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Save up to 60% off select styles. Offer valid through January 31st, 2022 at 11:59 PM PT. Offer valid on styles within Sperry.com/sale only. While supplies last. Offer does not apply on previous purchases, and cannot be combined with other offers. Offer applies to US orders only. Some restrictions may apply.
Free express shipping on full price Gold Cup styles. Offer automatically applied at checkout.
Get 20% off your next purchase when you refer a friend to Sperry.com. Your friend will receive 20% off their purchase of $75+ at Sperry.com. Please read all terms and conditions. Offer valid on US orders only. Some restrictions may apply.
87 Products
87 Products
Be ready for any adventure – from the office park to the actual park – in men's chukka boots from Sperry. Our wide selection of men's casual boots is designed to keep you steady, comfortable and stylish wherever your journey takes you. From strolling on the beach, boardwalk or promenade to hailing a cab for your next big night out, your new men's chukka boots will stand up to the weather and stand out in the crowd. Our carefully crafted designs feature waterproof, seam-sealed construction, non-marking rubber outsoles, heavy lugs and Wave-Siping™ for the ultimate in wet/dry protection and traction, plus rawhide laces, premium leather accents and genuine, hand-sewn details for unbeatable charm. Classic Sperry styling ensures our men's chukka boots will help you handle any endeavor with confidence. From simple, slip-on and sneaker styles to high-top duck boots made to protect your every step, you're sure to find a Sperry chukka style you love. Whatever your next quest demands of you, keep comfortable men's casual boots from Sperry.
