Size and fit

Great style knows no boundaries and the Vans Checkerboard is much the same way. The model is a unisex shoe and is available in men’s measurements. Women can convert to their size by subtracting one size and a half from their usual shoe measurement.

The shoe makes use of a traditional lace-closure system for fit adjustment and secure lockdown.

Vans Checkerboard Old Skool Style

Go flashy the old-school way. The Vans Checkerboard Old Skool is a funky shoe that just looks hip no matter how you style it. The sneaker particularly looks great with olive shades. One way women can wear the sneaker is to pair it with short denim overalls and a tank top in tonal shades of olive. Men can utilize the same green hue in their jeans and combine it with a black tee.

Notable Features

The coveted Vans checkerboard print has found a new home in the iconic Old Skool, resulting in a head-turning footwear that anyone would be proud to show off. This sharp-looking new style, however, is accompanied by the same trusty sturdiness, flexibility, and comfort of the Old Skool silhouette.

Vans Checkerboard Old Skool History

The Vans Checkerboard Old Skool is inspired by the legendary silhouette that has remained in production despite being released some forty-odd years ago. In 1977, the brand debuted the Old Skool, their first-ever model to feature the famous leather sidestripe that proclaims a shoe is unmistakably Vans.

The Old Skool had a hip style and was a favorite among skateboarders and everyone else who wanted to get away from the mainstream shoes of the time. The sneaker was made of suede and canvas and had reinforced toecaps. The design also had the happy coincidence of being ideal for unleashing creativity, and soon Vans Old Skool shoes with shades and doodles of all kinds were sprouting up, courtesy of their artistic owners.

Despite the decades that have passed since the icon’s release, it has remained as relevant as ever. One proof of this is the number of iterations and collabs that have come out based on the low-top’s silhouette. One example of which is this very retro-inspired Checkerboard Old Skool that combines the two of the best things that the brand is known for—the Old Skool silhouette and the checkerboard print that debuted on Style #48, or more commonly known as the Checkerboard Slip-On.

Nice to know

  • The Vans Checkerboard Old Skool features a suede material on the toecap, heel, and along the tongue for added durability while canvas covers most of the shoe’s upper.


How Vans Checkerboard Old Skool ranks compared to all other shoes
Top 7% sneakers
All sneakers
Top 14% Vans sneakers
All Vans sneakers
Top 6% low sneakers
All low sneakers


The current trend of Vans Checkerboard Old Skool.
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Danny McLoughlin
Danny McLoughlin

Danny is a sports nut with a particular interest in football and running. He loves to watch sports as much as he loves to play. Danny was lead researcher on RunRepeat and The PFA’s report into Racial Bias in Football Commentary. His football and running research has been featured in The Guardian, BBC, New York Times and Washington Post.