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  5. Chukka
  1. Boots

Men's Chukka Boots

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

$99.99
★★★★★ ★★★★★
(91)
Top Rated
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Crown Vintage Shropshire Chukka Boot

Now $79.99
★★★★★ ★★★★★
(29)
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Clarks Shepton Chukka Boot

Now $94.99
★★★★★ ★★★★★
(2)
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Clarks Wallaston Chukka Boot

Now $69.99 – Maximum Clearance Price $89.99 $89.99
Up to 50% Off!
★★★★★ ★★★★★
(2)
Clearance
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Crown Vintage Sandar Chukka Boot

Minimum Clearance Price $59.98 $59.98
Up to 50% Off!
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Timberland Westmore Chukka Boot - Men's

$99.99
★★★★★ ★★★★★
(63)
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Mix No. 6 Farrin Chukka Boot

Now $59.99
★★★★★ ★★★★★
(1)
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Clarks Weltridge Boot

$119.99
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Deer Stags Garfield Chukka Boot

Now $64.99 – Maximum Clearance Price $69.99 $69.99
Clearance
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Rockport Seamus Waterproof Boot

Minimum Clearance Price $89.98 $89.98
★★★★★ ★★★★★
(14)
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Nunn Bush Chase Chukka Boot

Now $64.99 – Maximum Clearance Price $74.99 $74.99
★★★★★ ★★★★★
(3)
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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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Florsheim Rucci Plain Toe Chukka Boot

Now $119.99 – Maximum Clearance Price $129.99 $129.99
★★★★★ ★★★★★
(4)
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Carhartt Detroit Chukka Boot - Men's

Now $109.99
★★★★★ ★★★★★
(1)
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Vance Stratton Boot

Now $79.99
New Arrival
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Clarks Wallaston Low Chukka Boot

Now $69.99
Top Rated
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Propet Findley Chukka Boot

$109.99 – Maximum Clearance Price $139.99 $139.99
★★★★★ ★★★★★
(44)
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Nunn Bush Delton Chukka Boot

Now $69.99
★★★★★ ★★★★★
(1)
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Vance Austin Chukka Boot

Now $64.99
Up to 50% Off!
★★★★★ ★★★★★
(15)
Top Rated
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Rockport Weather Or Not Waterproof Work Chukka Boot

Now $119.99
★★★★★ ★★★★★
(254)
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Florsheim Anthem Chukka Boot

$144.99
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Stacy Adams Eastmont Chukka Boot

Now $99.99
Up to 50% Off!
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Carhartt Haslett Moc Toe Boot - Men's

Now $99.99
★★★★★ ★★★★★
(39)
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Clarks Steadwall Mid Chukka Boot

Now $89.99
Up to 50% Off!
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Carhartt Detroit Chukka Boot - Men's

Now $109.99
★★★★★ ★★★★★
(1)
Top Rated
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Nunn Bush Circuit Plain Toe Chukka Boot - Men's

Now $69.99
★★★★★ ★★★★★
(23)
Top Rated
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Rockport Classic Break Chukka Boot

Now $119.99
★★★★★ ★★★★★
(27)
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Florsheim Launch Chukka Boot

Now $129.99
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Born Harrison Boot

$144.99
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Reaction Kenneth Cole Vesto Boot

$118.99
Top Rated
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TOMS Navi Chukka Boot

$144.99
★★★★★ ★★★★★
(15)
Top Rated
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Territory Bridger Boot

Now $49.99 – Maximum Clearance Price $59.99 $59.99
★★★★★ ★★★★★
(15)
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Kenneth Cole New York Wilhem Chukka Boot

$164.99
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Florsheim Lodge Chukka Boot

$139.99
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Vintage Foundry Milton Chukka Boot

Now $104.99
★★★★★ ★★★★★
(1)
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Dansko Tony Chukka Boot

$194.99
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Caterpillar Threshold Rebound Waterproof Steel Toe Chelsea Work Boot - Men's

$144.99
Clearance
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Crown Vintage Jalynn Chukka Boot

Minimum Clearance Price $64.98 $64.98
★★★★★ ★★★★★
(18)
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Blake McKay Dixon Chukka Boot

$174.99
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Propet Findley Chukka Boot

$159.99
★★★★★ ★★★★★
(1)
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Vintage Foundry Marlow Chukka Boot

Now $199.99
★★★★★ ★★★★★
(1)
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Clarks Radcliff Mid Boot

Now $94.99
Clearance
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Clarks Bushacre 3 Chukka Boot

Minimum Clearance Price $62.98 $62.98 – Maximum Clearance Price $74.98 $74.98
★★★★★ ★★★★★
(196)
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Nunn Bush Denali Chukka Boot

Now $99.99
★★★★★ ★★★★★
(12)
Top Rated
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
★★★★★ ★★★★★
(11)
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Steve Madden Harken Chukka Boot

$109.99
★★★★★ ★★★★★
(8)
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Birkenstock Uppsala Chukka Boot - Men's

$169.96
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TOMS Carlo Mid Terrain 2.0 Sneaker - Men's

$109.99
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Sperry Mini Lug Chukka Boot

$149.99
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Rockport Works Prestige Point Work Boot

Now $139.99
★★★★★ ★★★★★
(1)
Top Rated
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Dockers Esmond Boot

Now $69.99
★★★★★ ★★★★★
(4)
Clearance
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Thomas & Vine Keegan Chukka Boot

Now $79.99
★★★★★ ★★★★★
(6)
Clearance
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Clarks Eastridge Chukka Boot

Minimum Clearance Price $62.98 $62.98
Up to 50% Off!
★★★★★ ★★★★★
(33)
Top Rated
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Eastland Seneca Chukka Boot - Men's

$119.99
★★★★★ ★★★★★
(7)
Clearance
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Vince Camuto Tadesse Chukka Boot

Minimum Clearance Price $100.98 $100.98
★★★★★ ★★★★★
(4)
Top Rated
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Clarks Shacre Chukka Boot

Now $89.99
Up to 50% Off!
★★★★★ ★★★★★
(71)
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Born Brock Chukka Boot

$149.99
Clearance
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Calvin Klein Javin Chukka Boot

Minimum Clearance Price $97.98 $97.98
★★★★★ ★★★★★
(1)
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Thomas & Vine Banks Chukka Boot

Now $49.99
★★★★★ ★★★★★
(1)
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BILLY Footwear Comfort Chukka Boot - Men's

$134.99
★★★★★ ★★★★★
(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.