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The Original Playboy

Dark Brown Chukka Boot

Dark Brown 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
Sale Sold out
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THE JOHN SIMONS KNITWEAR COLLECTION

Skilfully knitted in Scotland, our new knitwear range is going to keep you toasty in style this Autumn/Winter. Each garment has been hand linked, which involves carefully joining each piece of the sweater by hand which results in a seamless finish that enhances durability and comfort while allowing for greater flexibility and shape retention.

Shop our knitwear range to stay warm wearing our Ivy League staples.

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