Vans Checkerboard: The Only Guide You Need

Some prints belong to a decade. The Checkerboard spans them all.

It’s been on skate decks and cinema screens, in punk clubs and fashion weeks, on battered skate parks and high-fashion runways. More than four decades after the print appeared, those black-and-white squares are still a style icon.

And they’ve got some pretty cool history too, everything from a teenage bookmaker called Dutch the Clutch to Sean Penn and even a White House dinner.

Which is probably as good a reason as any to start at the beginning.
 

The history of the Vans Checkerboard print

Before checkerboard, before the Slip-On and before Vans was even Vans, there was Paul Van Doren.

In 1944, Van Doren had left school and was spending enough time at the racetrack to earn the nickname “Dutch the Clutch”, thanks to a talent for bookmaking and making money. His mother eventually put a stop to that and sent him to work at Randy’s, a shoe factory in Boston. He stayed in the footwear business for the next two decades.

By 1966, Paul, his brother Jim and partners Gordy Lee and Serge D’Elia had opened the Van Doren Rubber Company at 704 East Broadway in Anaheim, California. The idea was unusual: make the shoes on-site, then sell them directly to the people who would wear them.

Twelve customers bought shoes on opening day.

Within the first week, another customer asked for a colour Vans didn’t stock. Rather than saying no, Van Doren told her to bring in the fabric she wanted. Vans’ long relationship with customisation had begun. 

But the checkerboard itself only arrived about a decade later.

Steve Van Doren noticed teenage skaters colouring the midsoles of their shoes in checkerboard patterns. Vans took the DIY idea and moved it onto the canvas upper of the Slip-On. 

The squares stuck.

Vans Checkerboard and popular culture

The timing was perfect.

While checkerboard Vans were taking hold in California skate culture, Britain was experiencing the rise of two-tone ska. Bands including The Specials used black-and-white checks as a symbol of unity, and checkerboard footwear became part of the look around the scene.

Back in California, Vans was becoming harder to separate from skateboarding itself. The Old Skool had arrived, Stacy Peralta had made his mark and “Off The Wall” was becoming more than something written on a shoe box.
Then came Spicoli.

In 1982, Sean Penn starred in Fast Times at Ridgemont High playing Jeff Spicoli in black-and-white checkerboard Slip-Ons. The shoes even made the soundtrack cover. Sales took off, and something that had grown out of a Southern California skate scene suddenly had an international audience.

More kept coming.

Kristen Stewart wore checkerboard Slip-Ons when she was honoured on the Hollywood Walk of Fame in 2011. In 2017, singer-songwriter Frank Ocean paired his with a blue suit at a White House state dinner. Asked about the choice, his explanation amounted to not overthinking things,which feels right for a shoe you can put on without even tying a lace.

And checkerboard hasn’t stopped moving. Emily Ratajkowski and Gigi Hadid helped put the classic Slip-On back into the street-style conversation in the mid-2020s, while the shoes also started reappearing around fashion week.

At the other end of the fashion spectrum, Valentino has even reworked Vans checkerboard through its own VLogo as part of its collaborations with the brand.
 

What is Vans Checkerboard Day?

Checkerboard eventually became bigger than something Vans printed on shoes.

Launched in 2019, Vans’ Checkerboard initiative uses creativity as a way to support worthy communities and organisations. Through the Vans Checkerboard Fund, the brand has donated more than $10 million to organisations working across areas including creative access, mental-health support and inclusive community programmes.

Checkerboard Day has brought that idea to life through creative projects, workshops and community events around the world.

Want to get involved? Keep an eye on Vans channels and local events around Checkerboard Day, join a community project – or take the idea closer to home and make something yourself.

Draw. Paint. Skate. Photograph. Customise a pair of shoes. Make it your own.

Vans Checkerboard Slip-On: the original

Vans Checkerboard Slip-On: the original

If you want the checkerboard in its purest form, this is it.

The classic Vans Checkerboard Slip-On keeps things at their cleanest: canvas, elastic sides, waffle sole, no laces and a lot of little squares.

It works because there isn’t much else going on. Jeans, shorts, chinos, skirts, dresses – the checkerboard does the work—whether the shoes are half destroyed or fresh out of the box.

Vans Old Skool Checkerboard: a classic reimagined 

Want your squares with laces?

The Old Skool adds checkerboard to another Vans icon. The silhouette first appeared in 1977 and became the first Vans shoe to feature the now-famous Sidestripe.

Whether you’re wearing baggy denim, cargos, workwear trousers or long shorts, Checkerboard Vans Old Skool do the work.

Checkerboard Vans styles for women

There’s no particular trick to wearing checkerboard Vans women's styles. Just put them on and go.

Try Slip-Ons with loose jeans and a tank. Old Skools with a midi skirt. Authentics with tailoring. Or wear women's checkerboard Vans with a dress that seemingly has absolutely nothing to do with skate shoes.

Black and white is the obvious starting point, but checkerboard moves into different colours, scales and remixes, too. Treat the classic version almost like a neutral; treat brighter checks as the loud part.

Vans Checkerboard backpacks and accessories

Want to build in the print higher up?

A Vans Checkerboard backpack is an easy way to bring in the vibe. But it can also show up on shorts, caps, accessories and other pieces depending on the season.

How to style your Vans Checkerboard

The easiest formula? Black jeans, white tee and checkerboard Slip-Ons. 

For something more skate-led, try loose denim or long jorts, a boxy graphic tee and Vans Old Skool Checkerboard shoes. Add crew socks if you want to push the proportions.

Want it cleaner? Put checkerboard Vans with tailored trousers, a knit polo, an oversized blazer or a simple coat. 

Or ignore all of that and clash it with another print.

Checkerboard has already been through racetracks, ska clubs, skate parks, Hollywood, the White House and high fashion.

Now, make it your own.