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As comfy as a slipper, yet ready for the great outdoors. Our Ashwood Park men's chukkas cradle your foot with a lightweight OrthoLite® footbed and warm Teddy fleece lining at the collar and tongue. A rugged outsole helps prevent slips. ...

Men's Boulder Trail Waterproof Chukka Boots

Combining the durability of a boot with the comfort of a sneaker, this men's waterproof style features a rubber lug outsole for traction and materials sourced to respect the planet as much as you do. TIMBERLAND | Men's Boulder Trail Waterproof ...

Men's Davis Square Boots

These men's mixed-media boots were designed for comfort, with a lightweight OrthoLite® footbed, padded collar, and rubber outsole. Plus, they're made with eco-conscious materials. TIMBERLAND | Men's Davis Square Boots.

Men's Earthkeepers® Original 6-Inch Leather Boots

Originally released in 2007, this boot was the start of the Earthkeepers® Edition that's grown to include shoes, clothes, and more. These boots are made for comfort and versatility with EVA-blend foam cushioning, rugged rubber outsoles, and arch support. And ...