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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.