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Men's Chelsea Boots

131 Results
Top Rated
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Mix No. 6 Aleder Chelsea Boot

Now $59.99 Maximum Clearance Price $69.99 $69.99
BOGO 50% off!
★★★★★ ★★★★★
(43)
Clearance
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Top Rated
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Florsheim Rucci Chelsea Boot

Now $129.99
BOGO 50% off!
★★★★★ ★★★★★
(10)
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Florsheim Anthem Chelsea Boot

$144.99
BOGO 50% off!
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Caterpillar Wheelbase Steel Toe Work Boot - Men's

$109.99
BOGO 1st pair only!
★★★★★ ★★★★★
(1)
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Bogs Digger Waterproof Rain Boot

$84.99
BOGO 1st pair only!
★★★★★ ★★★★★
(1)
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Rockport Cassius Chelsea Boot

Now $119.99
BOGO 1st pair only!
★★★★★ ★★★★★
(2)
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Dockers Truman Chelsea Boot

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(7)
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Dr. Martens Embury Chelsea Boot

$139.99
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★★★★★ ★★★★★
(8)
Top Rated
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Florsheim Rucci Chelsea Boot

Now $119.99
BOGO 50% off!
★★★★★ ★★★★★
(6)
Top Rated
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Bogs Rockaway Rain Boot - Men's

$119.99
BOGO 1st pair only!
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Bogs Rockaway Rain Boot - Men's

$124.99
BOGO 1st pair only!
Top Rated
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Carlos by Carlos Santana Mantra Boot

$158.99
BOGO 50% off!
★★★★★ ★★★★★
(38)
Top Rated
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Totes Isotoner Chelsea Rain Boot - Men's

$59.99
BOGO 50% off!
★★★★★ ★★★★★
(111)
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Florsheim Forge Plain Toe Chelsea Boot

$129.99
BOGO 1st pair only!
★★★★★ ★★★★★
(1)
Clearance
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Clearance
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Carhartt Frontier Soft Toe Work Chelsea Boot - Men's

$139.99
BOGO 1st pair only!
★★★★★ ★★★★★
(35)
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Nunn Bush Otis II Chelsea Boot

Now $99.99
BOGO 50% off!
★★★★★ ★★★★★
(2)
New Arrival
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Timberland Men's Britton Road Chelsea Boot

$159.99
BOGO 50% off!
★★★★★ ★★★★★
(41)
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Vance Landon Boot

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(313)
Clearance
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Top Rated
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Florsheim Loedin Steel Toe Work Boot

Now $144.99
BOGO 50% off!
★★★★★ ★★★★★
(10)
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Dockers Dylan Chelsea Boot

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(5)
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Steve Madden Brompton Chelsea Boot

$139.99
BOGO 1st pair only!
Top Rated
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Vance Marshall Boot

Now $49.99 Maximum Clearance Price $69.99 $69.99
BOGO 50% off!
★★★★★ ★★★★★
(57)
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A. Veer Stratus Chelsea Boot

$178.99
BOGO 50% off!
Top Rated
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Stacy Adams Maury Chelsea Boot

Now $109.99
BOGO 50% off!
★★★★★ ★★★★★
(7)
Top Rated
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Vance Garrett Cap Toe Boot

Now $44.99
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★★★★★ ★★★★★
(15)
Clearance
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Vance Marshon Chelsea Boot

Now $39.99
BOGO 50% off!
★★★★★ ★★★★★
(8)
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Bogs Sauvie Chelsea II Boot - Men's

$109.99
BOGO 1st pair only!
★★★★★ ★★★★★
(2)
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Blundstone Original 500 Chelsea Boot

$199.99
BOGO 1st pair only!
★★★★★ ★★★★★
(1)
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Stacy Adams Bradley Chelsea Boot

$154.99
BOGO 50% off!
★★★★★ ★★★★★
(2)
Clearance
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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.