When is a chukka more than just a chukka? When it’s a Playboy. No, not that Playboy, I’m talking about the chunky-soled ankle boots that became legendary thanks to that other playboy, Steve McQueen. During his sixties heyday, McQueen was inescapable both on-screen and off, and when he was snapped lounging by the California coast, or jetting around town with whatever starlet he was seeing that week, he was oft wearing a hefty pair of chocolate suede chukkas with a big ol’ crepe sole.
Like a desert boot on a jacked up sole, Playboys were forever tied to McQueen’s style, but they never quite caught on here in America. Recently though, as the refined yet casual look of English footwear has caught on here in post-aughts America, Playboys have been steadily growing in popularity.
While Northampton shoemakers like Sanders have produced Playboys for decades, it was Mark McNairy who really made the boots accessible stateside by offering them as part of his New Amsterdam line. This once elusive boot is now just a few clicks away and if you’re wondering just how versatile such a thick-soled shoe can be, well I’ll let these photos of the King of Cool handle that one. —JG