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Men's Chelsea Boots

142 Results
Top Rated
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Mix No. 6 Aleder Chelsea Boot

Now $59.99 Maximum Clearance Price $69.99 $69.99
★★★★★ ★★★★★
(43)
Clearance
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Rockport Cassius Chelsea Boot

Now $119.99
★★★★★ ★★★★★
(2)
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Florsheim Anthem Chelsea Boot

$144.99
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Caterpillar Wheelbase Steel Toe Work Boot - Men's

$109.99
★★★★★ ★★★★★
(1)
Clearance
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New Arrival
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Florsheim Rucci Chelsea Boot

Now $139.99
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Florsheim Forge Plain Toe Chelsea Boot

$129.99
★★★★★ ★★★★★
(1)
Top Rated
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Carlos by Carlos Santana Mantra Boot

$158.99
★★★★★ ★★★★★
(38)
Top Rated
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Carhartt Frontier Steel Toe Work Chelsea Boot - Men's

$149.99
★★★★★ ★★★★★
(12)
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Bogs Digger Waterproof Rain Boot

$84.99
★★★★★ ★★★★★
(1)
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HUNTER Landon Chelsea Boot - Men's

$189.96
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Vance Salter Chelsea Boot

Now $79.99
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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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Carhartt Frontier Soft Toe Work Chelsea Boot - Men's

$139.99
★★★★★ ★★★★★
(37)
Top Rated
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Carhartt Millbrook Romeo Steel Toe Wedge Work Boot - Men's

$149.99
★★★★★ ★★★★★
(13)
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Georgia Boot Romeo Steel Toe Work Boot

$114.99
★★★★★ ★★★★★
(67)
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Iron Age Groundbreaker Slip On Steel Toe Work Boot

Now $144.99
★★★★★ ★★★★★
(40)
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Nunn Bush Otis II Chelsea Boot

Now $99.99
★★★★★ ★★★★★
(2)
Top Rated
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Florsheim Loedin Steel Toe Work Boot

Now $144.99
★★★★★ ★★★★★
(10)
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Caterpillar Striver Steel Toe Chelsea Work Boot - Men's

Now $109.99
★★★★★ ★★★★★
(1)
Clearance
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Nunn Bush Karnak Chelsea Boot

Now $89.99
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A. Veer Lenox Chelsea Boot

$178.99
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Dune London Matchin Chelsea Boot

$179.99
New Arrival
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Nunn Bush Briggs Chelsea Boot

Now $99.99
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A. Veer Stratus Chelsea Boot

$178.99
New Arrival
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Carlos by Carlos Santana Mantra Chelsea Boot

$158.99
New Arrival
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New Arrival
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Clearance
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Dockers Truman Chelsea Boot

Now $69.99
★★★★★ ★★★★★
(7)
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Steve Madden Brompton Chelsea Boot

$139.99
Top Rated
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Timberland Men's Britton Road Chelsea Boot

$159.99
★★★★★ ★★★★★
(41)
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Vance Landon Boot

Now $69.99
★★★★★ ★★★★★
(313)
New Arrival
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New Arrival
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Totes Isotoner Chelsea Rain Boot - Men's

$59.99
★★★★★ ★★★★★
(111)
Top Rated
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Florsheim Rucci Chelsea Boot

Now $119.99
★★★★★ ★★★★★
(6)
Clearance
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Steve Madden Highline Boot - Men's

Minimum Clearance Price $79.98 $79.98
Up to 60% off clearance!
★★★★★ ★★★★★
(25)
Top Rated
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Kenneth Cole New York Tully Chelsea Boot

$184.99
★★★★★ ★★★★★
(4)
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Georgia Boot Romeo Superlyte Work Slip-On - Men's

$104.99
★★★★★ ★★★★★
(6)
New Arrival
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Top Rated
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Anthony Veer Jefferson Chelsea Boot

Now $139.99
★★★★★ ★★★★★
(3)
Top Rated
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Carlos by Carlos Santana Mantra Boot

Now $95.99
★★★★★ ★★★★★
(6)
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Dockers Dylan Chelsea Boot

Now $69.99
★★★★★ ★★★★★
(5)
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Georgia Boot High Romero Steel Toe Work Boot

$144.99
★★★★★ ★★★★★
(59)

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.