Dover Street Market

Beloved by skaters and sneakerheads alike, Vans kicks come with distinctive silhouettes that haven’t changed much over the years. But while its archive has more or less remained the same when it comes to shapes, the Californian brand has released countless colorways over the years, and none are more iconic than the interpretations of its signature checkerboard print.

First seen in the late ’70s, the checkerboard colorway was actually introduced by Steve Van Doren (son of Vans founder Paul Van Doren), after noticing that skater kids were coloring their shoes’ midsoles to look like a checkerboard.

Soon after the pattern was applied on Vans canvas Slip-Ons, the checkerboard iteration gained mainstream popularity, further supported by cosigns from Sean Penn. In the early ’80s, the Vans checkerboard became a favorite among subcultures, too, with Ska adopting the checkerboard as one of their symbols to represent unity and the breaking of racial barriers.

Though the checkerboard pattern may have lost its Ska essence now, the colorway remains a huge hit, with Vans including OG checkerboard in its most recent general releases and elevating the classic in interesting new collaborations. Now, in appreciation of the timeless design, we’ve picked some of our favorite interpretations of the Vans checkerboard currently available, from classics to wavy modern takes.

And while the classics will come as affordable grails, slightly elevated highlights come from Dover Street Market and END.‘s spins on the classic pattern, along with more fashion-forward versions from the recent Ponyhair pack and waterproof GORE-TEX Sk8-His.

View all our favorites below.

Classic Slip On Sneaker

Vans

$50

Checker Flame Slip-On

Vans

$55

Checker Flame Authentic

Vans

$55

Checker Flame Sk8-Hi

Vans

$59

US Open Old Skool

Vans

$65

Surf Check Sk8-Hi 139 Decon SF

Vans

$65

Vans

Vans Vault x DSM

$74

Vans OG Slip On

END. x Vans

$69

Comfy Cush Era LX

Vans Vault

$109

Pony Hair Slip-On Cap LX

Vans Vault

$72

Pony Hair Sk8-Hi Cap LX

Vans Vault

$200

SK8-Hi Gore-Tex LX

Vans Vault

$225

If you want a deeper dive into Vans, watch the video below.

To stay up to date with more Shopping content from Highsnobiety, follow @Highsnobietyshopping on Instagram and @Highsnobdrops on Twitter.

Our designated shopping section features products that we love and want to share with you. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

Shopping Writer
What To Read Next