Original Playboy

The inception of The Original Playboy shoes dates back to 1936, when Hutton, an English shoemaker based in Northampton, developed an innovative shoe featuring a distinctive and patented crepe sole construction. Initially named the 'Play-Boy,' this design incorporated a thick, 100% natural crepe sole affixed to the upper, complemented by signature piping encircling the shoe and an inch-high crepe foxing. Marketed as "The easiest shoe on earth," it was intended for golf and casual wear. By the 1950s, notable figures such as Miles Davis, Steve McQueen and Marlon Brando were seen sporting the Original Playboys. The 1960s marked a significant shift for the brand, as Playboy shoes and Chukkas became emblematic of the American Ivy League aesthetic.