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The Original Playboy

Black Chukka Shoe

Black Chukka Shoe

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 £250.00 GBP
Regular price Sale price £250.00 GBP
Sale Sold out
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PARABOOT

Here at John Simons we are proud to stock Paraboot, an iconic French brand with whom we have worked with since 1984, making us the oldest stockist in the UK.

Founded by Remy Richard in the Alpine French town of Izeaux in the early 20th Century, the Paraboot brand as we know it today was born from one of Richard’s earliest visits to the USA. In 1926, Richard arrived in the USA during a boom in the rubber industry and was confronted with a new style of work boot with heavy rubber soles. This style of footwear differed greatly from the refined leather-soled shoes Richard had produced previously and served as the impetus for a new style of footwear.

In 1927, Richard founded Paraboot, a brand with a distinct focus on rubber-soled footwear, appropriate for heavy labour. The brand’s name was a combination of the words “Para”, the town in Amazonia from whence the rubber came, and “Boot”, a nod to the American-style of footwear Richard had encountered on his travels.

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