Men's Chelsea Boots

170 Results
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170 Results
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Clearance
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Crown Vintage Lanbart Chelsea Boot

Minimum Clearance Price $64.98 $64.98
★★★★★ ★★★★★
(19)
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Florsheim Anthem Chelsea Boot

$144.99
Extra 20% off reg. price!
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Deer Stags Rockland Boot

Now $59.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(22)
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Dr. Martens Embury Chelsea Boot

$139.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(8)
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Rockport Cassius Chelsea Boot

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

Now $69.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(22)
New Arrival
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Steve Madden Brompton Chelsea Boot

$139.99
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Carhartt Frontier Soft Toe Work Chelsea Boot - Men's

$139.99
★★★★★ ★★★★★
(37)
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Bogs Digger Waterproof Rain Boot

$84.99
★★★★★ ★★★★★
(1)
Top Rated
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Florsheim Rucci Chelsea Boot

Now $119.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(6)
New Arrival
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Merrell Moab Adventure 3 Waterproof Chelsea Boot

$169.99
★★★★★ ★★★★★
(42)
Clearance
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Top Rated
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Dr. Martens Hardie II Chelsea Boot - Men's

$129.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(23)
Clearance
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Steve Madden Rialto Chelsea Boot

Minimum Clearance Price $84.98 $84.98
★★★★★ ★★★★★
(4)
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Wolverine I-90 EPX Romeo CarbonMAX Toe Work Boot - Men's

Now $169.99
★★★★★ ★★★★★
(5)
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Dockers Truman Chelsea Boot

Now $69.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(8)
New Arrival
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Clarks Jaxen Easy Chelsea Boot

Now $99.99
Extra 20% off reg. price!
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Florsheim Forge Plain Toe Chelsea Boot

$129.99
★★★★★ ★★★★★
(1)
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Nunn Bush Otis II Chelsea Boot

Now $99.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(2)
Top Rated
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Carlos by Carlos Santana Mantra Boot

$158.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(38)
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HUNTER Original Chelsea Rain Boot - Men's

$174.96
New Arrival
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Carhartt Chelsea Work Boot - Men's

$154.99
★★★★★ ★★★★★
(15)
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Bogs Sauvie Chelsea II Boot - Men's

$109.99
★★★★★ ★★★★★
(2)
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Bogs Rockaway Rain Boot - Men's

$129.99
Top Rated
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Carhartt Frontier Steel Toe Work Chelsea Boot - Men's

$149.99
★★★★★ ★★★★★
(12)
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HUNTER Landon Chelsea Boot - Men's

$189.96
Top Rated
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Kenneth Cole New York Tully Chelsea Boot

$184.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(4)
Clearance
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Florsheim Rucci Chelsea Boot

Minimum Clearance Price $103.98 $103.98
★★★★★ ★★★★★
(10)
Top Rated
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Georgia Boot Romeo Superlyte Work Slip-On - Men's

$104.99
★★★★★ ★★★★★
(4)
Top Rated
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Florsheim Loedin Steel Toe Work Boot

Now $144.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(10)
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Carhartt Force Romeo Soft Toe Boot - Men's

$149.99
★★★★★ ★★★★★
(4)
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Totes Isotoner Chelsea Rain Boot - Men's

$59.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(111)
Clearance
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Frye & Co. Hank Chelsea Boot

Minimum Clearance Price $114.98 $114.98
★★★★★ ★★★★★
(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.