Reviving mid-century fashion, the Original Playboy chukka boot is a timeless piece that blends style and versatility. First introduced in 1936, this boot has graced the feet of icons like Steve McQueen and Miles Davis, symbolizing a unique blend of music and casual elegance. Its chukka design offers comfort and rebellion, making it a versatile addition to any wardrobe. Experience a classic piece of menswear that elevates any outfit effortlessly.
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.
