Original Playboy

Chukka Boot – Black


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.

Crafted from the finest suede and available in classic rich brown and black colourways, step into the world of lieutenant Frank Bullitt with this iconic piece of footwear.


Hand lasted construction
Water resistant hunting suede
Two eyelet style
Natural crepe sole


We recommend pairing the Playboys with a pair of our Ivy League trousers, and an Ivy League jacket for a look which would make Steve himself proud.