Back To Top Chukkas - Showing 20 Items Sort: Recommended Prices: Low to High Prices: High to Low Rating FILTERS Style Chukka (19) Dress Boots (4) Hiking Boots (1) Features Ortholite® Insoles (12) Waterproof (10) Anti-Fatigue Technology (4) Gore-Tex® Membrane (1) Water-Resistant (1) Shoe Size 8 10.5 7 7.5 8.5 9 10 11 11.5 13 9.5 12 14 15 Width Medium (19) Wide (4) Color Wheat/Yellow Black Brown/Tan Grey Orange PRICE < $100.00 (2) $100.00 - $200.00 (18) DONE RESET Men's Redwood Falls Waterproof Chukkas $130.00 Men's Davis Square Leather Collar Chukka Shoes $90.00 Men's Davis Square Mixed-Media Chukka Shoes $85.00 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 Timberland Boot Company® Wodehouse Chukka Boots $300.00 $119.99 60% off 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 GORE-TEX® Men's Timberland® Waterproof Chukka Boots $155.00 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.