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Men's Chukka Boots

103 Results

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103 Results
New Arrival
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Rockport Merrick Waterproof Boot

Now $119.99
BOGO 1st pair only!
New Arrival
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Crown Vintage Patton Chukka Boot

Now $79.99
BOGO 50% off!
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Clarks Shepton Chukka Boot

Minimum Clearance Price $74.98 $74.98 – Maximum Clearance Price $79.99 $79.99
BOGO 50% off!
★★★★★ ★★★★★
(5)
Clearance
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Crown Vintage Shropshire Chukka Boot

Minimum Clearance Price $39.98 $39.98
BOGO 50% off!
★★★★★ ★★★★★
(32)
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Dr. Scholl's Sync Flex Chukka Boot

Now $54.99
Limited time! Up to 40% 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
BOGO 50% off!
★★★★★ ★★★★★
(2)
New Arrival
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Timberland Auburn Falls Waterproof Chukka Boot - Men's

$139.99
BOGO 1st pair only!
Clearance
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Mix No. 6 Farrin Chukka Boot

Minimum Clearance Price $39.98 $39.98
BOGO 50% off!
★★★★★ ★★★★★
(3)
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Nunn Bush Delton Chukka Boot

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(1)
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Nunn Bush Briggs Chukka Boot

Now $99.99
BOGO 50% off!
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Florsheim Anthem Chukka Boot

$144.99
BOGO 50% off!
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Florsheim Rucci Chukka Boot

Now $149.99
BOGO 50% off!
Top Rated
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Nunn Bush Circuit Plain Toe Chukka Boot - Men's

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(25)
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
BOGO 1st pair only!
★★★★★ ★★★★★
(104)
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Rockport Oakes Waterproof Boot

Now $119.99
BOGO 1st pair only!
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Carhartt Detroit Chukka Boot - Men's

$119.99
BOGO 50% off!
★★★★★ ★★★★★
(1)
New Arrival
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Timberland Auburn Falls Waterproof Chukka Boot - Men's

$139.99
BOGO 1st pair only!
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Florsheim Lodge Chukka Boot

$139.99
BOGO 50% off!
★★★★★ ★★★★★
(1)
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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)
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Tommy Hilfiger Harbin Chukka Boot

Now $89.99
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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Carhartt Detroit Chukka Boot - Men's

$119.99
BOGO 50% off!
★★★★★ ★★★★★
(3)
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BILLY Footwear Comfort Chukka Boot - Men's

$134.99
BOGO 50% off!
★★★★★ ★★★★★
(1)
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Vance Stratton Boot

Now $79.99
BOGO 50% off!
Top Rated
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TOMS Navi Chukka Boot

$144.99
BOGO 50% off!
★★★★★ ★★★★★
(15)
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Stacy Adams Eastmont Chukka Boot

Now $89.99
BOGO 50% off!
★★★★★ ★★★★★
(1)
Clearance
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Florsheim Launch Chukka Boot

Minimum Clearance Price $84.98 $84.98
BOGO 50% off!
New Arrival
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Tommy Hilfiger Faltov Boot

Now $104.99
BOGO 50% off!
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Reaction Kenneth Cole London Chukka Boot

$118.99
BOGO 50% off!
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Florsheim Rucci Plain Toe Chukka Boot

Now $119.99 – Maximum Clearance Price $129.99 $129.99
BOGO 50% off!
★★★★★ ★★★★★
(5)
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Nunn Bush Chase Chukka Boot

Now $64.99 – Maximum Clearance Price $74.99 $74.99
BOGO 50% off!
★★★★★ ★★★★★
(4)
Clearance
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Birkenstock Uppsala Chukka Boot - Men's

Minimum Clearance Price $119.98 $119.98
BOGO 1st pair only!
★★★★★ ★★★★★
(1)
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Reaction Kenneth Cole Vesto Boot

Now $89.99
BOGO 50% off!
★★★★★ ★★★★★
(1)
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Tommy Hilfiger Hazmin Chukka Boot

Now $139.99
BOGO 50% off!
Clearance
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Rockport Seamus Waterproof Boot

Minimum Clearance Price $64.98 $64.98 – Maximum Clearance Price $74.98 $74.98
BOGO 1st pair only!
★★★★★ ★★★★★
(17)
New Arrival
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Mix No. 6 Tavion Chukka Boot

Now $69.99
BOGO 50% off!
New Arrival
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Tommy Hilfiger Reesh Boot

Now $89.99
BOGO 50% off!
New Arrival
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Blondo Charles Waterproof Chukka Boot

$169.99
BOGO 50% off!
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HEYDUDE Bradley II Apres Boot - Men's

$79.99
BOGO 1st pair only!
New Arrival
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Florsheim Avenue Chukka Boot

$139.99
BOGO 50% off!
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Deer Stags Garfield Chukka Boot

Now $74.99
BOGO 50% off!
Top Rated
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Vionic Danfield Desert Boot

$209.99
BOGO 1st pair only!
★★★★★ ★★★★★
(10)
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Rockport Works Prestige Point Work Boot

Now $154.99
BOGO 1st pair only!
★★★★★ ★★★★★
(3)
New Arrival
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Tommy Hilfiger Favy Chukka Boot

Now $134.99
BOGO 50% off!
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Carlos by Carlos Santana Joplin Laceless Chukka Boot

Now $104.99
BOGO 50% off!
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Caterpillar Threshold Rebound Waterproof Steel Toe Chelsea Work Boot - Men's

$144.99
BOGO 50% off!
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
BOGO 1st pair only!
★★★★★ ★★★★★
(15)
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Clarks Wallaston Chukka Boot

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(3)
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Propet Kenton Chukka Boot

$147.99
BOGO 1st pair only!
★★★★★ ★★★★★
(8)
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
BOGO 50% off!
★★★★★ ★★★★★
(1)
Top Rated
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Dockers Esmond Boot

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(6)
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Josef Seibel Earl 04 Chukka Boot - Men's

$179.99
BOGO 1st pair only!
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Propet Findley Chukka Boot

$159.99
BOGO 1st pair only!
★★★★★ ★★★★★
(1)
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TOMS Carlo Mid Terrain 2.0 Sneaker - Men's

$109.99
BOGO 50% off!
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HEYDUDE Wally Mid GripR Warmth Boot - Men's

$89.99
BOGO 1st pair only!
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Nunn Bush Denali Chukka Boot

Now $99.99
BOGO 50% off!
★★★★★ ★★★★★
(12)
New Arrival
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Sperry Minilug Chukka Boot

$149.99
BOGO 50% off!
Top Rated
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Rockport Classic Break Chukka Boot

Now $119.99
BOGO 50% off!
★★★★★ ★★★★★
(28)
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Tommy Hilfiger Voxer Chukka Boot

Now $99.00
BOGO 50% off!
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Vance Austin Chukka Boot

Now $69.99
BOGO 50% off!
★★★★★ ★★★★★
(16)

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.