Published October 9, 2026

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Updated October 9, 2026

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The chukka’s origins trace back to British polo players in India during the early 20th century (its name comes from the word “chukker,” referring to a period of play). But the ankle-high boots eventually found their way into military circles, where British soldiers stationed in North Africa during World War II favored lightweight suede versions for their comfort and practicality. 

After the war, Nathan Clark took inspiration from these boots to create the now-iconic Clarks Desert Boot in 1950, helping bring the style into the mainstream. By the ’60s, chukkas had become a favorite among everyone from British Mods to Steve McQueen, cementing their place as one of menswear’s most enduring silhouettes.

This past summer, Vans took its own crack at the style, debuting a Half Cab-looking silhouette with an overall shape and lacing system borrowed from the chukka. However, launching in black and white colorways, the sneakers still looked like Vans at the end of the day.

That’s all reconciled with the latest expansion of the series. Now, the OTW Chukka 49 Vibram is getting the heritage-looking variants it deserved the first time around.

Part of Vans’s more experimental Off the Wall label, the Chukka 49 has now dropped in three new colorways that appear way more fitting for a shoe bearing the “chukka” name: Vintage Cocoa, Oil Green and Dress Blue. 

Still featuring a premium suede upper with a leather strip at the heel, the overall aesthetic now just feels more classic. Notably, the brown Vintage Cocoa looks like a direct successor to the original Clarks Desert Boot. Meanwhile, the blue and green colorways provide warm, versatile alternatives that still don’t look too casual. 

The only thing missing from these variants is gum rubber midsoles. Instead, the base lands in black (replacing the white bases from the previous release) with the brand’s signature foxing tape around the midsoles. Adding a nice touch, there’s a tan ring at the top of the sole, which happens to match the tan laces that ship with the shoes.

As the name suggests, these sneakers also get custom Vibram outsoles, making them far more capable than your average chukka boots (or skate shoes, for that matter).

The new OTW Chukka 49 Vibram colorways are now available from Vans’s website. Just like the first drop, these are priced at $110 each.

About the Author: Ethan Brehm is an associate editor at Gear Patrol writing about footwear, watches, spirits, EDC and more. When he’s not shopping for his next G-Shock, he spends his time watching movies and planning a future road trip with his family. He firmly believes CDs sound better than vinyl.