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  1. Boots

Men's Chukka Boots

99 Results
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
BOGO 50% off
★★★★★ ★★★★★
(100)
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Clarks Shepton Chukka Boot

Minimum Clearance Price $74.98 $74.98 – Maximum Clearance Price $94.99 $94.99
BOGO 50% off
★★★★★ ★★★★★
(4)
Clearance
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Crown Vintage Shropshire Chukka Boot

Minimum Clearance Price $44.98 $44.98
BOGO 50% off
★★★★★ ★★★★★
(32)
Clearance
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Mix No. 6 Farrin Chukka Boot

Minimum Clearance Price $39.98 $39.98
BOGO 50% off
★★★★★ ★★★★★
(3)
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
BOGO 50% off
★★★★★ ★★★★★
(68)
Clearance
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Clarks Wallaston Chukka Boot

$69.99 – Maximum Clearance Price $74.98 $74.98
BOGO 50% off
★★★★★ ★★★★★
(3)
Clearance
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Florsheim Rucci Plain Toe Chukka Boot

Minimum Clearance Price $104.98 $104.98 – Maximum Clearance Price $119.99 $119.99
BOGO 50% off
★★★★★ ★★★★★
(4)
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Florsheim Lodge Chukka Boot

$139.99
BOGO 50% off
Top Rated
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Propet Findley Chukka Boot

Now $109.99 – Maximum Clearance Price $139.99 $139.99
BOGO 1st pair only
★★★★★ ★★★★★
(46)
Top Rated
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Nunn Bush Circuit Plain Toe Chukka Boot - Men's

Now $69.99
BOGO 50% off
★★★★★ ★★★★★
(25)
Top Rated
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Rockport Classic Break Chukka Boot

Now $119.99
BOGO 50% off
★★★★★ ★★★★★
(28)
Clearance
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Crown Vintage Sandar Chukka Boot

Minimum Clearance Price $49.98 $49.98 – Maximum Clearance Price $59.98 $59.98
BOGO 50% off
★★★★★ ★★★★★
(2)
Clearance
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Florsheim Launch Chukka Boot

Minimum Clearance Price $89.98 $89.98
BOGO 50% off
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Stacy Adams Eastmont Chukka Boot

Now $99.99
BOGO 50% off
★★★★★ ★★★★★
(1)
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Vance Stratton Boot

Now $79.99
BOGO 50% off
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Clarks Wallaston Low Chukka Boot

Now $69.99
BOGO 50% off
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Nunn Bush Chase Chukka Boot

Now $64.99 – Maximum Clearance Price $74.99 $74.99
BOGO 50% off
★★★★★ ★★★★★
(3)
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Florsheim Anthem Chukka Boot

$144.99
BOGO 50% off
Clearance
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Birkenstock Uppsala Chukka Boot - Men's

Clearance Item - Add to bag to see price Add to bag to see price
BOGO 1st pair only
★★★★★ ★★★★★
(2)
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Reaction Kenneth Cole Vesto Boot

Now $89.99
BOGO 50% off
★★★★★ ★★★★★
(1)
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Kenneth Cole New York Wilhem Chukka Boot

$164.99
BOGO 50% off
Clearance
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Rockport Seamus Waterproof Boot

Minimum Clearance Price $79.98 $79.98
BOGO 1st pair only
★★★★★ ★★★★★
(17)
Top Rated
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Carhartt Detroit Chukka Boot - Men's

$119.99
BOGO 50% off
★★★★★ ★★★★★
(3)
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Clarks Weltridge Boot

$119.99
BOGO 50% off
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Nunn Bush Delton Chukka Boot

Now $69.99
BOGO 50% off
★★★★★ ★★★★★
(1)
Clearance
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Birkenstock Uppsala Chukka Boot - Men's

Minimum Clearance Price $139.98 $139.98
BOGO 1st pair only
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Carlos by Carlos Santana Morello Chukka Boot

Now $89.99
BOGO 50% off
★★★★★ ★★★★★
(1)
Top Rated
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Rockport Weather Or Not Waterproof Work Chukka Boot - Men's

Now $119.99
BOGO 1st pair only
★★★★★ ★★★★★
(254)
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Vance Austin Chukka Boot

