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Men's Leather Ankle Boots
Men's Leather Ankle Boots
Sale price$141.99 USD
No reviews
Men's Leather Ankle Boots
Men's Leather Ankle Boots
Sale price$149.99 USD
No reviews
Men's Leather Ankle Boots OS-5008-8-E-F
Men's Leather Ankle Boots OS-5008-8-E-F
Sale price$169.99 USD
No reviews
Men's Leather Ankle Boots OS-6015-7-Vintage-US-R
Men's Leather Ankle Boots OSS-5008-8-H-Vintage DarkBrown
Men's Leather Ankle Boots OSS-6015-1-C-E
Men's Leather Ankle Boots OSS-6015-1-C-E
Sale price$139.99 USD
1 review
Men's Leather Ankle Boots OSS-6015-2-Retro Brown
Men's Leather Ankle Boots OSS-6015-2-Retro Brown
Sale price$149.99 USD
93 reviews
Men's Leather Ankle Boots OSS-6015-3-A
Men's Leather Ankle Boots OSS-6015-3-A
Sale price$129.99 USD
No reviews
Men's Leather Ankle Boots OSS-6015-3-B-D
Men's Leather Ankle Boots OSS-6015-3-B-D
Sale price$149.99 USD
No reviews
Men's Leather Ankle Boots OSS-6015-3-E
Men's Leather Ankle Boots OSS-6015-3-E
Sale price$149.99 USD
No reviews
Men's Leather Ankle Boots OSS-6015-3-F Distressed Brown
Men's Leather Ankle Boots OSS-6015-6-Retro Brown
Men's Leather Ankle Boots OSS-6015-6-Retro Brown
Sale priceFrom $139.99 USD
No reviews

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Timeless. Versatile. Effortless.

Osstone Chukka Boots bring together timeless design and modern comfort. Each pair is handcrafted with retro craftsmanship and a hand-stitched welt, using premium cowhide leather that feels broken-in from day one. Finished with lightweight, durable rubber soles, they’re perfect for everything from casual weekends in jeans to smart-casual looks with chinos or a blazer. Stylish, versatile, and built to last—Chukkas that truly fit your lifestyle.