The Original Playboy

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.

AUTUMN/WINTER '24

Discover the John Simons Autumn/Winter Collection: a blend of Ivy League classics and modern craftsmanship, made for the season ahead. With thoughtfully selected pieces, warm layers, and versatile silhouettes, each piece is crafted to bring comfort and understated style from autumn through winter.

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Journal

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  • Customer Spotlight: Peter Robinson
    • Customer Spotlight

    Customer Spotlight: Peter Robinson

    In this Customer Spotlight, we explore the life and experiences of Peter Robinson, an esteemed photographer deeply connected to British fashion and style. Born in February 1944 and educated at...

    • Customer Spotlight

    Customer Spotlight: Peter Robinson

    In this Customer Spotlight, we explore the life and experiences of Peter Robinson, an esteemed photographer deeply connected to British fashion and style. Born in February 1944 and educated at...

  • Customer Spotlight: Aya Burns
    • Customer Spotlight

    Customer Spotlight: Aya Burns

    In this Customer Spotlight, we introduce Aya Burns—a designer whose deep appreciation for timeless style and quality craftsmanship shapes her every purchase and sartorial philosophy. Aya’s journey began as a...

    • Customer Spotlight

    Customer Spotlight: Aya Burns

    In this Customer Spotlight, we introduce Aya Burns—a designer whose deep appreciation for timeless style and quality craftsmanship shapes her every purchase and sartorial philosophy. Aya’s journey began as a...

  • The Original Playboy X Steve McQueen

    The Original Playboy X Steve McQueen

    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...

    The Original Playboy X Steve McQueen

    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...

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