Cold Weather, Hot Prices

Extra 20% Off Boots

Limited Time Only
SPERRY is offering 20% off select boots. Discount automatically applied at checkout. Discount applicable before taxes and shipping costs. Some exclusions may apply. Not applicable to prior purchases. Cannot be combined with any other offer. Valid online from December 9th at 5:00pm to December22nd, 2025 at 11:59 pm EST. Subject to change at any time.
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Chelsea Boots for Men

A boater for all seasons
Best of boat

Whether shearling-lined or dressed up in dark hues, consider it your year-round staple. From the classic Authentic Original™ Boat Shoe to the Billfish, discover the MVP styles that set the standard.

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Discover the refined craftsmanship of Sperry’s Chelsea boots for men, where timeless design meets modern versatility. Built from premium leather and designed for everyday wear, our men’s Chelsea boots deliver comfort, durability, and effortless style in any season. Whether you’re dressing up for the office or keeping it casual on the weekend, these boots offer the perfect balance of rugged appeal and polished sophistication. With options including waterproof Chelsea boots and weather-ready soles, Sperry ensures you’re ready for any adventure. Step confidently into classic coastal heritage with our Chelsea boots for men, made to last and crafted to impress.