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Men's Flat Chukka Boots

70 Results

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Low Heel: 1"-2"
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70 Results
New Arrival
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Crown Vintage Patton Chukka Boot

Now $79.99
Extra 20% off reg. price!
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Clarks Shepton Chukka Boot

Minimum Clearance Price $74.98 $74.98 – Maximum Clearance Price $79.99 $79.99
★★★★★ ★★★★★
(5)
Clearance
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Crown Vintage Shropshire Chukka Boot

Minimum Clearance Price $39.98 $39.98
★★★★★ ★★★★★
(32)
New Arrival
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Timberland Auburn Falls Waterproof Chukka Boot - Men's

$139.99
★★★★★ ★★★★★
(1)
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)
Top Rated
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Nunn Bush Circuit Plain Toe Chukka Boot - Men's

Now $69.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(25)
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Nunn Bush Delton Chukka Boot

Now $69.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
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Florsheim Rucci Chukka Boot

Now $149.99
Extra 20% off reg. price!
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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 Anthem Chukka Boot

$144.99
Extra 20% off reg. price!
New Arrival
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Timberland Auburn Falls Waterproof Chukka Boot - Men's

$139.99
Top Rated
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Carhartt Detroit Chukka Boot - Men's

$119.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(3)
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Nunn Bush Briggs Chukka Boot

Now $99.99
Extra 20% off reg. price!
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BILLY Footwear Comfort Chukka Boot - Men's

$134.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
Clearance
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Mix No. 6 Farrin Chukka Boot

Minimum Clearance Price $39.98 $39.98
★★★★★ ★★★★★
(3)
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Carhartt Detroit Chukka Boot - Men's

$119.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
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Florsheim Lodge Chukka Boot

$139.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
★★★★★ ★★★★★
(104)
Top Rated
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TOMS Navi Chukka Boot

$144.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(15)
New Arrival
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Blondo Charles Waterproof Chukka Boot

$169.99
Extra 20% off reg. price!
New Arrival
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Mix No. 6 Tavion Chukka Boot

Now $69.99
Extra 20% off reg. price!
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Vance Stratton Boot

Now $79.99
Extra 20% off reg. price!
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Nunn Bush Chase Chukka Boot

Now $64.99 – Maximum Clearance Price $74.99 $74.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(4)
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Florsheim Rucci Plain Toe Chukka Boot

Now $119.99 – Maximum Clearance Price $129.99 $129.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(5)
Clearance
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Florsheim Launch Chukka Boot

Minimum Clearance Price $84.98 $84.98
Top Rated
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Vionic Uptown Chukka Boot

$189.99
★★★★★ ★★★★★
(10)
Clearance
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Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
★★★★★ ★★★★★
(15)
Clearance
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Birkenstock Uppsala Chukka Boot - Men's

Minimum Clearance Price $119.98 $119.98
★★★★★ ★★★★★
(1)
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Josef Seibel Earl 04 Chukka Boot - Men's

$179.99
Top Rated
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Dockers Esmond Boot

Now $69.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(6)
Top Rated
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Vionic Danfield Desert Boot

$209.99
★★★★★ ★★★★★
(10)
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Propet Kenton Chukka Boot

$147.99
★★★★★ ★★★★★
(8)
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Carlos by Carlos Santana Joplin Laceless Chukka Boot

Now $104.99
Extra 20% off reg. price!
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Clarks Wallaston Chukka Boot

Now $69.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(3)
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
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Nunn Bush Denali Chukka Boot

Now $99.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(12)
New Arrival
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ALDO Tomasi Chukka Boot

$149.99
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Tommy Hilfiger Voxer Chukka Boot

Now $99.00
Extra 20% off reg. price!
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Propet Findley Chukka Boot

$159.99
★★★★★ ★★★★★
(1)
Top Rated
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Eastland Seneca Chukka Boot - Men's

$119.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(6)
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(6)
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Birkenstock Uppsala Chukka Boot - Men's

$169.96
★★★★★ ★★★★★
(2)
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Anthony Veer Arden Chukka Boot

Now $299.99 – Maximum Clearance Price $348.99 $348.99
Extra 20% off reg. price!
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Timberland Britton Chukka Boot - Men's

$179.99
★★★★★ ★★★★★
(1)
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Blake McKay Dixon Chukka Boot

$174.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
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Carlos by Carlos Santana Morello Chukka Boot

Now $89.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
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Vance Austin Chukka Boot

Now $69.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(16)
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Clarks Wallaston Low Chukka Boot

Now $69.99
Extra 20% off reg. price!
Clearance
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Vince Camuto Tadesse Chukka Boot

Minimum Clearance Price $100.98 $100.98
★★★★★ ★★★★★
(4)
New Arrival
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Florsheim Avenue Chukka Boot

$139.99
Extra 20% off reg. price!
Top Rated
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Volcom Chill Work Chukka Boot - Men's

Now $114.95
★★★★★ ★★★★★
(3)
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Minnetonka Torrey Boot

$94.99
New Arrival
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Steve Madden Ebner Chukka Boot

$149.99
Extra 20% off reg. price!
New Arrival
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Steve Madden Meeker Chukka Boot

$149.99
Extra 20% off reg. price!
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Born Harrison Boot

$144.99
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Georgia Boot Athens Superlyte Waterproof Chukka Boot - Men's

Now $174.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(1)
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Bed Stu Illiad Chukka Boot - Men's

$204.99
★★★★★ ★★★★★
(1)
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Josef Seibel Erroll 52 Boot - Men's

$184.99
Top Rated
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Carlos by Carlos Santana Corazon Chukka Boot

$178.99
Extra 20% off reg. price!
★★★★★ ★★★★★
(12)
New Arrival
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Sperry Minilug Chukka Boot

$149.99