Now $64.99
BOGO 50% off
★★★★★ ★★★★★
(15)
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Bed Stu Illiad Chukka Boot - Men's

$204.99
BOGO 1st pair only
★★★★★ ★★★★★
(1)
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Carlos by Carlos Santana Corazon Chukka Boot

Now $107.99 – Maximum Clearance Price $178.99 $178.99
BOGO 50% off
★★★★★ ★★★★★
(6)
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Carhartt Haslett Moc Toe Boot - Men's

$104.99
BOGO 50% off
★★★★★ ★★★★★
(41)
Top Rated
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Dockers Esmond Boot

Now $69.99
BOGO 50% off
★★★★★ ★★★★★
(6)
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Blake McKay Dixon Chukka Boot

$174.99
BOGO 50% off
★★★★★ ★★★★★
(1)
Top Rated
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Eastland Jack Chukka Boot - Men's

Now $119.99
BOGO 50% off
★★★★★ ★★★★★
(5)
Clearance
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Crown Vintage Gaspen Chukka Boot

Minimum Clearance Price $29.98 $29.98
BOGO 50% off
★★★★★ ★★★★★
(55)
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Anthony Veer Arden Chukka Boot

Now $284.99 – Maximum Clearance Price $299.99 $299.99
BOGO 50% off
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Rustic Asphalt Corn Stalk Chukka Boot

$88.99
BOGO 50% off
★★★★★ ★★★★★
(34)
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Clarks Steadwall Mid Chukka Boot

Now $89.99
BOGO 50% off
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Carhartt Detroit Chukka Boot - Men's

$119.99
BOGO 50% off
★★★★★ ★★★★★
(1)
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BILLY Footwear Comfort Chukka Boot - Men's

$134.99
BOGO 50% off
★★★★★ ★★★★★
(1)
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Territory Axel Boot

Now $49.99
BOGO 50% off
★★★★★ ★★★★★
(12)
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Anthony Veer George Chukka Boot

Now $99.99
BOGO 50% off
★★★★★ ★★★★★
(2)
Top Rated
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Clarks Shacre Chukka Boot

Now $89.99
BOGO 50% off
★★★★★ ★★★★★
(73)
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Nunn Bush Denali Chukka Boot

Now $99.99
BOGO 50% off
★★★★★ ★★★★★
(12)
Clearance
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Vince Camuto Tadesse Chukka Boot

Minimum Clearance Price $100.98 $100.98
BOGO 50% off
★★★★★ ★★★★★
(4)
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Territory Redwoods Chukka Boot

Now $44.99
BOGO 50% off
★★★★★ ★★★★★
(1)
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Clarks Walpath Chukka Boot

$119.99
BOGO 50% off
Clearance
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Crown Vintage Jalynn Chukka Boot

Minimum Clearance Price $64.98 $64.98
BOGO 50% off
★★★★★ ★★★★★
(18)
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Propet Findley Chukka Boot

$159.99
BOGO 1st pair only
★★★★★ ★★★★★
(1)
Top Rated
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Vionic Danfield Desert Boot

$209.99
BOGO 1st pair only
★★★★★ ★★★★★
(8)
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Propet Kenton Chukka Boot

$147.99
BOGO 1st pair only
★★★★★ ★★★★★
(8)
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Florsheim Forge Plain Toe Chukka Boot

Now $114.99 – Maximum Clearance Price $129.99 $129.99
BOGO 1st pair only
★★★★★ ★★★★★
(2)
Top Rated
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Vionic Uptown Chukka Boot

$189.99
BOGO 1st pair only
★★★★★ ★★★★★
(7)
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Caterpillar Threshold Rebound Waterproof Steel Toe Chelsea Work Boot - Men's

$144.99
BOGO 50% off
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Born Harrison Boot

$144.99
BOGO 1st pair only
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Minnetonka Torrey Boot

$94.99
BOGO 1st pair only
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Mykos Koen Sneaker

Now $74.99
BOGO 50% off
★★★★★ ★★★★★
(1)
Clearance
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Clarks Bushacre 3 Chukka Boot

Minimum Clearance Price $74.98 $74.98
BOGO 50% off
★★★★★ ★★★★★
(196)
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Rockport Works Prestige Point Work Boot

Now $139.99
BOGO 1st pair only
★★★★★ ★★★★★
(2)

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.