The most recognizable chukka style is, of course, the desert boot. The desert boot is typically made with a soft suede. A ...

As the weather cools down and the first signs of fall arrive, it’s time to swap your summer shoes for something more rugged, warm, and weather-ready. And if you’re looking to upgrade your footwear ...

For those guys who want the durability of a work boot and the look of a chukka, Stussy and Timberland have come up with a hybrid that combines the best of both. The 4-eye chukka—available in black and ...

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Taking a more minimal approach compared to their recent project with Dr. Martens, Stussy work up a new collaboration alongside Timberland on a pair of 7-eyelet chukka boot. Done up in a natural Brown ...

First released in 1973, Timberland's iconic yellow boot get what may be its most refined makeover in half a century.

Bape is back with another solid footwear collaboration. After teaming up with the likes of Dr. Martens and Havaianas this summer, the iconic streetwear brand has connected with Timberland on a ...

Spotted on the likes of Kanye West, Cara Delevigne, Drake, J Lo and a whole host of other A-listers, Timberland has well and truly cemented itself within the cool kid scene. And no with Black Friday ...