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Up to 40% off fall favorites, select styles only. Prices as marked. Offer ends October 4, 2020 at 11:59PM ET. Offer does not apply on previous purchases, and cannot be combined with other offers. Offer valid only on Sperry.com. Valid on US orders only. Some restrictions may apply.
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.
As the weather cools down, your comfort shouldn't be compromised. Stay warm and cozy in men's fall boots from Sperry. Our classic leather boots for men include stylish men's chukkas, designed with genuine hand-sewn leather uppers for style, luxury lambskin linings for warmth and molded Ortholite® heel cups for enhanced shock absorption. With all-day comfort and style, you'll be ready for any rugged or urban adventure that comes your way. Featuring non-marking molded outsoles for outstanding cushioning and traction in both wet and dry conditions, our men's fall boots will have you set you explore from the shore to the stores this holiday season. If you prefer a more lightweight fall shoe, opt for a version of our Striper Alpine cool weather boots. These waxed canvas chukkas are lighter than our classic leather boots for men, but just as durable and comfortable. When you're ready to tackle the cooler season's most exhilarating adventures, grab a pair of men's fall boots from Sperry for fearless confidence in every step.