We have men's chukka boots for every occasion. Our men's boots are crafted with high-quality materials using modern technology for durability and comfort. Look for a moc-toe chukka, or stick to a Chelsea boot-inspired design. Finish the look with a pair of our pants or chinos for a tailored but casual look.

From the supportive rubber soles to pliable but durable leather, these are ankle boots that you won't be afraid to wear all day. Grab a cap-toe style with a larger toe box for maximum wiggle room. A cushioned footbed will make you feel like you're walking on a cloud, even after hours on your feet. Whether you need them as a dress boot or a pair of shoes for the streets of New York City, you'll be able to walk with comfortable confidence.

We've engineered our chukka boots to take on just about anything. From reinforced eyelets, which resist the wear and tear of daily off-and-on, to ultra-grip soles designed for rough terrain, our men's shoes are made to keep going as long as you can. Plus, they help keep the planet going too. Our eco-conscious shoes use recycled, post-consumer, and sustainable material, to lessen our impact on the environment.

From a casual chukka boot to our best chukka boots to dress up, you're getting some of our favorite dress boots with every pair. Our chukkas are perfect to slip on in the city for a night on the town. We’ve paid attention to every detail, from the lacing to the suede exterior, and these boots can't be beaten for looks. Make sure to take a look at our new arrivals before you check out – we always have new styles coming in.