
New to 2nd Academic : Original Playboy
The Original Playboy shoes distinct quality and appearance found them favoured amongst Jazz musicians, Hollywood royalty and many other icons of subculture since the brand's inception in 1936. Its rich history and iconic silhouettes make a perfect fit for 2nd Academic and we are excited to be carrying our favoured selection for Spring ’25.

A 100% natural crepe sole was a distinguishing feature of the first ‘Play-boy’ design which was patented in by a shoemaker named 'Hutton' in Northampton in the mid 1930s. They were originally made for town and country wear and were marketed with the tagline ‘The easiest shoe on earth’ due to their simplicity. In time, they found their way onto golf courses, football pitches and even the sands of Cairo during WW2 where the Eighth Army placed their preference with Play-Boys over the later-famed desert boot.

In subsequent decades Hollywood icons like Steve McQueen and Marlon Brando were known for sporting Play-Boys, underscoring their place in a golden era of style. The Play-Boy chukkas were touted as McQueen’s favourite boots. In 2024, a special edition of the boot was launched as a homage to the the ‘King of Cool’ who wore them both privately and on film.

As Ivy League style and the sound of Jazz prevailed in the 1960s, so too did the Play-Boy. Miles Davis was another loyal fan, they can be spotted in many of the images of him cradling his trumpet or nursing a cigarette from this era and also on the inner artwork of his masterpiece 'Kind of Blue.'
Up until the turn of the millennium, the popularity of the classic Play-Boy styles continued with the likes of Mods, Rockers and in Hip Hop style. It was around this time that the brand expanded their product range to include Loafers and Two-tone variations.

Years of stylistic excellence exists in the DNA of the Original Playboy brand, who now make their shoes in Portugal. Though many things have changed culturally since their inception, their merit as a manufacturer of stylish and hardwearing footwear has not. Shop our selection here.