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The Best Men's Chelsea Boots (2020 Update)

One of the most iconic and versatile boots that money can buy, Chelsea boots are unique because they’re durable enough for winter but often lightweight enough for year-round wear. Here are our top recommendations for guys who understand quality and don’t want to pay a high retail mark-up for a great looking pair of boots that are built to last.

The Best Men's Chelsea Boots (2020 Update)

The Best Modern Chelsea Boot: The Shadow Grey Suede Cavalier

Key features: Shadow Grey WeatherSafe™ Suede, Poron® Shock-Absorbing Insole, Flexible Elastic Goring.

Why we love it: A sleek take on classic silhouette, this dress Chelsea boot looks right at home with a suit or your favorite pair of jeans. It’s stylish, but never stuffy, and it’s built with the materials to stay in form for years to come. Easy to dress up or down, this boot is as versatile as the man who wears it.

What people are saying: “Their take on the Chelsea boot is perfectly understated and well made.” - Men’s Journal

The Best Modern Chelsea Boot: <a href="">The Shadow Grey Suede Cavalier</a>

The Best Casual Chelsea Boot: The Honey Suede Duke

Key features: Honey WeatherSafe™ Suede, Poron® Antimicrobial Shock Absorbing Insole, DuraEVA™ Comfort Strip, Durable Studded Rubber Outsoles.

Why we love it: This classic Chelsea boot elevates your daily wardrobe to keep you looking cool and relaxed, no matter what you pair with it. While Honey Suede has long been one of our favorite colors because of how versatile it is, the Duke comes in several different colors and leathers to ensure you find the right pair for your daily grind.

What people are saying: “Thursday Boot Company has found a perfect balance of high quality materials and reasonable cost.” - Mark W.

Also available in: Black, Brown, Dark Olive Suede, Chocolate.

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The Best Casual Chelsea Boot: <a href="">The Honey Suede Duke</a>

The Best Rugged Chelsea Boot: The Black Matte Legend

Key features: Black Matte Rugged & Resilient Leather, Poron® Antimicrobial Shock Absorbing Insole, Hardwearing Steel Shank, StormKing™ Durable Rubber Lug Outsole.

Why we love it: The Legend blends form and function like nothing you’ve seen anywhere else. This hardwearing Chelsea boot is every bit as comfortable as you’d expect from a slip-on boot but with the durability of our Rugged & Resilient collection. Handcrafted for the men who wear their boots hard, every detail was carefully selected so you can go the extra mile with confidence.

What people are saying: “Great boot, perfect look and great quality. I even caught someone trying to sneak a picture of the boots. I even moved them to the side for a better angle for them.” - Gilbert G.

Also available in Safari and Bourbon.

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