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Men's City's Edge Waterproof Chukka Boots

Men's City's Edge Waterproof Chukka Boots

Just try on a pair. If the gorgeous leathers and clean lines of our City's Edge waterproof chukkas don't convince you that your feet must have these, let the cushiony footbeds speak for themselves.

Men's Davis Square Mixed-Media Chukka Shoes

Men's Davis Square Mixed-Media Chukka Shoes

Today's going to be an adventure. Make sure you're wearing a new pair that can handle it! Our Davis Square mixed-media chukkas feature recycled materials, cushiony footbeds and streamlined styling that's great dressed up or down.

Men's Desus & Mero x Timberland® Waterproof 6-inch

Men's Desus & Mero x Timberland® Waterproof 6-inch

Desus & Mero (aka the Bodega Boys) have put their spin on Timberland's waterproof leather 6-inch boots. The linings and insulation are made using recycled plastic.

Men's Groveton Plain-Toe Chukka Shoes

Men's Groveton Plain-Toe Chukka Shoes

When you're laced up into the right pair of shoes, you're ready to seize the day. Wherever you're headed, the lug outsoles and cushiony footbeds in our Groveton leather chukkas will get there faster, unless you feel like taking your ...