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Men's Adventure Cupsole Chukka Shoes

Men's Adventure Cupsole Chukka Shoes

Not your average men's shoes. Crafted from a premium mix of leathers and suedes, these chukkas mix athletic and refined styling with their comfy padded collars, traction-loving siped outsoles and streamlined style.

Men’s Timberland® American Craft Waterproof Chukka Boots

Men’s Timberland® American Craft Waterproof Chukka Boots

Made with premium waterproof Horween® leathers, the American Craft collection is designed and handmade in the United States by dedicated craftspeople who understand that time, skill and the best-quality materials are what makes a truly exceptional boot.

Men's Davis Square Waterproof Chukkas

Men's Davis Square Waterproof Chukkas

Stay warm this winter with waterproof chukkas lined with faux fur and featuring eco-conscious LITE Leather and ReBOTL™ fabric containing at least 50% recycled plastic.

Men's Earthkeepers® Original Leather Chukka Boots

Men's Earthkeepers® Original Leather Chukka Boots

These durable men's chukkas feature a comfy anti-fatigue footbed and are eco-consciously made with responsibly sourced leathers and ReBOTL™ fabric containing at least 50% recycled plastic.