John Simons are proud to reintroduce a renowned mid-century style back into our stock, in the form of the Original Playboy chukka boot.

Originating in 1936 England, the Playboy chukka has left an indelible mark on the landscape of menswear, favoured by icons ranging from Hollywood’s Steve McQueen to musical legends such as Miles Davis. With its association to music, action and the informal elements of the style, the Playboy boot has become a symbol of the more transgressive edge of Ivy league dress since their inception.