Men's Chelsea Boots

172 Results
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172 Results
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Dr. Martens Embury Chelsea Boot

$139.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(8)
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Florsheim Anthem Chelsea Boot

$144.99
Extra 20% off for VIPs!
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Deer Stags Rockland Boot

Now $59.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(22)
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Stacy Adams Berkshire Boot

Now $119.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(1)
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Clarks Jaxen Easy Chelsea Boot

Now $74.99
Limited time! Up to 40% off
Top Rated
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Dockers Dylan Chelsea Boot

Now $69.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(33)
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Carhartt Frontier Soft Toe Work Chelsea Boot - Men's

$139.99
★★★★★ ★★★★★
(37)
Top Rated
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Florsheim Rucci Chelsea Boot

Now $119.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(6)
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Rockport Cassius Chelsea Boot

Now $119.99
★★★★★ ★★★★★
(2)
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Tommy Hilfiger Solter Boot

Now $89.99
Extra 20% off for VIPs!
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Dockers Truman Chelsea Boot

Now $69.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(8)
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Steve Madden Brompton Chelsea Boot

$139.99
New Arrival
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Merrell Moab Adventure 3 Waterproof Chelsea Boot

$169.99
★★★★★ ★★★★★
(44)
Top Rated
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Nunn Bush Otis II Chelsea Boot

Now $99.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(3)
Top Rated
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Carlos by Carlos Santana Mantra Boot

$158.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(38)
Top Rated
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Dr. Martens Hardie II Chelsea Boot - Men's

$129.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(23)
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Georgia Boot Romeo Superlyte Work Slip-On - Men's

$104.99
★★★★★ ★★★★★
(6)
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Bogs Rockaway Rain Boot - Men's

$124.99
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Carhartt Force Romeo Soft Toe Boot - Men's

Now $99.99
★★★★★ ★★★★★
(4)
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(1)
Top Rated
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Florsheim Loedin Steel Toe Work Boot

Now $144.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(10)
Top Rated
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Carhartt Millbrook Romeo Steel Toe Wedge Work Boot - Men's

$149.99
★★★★★ ★★★★★
(13)
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Florsheim Forge Plain Toe Chelsea Boot

$129.99
★★★★★ ★★★★★
(1)
Top Rated
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Georgia Boot Romeo Superlyte Work Slip-On - Men's

$104.99
★★★★★ ★★★★★
(4)
Top Rated
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Kenneth Cole New York Tully Chelsea Boot

$184.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(4)
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Bogs Digger Waterproof Rain Boot

$84.99
★★★★★ ★★★★★
(1)
Top Rated
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Carhartt Chelsea Steel Toe Work Boot - Men's

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★★★★★ ★★★★★
(14)
Clearance
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Top Rated
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Florsheim Hercules Steel Toe Work Boot

Now $174.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(3)

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.