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Men's Chukka Boots

111 Results

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111 Results
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Crown Vintage Patton Chukka Boot

Now $79.99
$15, $20, or $60 off!
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Clarks Shepton Chukka Boot

$59.99 – Maximum Clearance Price $74.98 $74.98
Limited time! Up to 40% off
★★★★★ ★★★★★
(5)
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Rockport Merrick Waterproof Boot

Now $119.99
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Timberland Auburn Falls Waterproof Chukka Boot - Men's

$139.99
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Timberland Auburn Falls Waterproof Chukka Boot - Men's

$139.99
★★★★★ ★★★★★
(2)
Top Rated
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Nunn Bush Circuit Plain Toe Chukka Boot - Men's

Now $69.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(25)
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Mix No. 6 Tavion Chukka Boot

Now $69.99
$15, $20, or $60 off!
Clearance
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Crown Vintage Shropshire Chukka Boot

Minimum Clearance Price $39.98 $39.98
★★★★★ ★★★★★
(32)
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Dr. Scholl's Sync Flex Chukka Boot

Now $74.99
$15, $20, or $60 off!
New Arrival
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Cole Haan Chamberlin Grand Chukka Boot

Now $159.99
$15, $20, or $60 off!
Clearance
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Crown Vintage Sandar Chukka Boot

Minimum Clearance Price $44.98 $44.98 – Maximum Clearance Price $59.98 $59.98
★★★★★ ★★★★★
(2)
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Florsheim Anthem Chukka Boot

$144.99
$15, $20, or $60 off!
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Florsheim Rucci Chukka Boot

Now $149.99
$15, $20, or $60 off!
Top Rated
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Carhartt Detroit Chukka Boot - Men's

$119.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(3)
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Nunn Bush Delton Chukka Boot

Now $69.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
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Carhartt Detroit Chukka Boot - Men's

$119.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
Top Rated
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Propet Findley Chukka Boot

Now $109.99 – Maximum Clearance Price $139.99 $139.99
★★★★★ ★★★★★
(47)
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
★★★★★ ★★★★★
(104)
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Florsheim Forge Plain Toe Chukka Boot

Now $114.99 – Maximum Clearance Price $129.99 $129.99
★★★★★ ★★★★★
(2)
Clearance
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Mix No. 6 Farrin Chukka Boot

Minimum Clearance Price $39.98 $39.98
★★★★★ ★★★★★
(3)
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BILLY Footwear Comfort Chukka Boot - Men's

$134.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
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Rockport Oakes Waterproof Boot

Now $119.99
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Florsheim Rucci Plain Toe Chukka Boot

Now $119.99 – Maximum Clearance Price $129.99 $129.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(5)
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Tommy Hilfiger Harbin Chukka Boot

Now $89.99
$15, $20, or $60 off!
Top Rated
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Vionic Uptown Chukka Boot

$189.99
★★★★★ ★★★★★
(10)
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Nunn Bush Briggs Chukka Boot

Now $99.99
$15, $20, or $60 off!
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Propet Kenton Chukka Boot

$147.99
★★★★★ ★★★★★
(8)
Top Rated
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TOMS Navi Chukka Boot

$144.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(15)
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Blake McKay Dixon Chukka Boot

$174.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
New Arrival
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Josef Seibel Steven 01 Boot Men's

$89.99
$15, $20, or $60 off!
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Florsheim Lodge Chukka Boot

$139.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
Clearance
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Florsheim Launch Chukka Boot

Minimum Clearance Price $84.98 $84.98
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Reaction Kenneth Cole London Chukka Boot

$118.99
$15, $20, or $60 off!
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Nunn Bush Chase Chukka Boot

Now $64.99 – Maximum Clearance Price $74.99 $74.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(5)
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Vance Stratton Boot

Now $79.99
$15, $20, or $60 off!
Clearance
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Rockport Seamus Waterproof Boot

Minimum Clearance Price $64.98 $64.98 – Maximum Clearance Price $74.98 $74.98
★★★★★ ★★★★★
(17)
New Arrival
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Steve Madden Ebner Chukka Boot

$149.99
$15, $20, or $60 off!
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HEYDUDE Bradley II Apres Boot - Men's

$79.99
New Arrival
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Steve Madden Meeker Chukka Boot

$149.99
$15, $20, or $60 off!
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Deer Stags Garfield Chukka Boot

Now $74.99
$15, $20, or $60 off!
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Florsheim Avenue Chukka Boot

$139.99
$15, $20, or $60 off!
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Kenneth Cole New York Wilhem Chukka Boot

$164.99
$15, $20, or $60 off!
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Timberland Britton Chukka Boot - Men's

$179.99
★★★★★ ★★★★★
(1)
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Caterpillar Threshold Rebound Waterproof Steel Toe Chelsea Work Boot - Men's

$144.99
$15, $20, or $60 off!
Top Rated
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Dockers Esmond Boot

Now $69.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(6)
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TOMS Carlo Mid Terrain 2.0 Sneaker - Men's

$109.99
$15, $20, or $60 off!
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
★★★★★ ★★★★★
(15)
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Rockport Works Prestige Point Work Boot

Now $154.99
★★★★★ ★★★★★
(3)
New Arrival
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Tommy Hilfiger Faltov Boot

Now $104.99
$15, $20, or $60 off!
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(6)
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Tommy Hilfiger Reesh Boot

Now $89.99
$15, $20, or $60 off!
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Fireside by Dearfoams Craft Stitch Chukka Boot

Now $97.99
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HEYDUDE Wally Mid GripR Warmth Boot - Men's

$89.99
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Stacy Adams Eastmont Chukka Boot

Now $89.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
Top Rated
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Rockport Classic Break Chukka Boot

Now $119.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(28)
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Mykos Koen Sneaker

Now $74.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
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Nunn Bush Denali Chukka Boot

Now $99.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(12)
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
$15, $20, or $60 off!
★★★★★ ★★★★★
(1)
New Arrival
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Johnston & Murphy Boswell Chukka Boot

Now $159.99
$15, $20, or $60 off!
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Tommy Hilfiger Hazmin Chukka Boot

Now $139.99
$15, $20, or $60 off!

Shop for men's chukka boots online at DSW. Search through our selection of chukkas and desert boots from top brands such as Clarks, Cole Haan, and more.