Men's Chelsea Boots

152 Results
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152 Results
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Florsheim Anthem Chelsea Boot

$144.99
Extra 20% off for VIPs!
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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!
Clearance
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Dockers Dylan Chelsea Boot

Now $69.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(5)
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Deer Stags Rockland Boot

Now $64.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(22)
Top Rated
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Florsheim Rucci Chelsea Boot

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

Now $69.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(8)
Top Rated
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Carlos by Carlos Santana Mantra Boot

$158.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(38)
Clearance
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Caterpillar Wheelbase Steel Toe Work Boot - Men's

$109.99
★★★★★ ★★★★★
(1)
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HUNTER Orford Rain Boot - Men's

$194.96
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Carhartt Frontier Soft Toe Work Chelsea Boot - Men's

$139.99
★★★★★ ★★★★★
(37)
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Nunn Bush Otis II Chelsea Boot

Now $99.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(2)
Top Rated
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Florsheim Loedin Steel Toe Work Boot

Now $144.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(10)
Clearance
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Steve Madden Brompton Chelsea Boot

$139.99
Top Rated
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Carhartt Frontier Steel Toe Work Chelsea Boot - Men's

$149.99
★★★★★ ★★★★★
(12)
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Carhartt Millbrook Romeo Steel Toe Work Boot - Men's

$154.99
★★★★★ ★★★★★
(2)
Top Rated
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Carhartt Chelsea Steel Toe Work Boot - Men's

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★★★★★ ★★★★★
(14)
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Florsheim Forge Plain Toe Chelsea Boot

$129.99
★★★★★ ★★★★★
(1)
Top Rated
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Dr. Martens Hardie II Chelsea Boot - Men's

$129.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(23)
Clearance
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Clearance
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Clearance
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Frye & Co. Hank Chelsea Boot

Minimum Clearance Price $114.98 $114.98
★★★★★ ★★★★★
(3)
New Arrival
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Spring Step Blevins Chelsea Boot

$189.99
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Bogs Rockaway Rain Boot - Men's

$129.99
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Totes Isotoner Chelsea Rain Boot - Men's

$59.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(111)
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A. Veer Dwayne Chelsea Boot

Now $99.99 Maximum Clearance Price $158.99 $158.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(1)
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Blundstone Original 510 Chelsea Boot

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★★★★★ ★★★★★
(1)
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ALDO Collen Boot

$119.99
★★★★★ ★★★★★
(1)
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Timberland Men's Britton Road Chelsea Boot

$169.99
★★★★★ ★★★★★
(2)
Top Rated
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Vance Marshall Boot

Now $69.99
Extra 20% off for VIPs!
★★★★★ ★★★★★
(57)

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.