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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 Davis Square Chukka Boots

A cushioned footbed and padded collar are among the comfort features built into these men's mixed-media chukkas. They also feature Defender Repellent Systems® treatment to help repel stains and eco-consciously sourced materials. TIMBERLAND | Men's Davis Square Chukka Boots.

Men's Timbercycle EK+ Chukka Boots

These go-anywhere men's chukkas are a wardrobe essential. They're also responsibly made with recycled leather uppers and Responsible Natural Rubber outsoles that seek to guard against rainforest deforestation by sourcing from responsibly managed rubber plantations. TIMBERLAND | Men's Timbercycle EK+ ...

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 ...