1963 photo spread for LIFE magazine and later in his 1968 movies Bullitt and The Thomas Crown Affair.
During the 70's Ebony magazine carried adverts for Playboy shoes in the US and later in the decade, Playboy's were later adopted by New York's early Hip-Hop movement of the 70's and early 80's as documented in the exhibition 'Urban Armor: Hip Hop's Fashionable Flavor,' curated by Rock Steady Crew member, choreographer and film director, George 'Popmaster' Pabon. At the same time, the emerging British Rockabilly's wore Playboy Chukka boots and shoes as part of their 'back to basics' style.
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