Filters

Get it Fast
Get it Fast
101 Results
  1. Home
    /
  2. Men's
    /
  3. Men's Shoes
    /
  4. Boots
    /
  5. Chukka
  1. Boots
  1. Home
    /
  2. Men's
    /
  3. Men's Shoes
    /
  4. Boots
    /
  5. Chukka
  1. Boots

Men's Chukka Boots

101 Results
Clearance
product image

Crown Vintage Shropshire Chukka Boot

Minimum Clearance Price $44.98 $44.98
★★★★★ ★★★★★
(32)
Clearance
product image

Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
★★★★★ ★★★★★
(100)
product image

Clarks Shepton Chukka Boot

Minimum Clearance Price $74.98 $74.98 – Maximum Clearance Price $94.99 $94.99
★★★★★ ★★★★★
(4)
Clearance
product image

Mix No. 6 Farrin Chukka Boot

Minimum Clearance Price $39.98 $39.98
★★★★★ ★★★★★
(3)
Top Rated
product image

Propet Findley Chukka Boot

Now $109.99 – Maximum Clearance Price $139.99 $139.99
★★★★★ ★★★★★
(46)
Clearance
product image

Timberland Westmore Chukka Boot - Men's

Minimum Clearance Price $79.98 $79.98
★★★★★ ★★★★★
(68)
Clearance
product image

Clarks Wallaston Chukka Boot

$69.99 – Maximum Clearance Price $74.98 $74.98
★★★★★ ★★★★★
(3)
Top Rated
product image

Rockport Classic Break Chukka Boot

Now $119.99
★★★★★ ★★★★★
(28)
Clearance
product image

Florsheim Rucci Plain Toe Chukka Boot

Minimum Clearance Price $104.98 $104.98 – Maximum Clearance Price $119.99 $119.99
★★★★★ ★★★★★
(4)
Top Rated
product image

Nunn Bush Circuit Plain Toe Chukka Boot - Men's

Now $69.99
★★★★★ ★★★★★
(25)
product image

Florsheim Lodge Chukka Boot

$139.99
Clearance
product image

Florsheim Launch Chukka Boot

Minimum Clearance Price $89.98 $89.98
product image

Clarks Weltridge Boot

$119.99
product image

Vance Stratton Boot

Now $79.99
Clearance
product image

Crown Vintage Sandar Chukka Boot

Minimum Clearance Price $49.98 $49.98 – Maximum Clearance Price $59.98 $59.98
★★★★★ ★★★★★
(2)
product image

BILLY Footwear Comfort Chukka Boot - Men's

$134.99
★★★★★ ★★★★★
(1)
product image

Clarks Wallaston Low Chukka Boot

Now $69.99
Clearance
product image

Rockport Seamus Waterproof Boot

Minimum Clearance Price $79.98 $79.98
★★★★★ ★★★★★
(17)
product image

Nunn Bush Chase Chukka Boot

Now $64.99 – Maximum Clearance Price $74.99 $74.99
★★★★★ ★★★★★
(3)
product image

Kenneth Cole New York Wilhem Chukka Boot

$164.99
Clearance
product image

Birkenstock Uppsala Chukka Boot - Men's

Clearance Item - Add to bag to see price Add to bag to see price
★★★★★ ★★★★★
(2)
product image

Florsheim Anthem Chukka Boot

$144.99
product image

Reaction Kenneth Cole Vesto Boot

Now $89.99
★★★★★ ★★★★★
(1)
product image

Stacy Adams Eastmont Chukka Boot

Now $99.99
New Lower Price!
★★★★★ ★★★★★
(1)
Top Rated
product image

Carhartt Detroit Chukka Boot - Men's

$119.99
★★★★★ ★★★★★
(3)
product image

Nunn Bush Delton Chukka Boot

Now $69.99
★★★★★ ★★★★★
(1)
Clearance
product image

Birkenstock Uppsala Chukka Boot - Men's

Minimum Clearance Price $139.98 $139.98
product image

Blake McKay Dixon Chukka Boot

$174.99
★★★★★ ★★★★★
(1)
product image

Vance Austin Chukka Boot

Now $64.99
★★★★★ ★★★★★
(15)
Top Rated
product image

Dockers Esmond Boot

Now $69.99
★★★★★ ★★★★★
(6)
product image

Carlos by Carlos Santana Morello Chukka Boot

Now $89.99
★★★★★ ★★★★★
(1)
Top Rated
product image

Eastland Jack Chukka Boot - Men's

Now $119.99
★★★★★ ★★★★★
(5)
product image

Carhartt Detroit Chukka Boot - Men's

$119.99
★★★★★ ★★★★★
(1)
Top Rated
product image

Rockport Weather Or Not Waterproof Work Chukka Boot - Men's

Now $119.99
★★★★★ ★★★★★
(254)
product image

Bed Stu Illiad Chukka Boot - Men's

$204.99
★★★★★ ★★★★★
(1)
product image

Anthony Veer Arden Chukka Boot

Now $284.99 – Maximum Clearance Price $299.99 $299.99
product image

Carhartt Haslett Moc Toe Boot - Men's

$104.99
★★★★★ ★★★★★
(41)
product image

Carlos by Carlos Santana Corazon Chukka Boot

Now $107.99 – Maximum Clearance Price $178.99 $178.99
★★★★★ ★★★★★
(6)
product image

Anthony Veer George Chukka Boot

Now $99.99
★★★★★ ★★★★★
(2)
product image

Clarks Steadwall Mid Chukka Boot

Now $89.99
product image

Eastland Seneca Chukka Boot - Men's

$119.99
product image

Rustic Asphalt Corn Stalk Chukka Boot

$88.99
★★★★★ ★★★★★
(34)
Clearance
product image

Crown Vintage Gaspen Chukka Boot

Minimum Clearance Price $29.98 $29.98
★★★★★ ★★★★★
(55)
Top Rated
product image

Clarks Shacre Chukka Boot

Now $89.99
★★★★★ ★★★★★
(72)
product image

Nunn Bush Denali Chukka Boot

Now $99.99
★★★★★ ★★★★★
(12)
product image

Territory Axel Boot

Now $49.99
★★★★★ ★★★★★
(12)
product image

Clarks Walpath Chukka Boot

$119.99
product image

Propet Findley Chukka Boot

$159.99
★★★★★ ★★★★★
(1)
Top Rated
product image

Vionic Danfield Desert Boot

$209.99
★★★★★ ★★★★★
(8)
product image

Propet Kenton Chukka Boot

$147.99
★★★★★ ★★★★★
(8)
product image

Florsheim Forge Plain Toe Chukka Boot

Now $114.99 – Maximum Clearance Price $129.99 $129.99
★★★★★ ★★★★★
(2)
Top Rated
product image

Vionic Uptown Chukka Boot

$189.99
★★★★★ ★★★★★
(7)
product image

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

$144.99
product image

Territory Redwoods Chukka Boot

Now $44.99
★★★★★ ★★★★★
(1)
Clearance
product image

Crown Vintage Jalynn Chukka Boot

Minimum Clearance Price $64.98 $64.98
★★★★★ ★★★★★
(18)
product image

Born Harrison Boot

$144.99
product image

Minnetonka Torrey Boot

$94.99
product image

Mykos Koen Sneaker

Now $74.99
★★★★★ ★★★★★
(1)
Clearance
product image

Clarks Bushacre 3 Chukka Boot

Minimum Clearance Price $74.98 $74.98
★★★★★ ★★★★★
(196)
product image

Clarks Radcliff Mid Boot

Now $94.99

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.