“They’re always comfortable, clean-looking work boots." ...

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 ...

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 ...

Supreme and Timberland teams up once again for this time a new version of their signature waterproof Chukka boot. Coming in three different colorways (navy, red and camel), the exclusive boots have ...

Like all things in life, not all Timberland boots are made equal. Some pairs are seasonal hits, some make brief cameos over fashion week, and some disappear into the ether after a year or two. But ...

Timberland is no stranger to limited-edition collections, and its latest release is one you’re not going to want to miss out on. Retailing for $150 and $180, respectively, the collection includes a ...

You can wear a chukka boot in the fall. In the winter. In the spring. Hell, you can wear it in the summer, I guess, but we're not worried about that right now. Should you believe that a chukka or ...