The 1950’s saw the Playboy adopted by early British Teddy Boys and Ivy League types, Steve McQueen adopted the Playboy Chukka boot as his favoured item of footwear, wearing them as early as 1956 in the stage production of A Hatful of Rain as well as on film from 1958’s The Blob right through to Bullitt and The Thomas Crown Affair both in 1968, Playboy’s original Chukka boots were also his preferred daily wear during this period. Jazz legend Miles Davis wore Playboys for his 1958 Milestones album cover photo session.