Black Friday Preview Event

Extra 30% Off

Sale on Sale
SPERRY is offering an extra 30% off sale styles. 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 November 4th at 10:00am to November 18th, 2025 at 11:59pm EST. Subject to change at any time.
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Chelsea Boots for Men

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’Tis the Sea-son
The Sperry Holiday Gift Guide

Timeless style, made to give. From cozy slippers to weather-ready boots and everyday icons, discover gifts they’ll reach for all season long. Thoughtful, crafted, and built to last.

Women's Gift Guide
Men's Gift Guide
Browse our Gift Gude

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.