Our men's chukka boots fuse serious style with everyday practicality. These men's boots are designed and crafted using premium materials, such as high-rebound foam made from natural materials, rubber outsoles, and premium leather from gold and silver rated tanneries. They are durable and functional and look great no matter the occasion, especially when paired with a set of stylish Timberland men's pants.

Men's chukkas provide all-day comfort whether you're at the office, exploring the city, or catching up with friends. Their GreenStride™ comfort sole and EVA-blend foam provide cushioning, while their Better Leather materials promise supple flexibility and softness so they can bend and flex with your foot. Better yet, all Timberland® chukkas are made with the environment in mind, ensuring the biggest footprint you leave behind with these shoes is that you leave on the beach.

By creating collections, we know we have an impact on the environment. That's why we don't just source recycled and sustainable materials, but build our chukkas to last. They come with reinforced eyelets, ultra-grip soles that won't wear down at the first sign of gravel, and hardy premium leather that will withstand time and elements alike.

Chukka boots come in an array of styles to suit every occasion. There are dressy styles for the office and casual styles for the weekend. There are even active chukkas for easy hikes and tracks. Each pair is designed with versatility in mind, so a single set of men's chukkas can easily take you from the office to date night while looking and feeling great. Be sure to explore our new arrivals to make sure you don't miss any of the latest styles in stock.