Back To Top Chukkas - Showing 29 Items Sort: Recommended Prices: Low to High Prices: High to Low Rating FILTERS Product Type Footwear (28) Style Chukka (26) Dress Boots (3) Ankle Boots (2) Hiking Boots (1) Winter (1) Features Recycled Content (14) Ortholite® Insoles (13) Waterproof (13) Anti-Fatigue Technology (5) Gore-Tex® Membrane (1) Water-Resistant (1) Shoe Size 7 8 10 10.5 11 8.5 9 9.5 7.5 11.5 12 13 14 15 Width Medium (27) Wide (9) Color Brown/Tan Black Wheat/Yellow Grey Orange Gender Men (28) PRICE < $100.00 (3) $100.00 - $200.00 (26) DONE RESET Men's Redwood Falls Waterproof Chukkas $130.00 Men's Oakrock Waterproof Chukka Boots $150.00 Men's Stormbuck Waterproof Chukka Shoes $150.00 Men's Davis Square Mixed-Media Chukka Shoes $85.00 Men's Davis Square Leather Collar Chukka Shoes $90.00 Men's Timberland Originals Chukka Boots $150.00 Men's Port Union Waterproof Chukka Boots $165.00 Men's Kendrick Waterproof Chukka Boots $160.00 Men's Squall Canyon Waterproof Chukka Boots $150.00 Men's Yorkdale Chukka Boots $110.00 Men's Classic Waterproof Chukka Boots $135.00 Men's Classic Waterproof Chukka Boots $135.00 Men's Timberland® Icon Waterproof Chukka Boots $160.00 Men's Davis Square Waterproof Chukkas $120.00 Men's Davis Square Waterproof Chukkas $120.00 Men's Cross Mark Waterproof Chukkas with GORE-TEX Fabric $160.00 Men's Tenmile Chukka Boots $110.00 Men's Mt. Maddsen Waterproof Chukka Boots $120.00 Tenmile Chukka Boots $110.00 Men's CityRoam™ Cupsole Chukka Shoes $140.00 Men's Killington Leather Chukka Sneaker Boots $125.00 Men's Bradstreet Leather Chukka Sneaker Boots $120.00 GORE-TEX® Men's Cross Mark Waterproof Chukka Shoes $160.00 Men's Bradstreet Leather Chukka Sneaker Boots $120.00 ???PROMOTION_PICK_FREE_GIFTS??? [ES_PRODUCT_GRID_SPLIT_RECOMMENDATION_1] We have men's chukka boots for every occasion. Our men's boots are crafted with high quality materials using modern technology for durability and comfort. Finish the look with a pair of our pants or chinos for a tailored but casual look.