Step into a classic with the Original Playboy chukka boot, an iconic style originally crafted in 1936 England. Celebrated for its roots in menswear history and embraced by cultural icons like Steve McQueen and Miles Davis, this boot blends informal ease with a touch of sophistication. Its pivotal role in Ivy league fashion makes it a must-have for those who appreciate a transgressive edge and timeless style.
From the brand: 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
, favo
u
red by icons ranging from Hollywood’s Steve McQueen to music
al
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.
