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The Original Playboy

Black Chukka Boot

Black Chukka Boot

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.

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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.

Details:

  • 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.

Regular price £270.00 GBP
Regular price Sale price £270.00 GBP
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A HOLLYWOOD FAVOURITE. WORN BY LEGENDS.

The story of The Original Playboy shoes began in 1936 when English shoemaker Hutton in Northampton created a completely new shoe with a unique and patented crepe sole construction. The ‘Play-Boy’, as it was originally called. The construction was based on a thick 100% natural crepe sole attached to the upper, a signature piping sewn all around the shoe and an inch-high crepe foxing to complete the shoe.

An iconic, and timeless, classic that has since been worn by royalties, legendary Hollywood actors, jazz musicians, rockabillies, hip-hoppers and a host of other good people around the world. 

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