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  5. Chukka
  1. Boots

Men's Chukka Boots

105 Results
Top Rated
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Timberland Westmore Chukka Boot - Men's

$99.99
★★★★★ ★★★★★
(98)
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Clarks Shepton Chukka Boot

Minimum Clearance Price $74.98 $74.98 – Maximum Clearance Price $94.99 $94.99
★★★★★ ★★★★★
(3)
Clearance
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Crown Vintage Shropshire Chukka Boot

Minimum Clearance Price $44.98 $44.98
★★★★★ ★★★★★
(30)
Clearance
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Mix No. 6 Farrin Chukka Boot

Minimum Clearance Price $44.98 $44.98
★★★★★ ★★★★★
(2)
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Florsheim Rucci Plain Toe Chukka Boot

Now $119.99 – Maximum Clearance Price $129.99 $129.99
★★★★★ ★★★★★
(4)
Clearance
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Crown Vintage Sandar Chukka Boot

Minimum Clearance Price $54.98 $54.98 – Maximum Clearance Price $59.98 $59.98
★★★★★ ★★★★★
(2)
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Clarks Wallaston Chukka Boot

Now $69.99 – Maximum Clearance Price $89.99 $89.99
★★★★★ ★★★★★
(2)
Top Rated
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Rockport Classic Break Chukka Boot

Now $119.99
★★★★★ ★★★★★
(28)
Top Rated
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Nunn Bush Circuit Plain Toe Chukka Boot - Men's

Now $69.99
★★★★★ ★★★★★
(25)
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Timberland Westmore Chukka Boot - Men's

$99.99
★★★★★ ★★★★★
(66)
Clearance
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Florsheim Launch Chukka Boot

Minimum Clearance Price $104.98 $104.98
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Clarks Weltridge Boot

$119.99
Top Rated
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Carhartt Detroit Chukka Boot - Men's

$119.99
★★★★★ ★★★★★
(3)
Clearance
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Rockport Seamus Waterproof Boot

Minimum Clearance Price $84.98 $84.98 – Maximum Clearance Price $89.98 $89.98
★★★★★ ★★★★★
(15)
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Florsheim Forge Plain Toe Chukka Boot

Now $114.99 – Maximum Clearance Price $129.99 $129.99
★★★★★ ★★★★★
(2)
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Vance Stratton Boot

Now $79.99
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Florsheim Lodge Chukka Boot

$139.99
Top Rated
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Propet Findley Chukka Boot

$109.99 – Maximum Clearance Price $139.99 $139.99
★★★★★ ★★★★★
(45)
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Stacy Adams Eastmont Chukka Boot

Now $99.99
★★★★★ ★★★★★
(1)
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Kenneth Cole New York Wilhem Chukka Boot

$164.99
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Nunn Bush Chase Chukka Boot

Now $64.99 – Maximum Clearance Price $74.99 $74.99
★★★★★ ★★★★★
(3)
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BILLY Footwear Comfort Chukka Boot - Men's

$134.99
★★★★★ ★★★★★
(1)
Top Rated
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Rockport Weather Or Not Waterproof Work Chukka Boot - Men's

Now $119.99
★★★★★ ★★★★★
(254)
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Clarks Steadwall Mid Chukka Boot

Now $89.99
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Carhartt Haslett Moc Toe Boot - Men's

$104.99
★★★★★ ★★★★★
(41)
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Born Harrison Boot

$144.99
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Carhartt Detroit Chukka Boot - Men's

$119.99
★★★★★ ★★★★★
(1)
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Nunn Bush Delton Chukka Boot

Now $69.99
★★★★★ ★★★★★
(1)
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Propet Findley Chukka Boot

$159.99
★★★★★ ★★★★★
(1)
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Florsheim Anthem Chukka Boot

$144.99
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Deer Stags Garfield Chukka Boot

Now $64.99 – Maximum Clearance Price $69.99 $69.99
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Vintage Foundry Milton Chukka Boot

Now $104.99
★★★★★ ★★★★★
(1)
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Thomas & Vine Banks Chukka Boot

Now $49.99
★★★★★ ★★★★★
(1)
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Carlos by Carlos Santana Joplin Laceless Chukka Boot

Now $104.99
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Blake McKay Dixon Chukka Boot

$174.99
★★★★★ ★★★★★
(1)
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Minnetonka Torrey Boot

$94.99
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Vance Austin Chukka Boot

Now $64.99
★★★★★ ★★★★★
(15)
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Rockport Works Prestige Point Work Boot

Now $139.99
★★★★★ ★★★★★
(2)
Clearance
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Thomas & Vine Keegan Chukka Boot

Now $79.99
★★★★★ ★★★★★
(6)
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Bed Stu Illiad Chukka Boot - Men's

$204.99
★★★★★ ★★★★★
(1)
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Carlos by Carlos Santana Morello Chukka Boot

Now $89.99
★★★★★ ★★★★★
(1)
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Anthony Veer Arden Chukka Boot

Now $284.99 – Maximum Clearance Price $299.99 $299.99
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Birkenstock Uppsala Chukka Boot - Men's

$169.96
★★★★★ ★★★★★
(2)
Top Rated
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Dockers Esmond Boot

Now $69.99
★★★★★ ★★★★★
(6)
Top Rated
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Clarks Shacre Chukka Boot

Now $89.99
★★★★★ ★★★★★
(72)
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Anthony Veer Heritage Chukka Boot

Now $324.99
Clearance
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Crown Vintage Jalynn Chukka Boot

Minimum Clearance Price $64.98 $64.98
★★★★★ ★★★★★
(18)
Top Rated
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Territory Bridger Boot

Now $49.99 – Maximum Clearance Price $59.99 $59.99
★★★★★ ★★★★★
(15)
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Nunn Bush Denali Chukka Boot

Now $99.99
★★★★★ ★★★★★
(12)
Clearance
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Clarks Bushacre 3 Chukka Boot

Minimum Clearance Price $74.98 $74.98
★★★★★ ★★★★★
(196)
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
★★★★★ ★★★★★
(5)
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Eastland Seneca Chukka Boot - Men's

$119.99
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Bruno Magli Primo Chukka Boot

$149.99
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Reaction Kenneth Cole Vesto Boot

$118.99
★★★★★ ★★★★★
(1)
Clearance
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Calvin Klein Javin Chukka Boot

Minimum Clearance Price $97.98 $97.98
★★★★★ ★★★★★
(1)
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Propet Kenton Chukka Boot

$147.99
★★★★★ ★★★★★
(8)
Top Rated
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Vionic Danfield Desert Boot

$209.99
★★★★★ ★★★★★
(8)
Top Rated
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Vionic Uptown Chukka Boot

$189.99
★★★★★ ★★★★★
(5)
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Caterpillar Threshold Rebound Waterproof Steel Toe Chelsea Work Boot - Men's

$144.99
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Mykos Koen Sneaker

Now $74.99
★★★★★ ★★★★★
(1)

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.