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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 Redwood Falls Waterproof Chukka Boots

Featuring an extra-cushiony interior, an easy-to-wear ankle height, and a pull-tab for easy on/off, our Redwood Falls men's chukkas also offer the superior traction of our patented L7 multi-directional lug design. Plus, they're responsibly crafted with eco-conscious materials. TIMBERLAND | ...

Men's Heritage 6-Inch Waterproof Boots

Inspired by our original yellow boot, this men's waterproof style puts an emphasis on comfort, with padded collars, an anti-fatigue footbed, arch support, amd 400 grams of warm PrimaLoft® insulation. They also tread lightly on the planet with leather from ...

Men's Premium 6-Inch Waterproof Boots

Our original waterproof boot. This all-season style offers tireless performance and instantly recognizable styling. Other essential features include 400 grams of warm, down-free PrimaLoft® insulation, a padded collar for a comfortable fit around the ankle, a rubber lug outsole for ...