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Men's Chelsea Boots

151 Results
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Rockport Cassius Chelsea Boot

Now $119.99
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Florsheim Anthem Chelsea Boot

$144.99
Top Rated
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Carlos by Carlos Santana Mantra Boot

Now $148.99
★★★★★ ★★★★★
(38)
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Vance Landon Boot

Now $49.99
★★★★★ ★★★★★
(312)
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Nunn Bush Delton Chelsea Boot

Now $69.99
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Vance Salter Chelsea Boot

Now $79.99
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Dune London Matchin Chelsea Boot

$179.99
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Vance Josiah Chelsea Boot

Now $89.99
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Nunn Bush Karnak Chelsea Boot

Now $89.99
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Steve Madden Brompton Chelsea Boot

$139.99
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HUNTER Original Chelsea Rain Boot - Men's

$174.96
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Vance Osmond Chelsea Boot

Now $89.99
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A. Veer Stratus Chelsea Boot

$178.99
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Steve Madden Montreux Chelsea Boot

$139.99

Who knew having the best boots in the room was such a flex? Well, we did. For effortlessly fresh ‘fits, upgrade your boot game with the classic Men’s Chelsea boot. Never out of style, always looks good, and goes with everything, you might consider this the greatest boot of all time. 

Season to season, this timeless essential makes the whole “dress it up or down” thing look easy. Hanging out with the guys? Step into comfortable (emphasis on comfortable) Chelsea boots with a suede or canvas finish from must-own brands Cole Haan and Crown Vintage. With jeans or khakis, these materials are ideal for a casual dress code. Plus, the rounded toe means plenty of room for your feet to breath. Date night, night out, or just feeling fancy, try a men’s leather Chelsea boot from brands Vince Camuto, Stacy Adams, and Dr. Martens. 

Pair with some slacks or trousers, the leather finish is the easiest way to take your style from casual to something more dressy. Stock up on the latest men's boots and other dress boots waiting for you at your favorite DSW store, online at dsw.com, or in the DSW app.