Men's Chelsea Boots

155 Results
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155 Results
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Florsheim Anthem Chelsea Boot

$144.99
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Tommy Hilfiger Solter Boot

Now $89.99
Clearance
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Rockport Cassius Chelsea Boot

Now $119.99
★★★★★ ★★★★★
(2)
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Dockers Dylan Chelsea Boot

Now $69.99
★★★★★ ★★★★★
(5)
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Nunn Bush Briggs Chelsea Boot

Now $99.99
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Nunn Bush Otis II Chelsea Boot

Now $99.99
★★★★★ ★★★★★
(2)
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Stacy Adams Berkshire Boot

Now $119.99
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Florsheim Rucci Chelsea Boot

Now $139.99
Clearance
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Deer Stags Rockland Boot

Now $64.99
★★★★★ ★★★★★
(22)
New Arrival
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Calvin Klein Volminer Chelsea Boot

Now $149.99
Top Rated
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Florsheim Rucci Chelsea Boot

Now $119.99
★★★★★ ★★★★★
(6)
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Carhartt Frontier Soft Toe Work Chelsea Boot - Men's

$139.99
★★★★★ ★★★★★
(37)
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Dockers Truman Chelsea Boot

Now $69.99
★★★★★ ★★★★★
(8)
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Vance Salter Chelsea Boot

Now $79.99
Top Rated
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Carhartt Frontier Steel Toe Work Chelsea Boot - Men's

$149.99
★★★★★ ★★★★★
(12)
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Dune London Matchin Chelsea Boot

$179.99
Top Rated
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Carlos by Carlos Santana Mantra Boot

$158.99
★★★★★ ★★★★★
(38)
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Nunn Bush Delton Chelsea Boot

Now $69.99
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HUNTER Orford Rain Boot - Men's

$194.96
Top Rated
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Dr. Martens Hardie II Chelsea Boot - Men's

$129.99
★★★★★ ★★★★★
(23)
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Timberland Men's Britton Road Chelsea Boot

$169.99
★★★★★ ★★★★★
(2)
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Carhartt Millbrook Romeo Steel Toe Work Boot - Men's

$154.99
★★★★★ ★★★★★
(2)
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Caterpillar Striver Steel Toe Chelsea Work Boot - Men's

Now $109.99
★★★★★ ★★★★★
(1)
Clearance
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Bogs Rockaway Rain Boot - Men's

$129.99
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Carhartt Chelsea Work Boot - Men's

$154.99
★★★★★ ★★★★★
(15)
Clearance
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Top Rated
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Florsheim Loedin Steel Toe Work Boot

Now $144.99
★★★★★ ★★★★★
(10)
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Totes Isotoner Chelsea Rain Boot - Men's

$59.99
★★★★★ ★★★★★
(111)
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HUNTER Original Chelsea Rain Boot - Men's

$174.96
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
★★★★★ ★★★★★
(1)
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Vance Josiah Chelsea Boot

Now $89.99
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Bogs Digger Waterproof Rain Boot

$84.99
★★★★★ ★★★★★
(1)
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A. Veer Beckett Chelsea Boot

$178.99
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Anthony Veer Ashford Chelsea Boot

$328.99
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ALDO Collen Boot

$119.99
★★★★★ ★★★★★
(1)
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A. Veer Dwayne Chelsea Boot

Now $110.99 Maximum Clearance Price $158.99 $158.99
★★★★★ ★★★★★
(1)
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Caterpillar Wheelbase Steel Toe Work Boot - Men's

$109.99
★★★★★ ★★★★★
(1)
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Georgia Boot Romeo Superlyte Work Slip-On - Men's

$104.99
★★★★★ ★★★★★
(6)
Clearance
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New Arrival
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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.