Shop Fashion Chukka Boots for Men

Sponsored
$69.98
$79.99
Men's Freeman Brent Chukka Boot In Tan Size 8.5
Shoe Carnival
$10 Off*
12% off
$69.98
$79.99
Men's Freeman Brent Chukka Boot In Tan Size 8.5
Shoe Carnival
$10 Off*
$54.98
$89.99
Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 11.5
Shoe Carnival
$10 Off*
38% off
$54.98
$89.99
Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 11.5
Shoe Carnival
$10 Off*
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Brown Size 13
Shoe Carnival
$10 Off*
25% off
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Brown Size 13
Shoe Carnival
$10 Off*
$34.98
$44.99
Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 8
Shoe Carnival
$10 Off*
22% off
$34.98
$44.99
Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 8
Shoe Carnival
$10 Off*
$34.98
$44.99
Men's Reserved Footwear Petrus Chukka Dress Boot In Black Size 8
Shoe Carnival
$10 Off*
22% off
$34.98
$44.99
Men's Reserved Footwear Petrus Chukka Dress Boot In Black Size 8
Shoe Carnival
$10 Off*
$74.98
$99.99
Men's Reserved Footwear Palmetto Chukka Dress Boot In Brown Size 10.5
Shoe Carnival
$10 Off*
25% off
$74.98
$99.99
Men's Reserved Footwear Palmetto Chukka Dress Boot In Brown Size 10.5
Shoe Carnival
$10 Off*
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Dark Tan Size 8.5
Shoe Carnival
$10 Off*
25% off
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Dark Tan Size 8.5
Shoe Carnival
$10 Off*
$74.98
$94.99
Men's Dockers Calgary Chukka Boot Oxfords In Taupe Size 12
Shoe Carnival
$10 Off*
21% off
$74.98
$94.99
Men's Dockers Calgary Chukka Boot Oxfords In Taupe Size 12
Shoe Carnival
$10 Off*
$49.98
$59.99
Men's New York And Company Kevin Chukka Dress Boot In Cognac Size 9
Shoe Carnival
$10 Off*
16% off
$49.98
$59.99
Men's New York And Company Kevin Chukka Dress Boot In Cognac Size 9
Shoe Carnival
$10 Off*
$89.98
$119.99
Men's Vintage Foundry Co Lewis Dress Chukka Boot In Brown Size 8
Shoe Carnival
$10 Off*
25% off
$89.98
$119.99
Men's Vintage Foundry Co Lewis Dress Chukka Boot In Brown Size 8
Shoe Carnival
$10 Off*
$119.98
$124.99
Men's Stacy Adams Maxwell Chukka Boot In Cognac Size 11
Shoe Carnival
$10 Off*
$119.98
$124.99
Men's Stacy Adams Maxwell Chukka Boot In Cognac Size 11
Shoe Carnival
$10 Off*
$119.98
$129.99
Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5
Shoe Carnival
$10 Off*
$119.98
$129.99
Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5
Shoe Carnival
$10 Off*
$109.98
$114.99
Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 13
Shoe Carnival
$10 Off*
$109.98
$114.99
Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 13
Shoe Carnival
$10 Off*
$84.98
$109.99
Men's Nunn Bush Otto Plain Toe Chukka Boot In Brown Size 10
Shoe Carnival
$10 Off*
22% off
$84.98
$109.99
Men's Nunn Bush Otto Plain Toe Chukka Boot In Brown Size 10
Shoe Carnival
$10 Off*
$109.98
$114.99
Men's Florsheim Forge Plain Toe Chukka Dress Boot In Black Size 7
Shoe Carnival
$10 Off*
$109.98
$114.99
Men's Florsheim Forge Plain Toe Chukka Dress Boot In Black Size 7
Shoe Carnival
$10 Off*
$114.98
$149.99
Men's Vintage Foundry Co Milton Chukka Dress Boot In Brown Size 10
Shoe Carnival
$10 Off*
23% off
$114.98
$149.99
Men's Vintage Foundry Co Milton Chukka Dress Boot In Brown Size 10
Shoe Carnival
$10 Off*
$89.98
$109.99
Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 8.5 Wide
Shoe Carnival
$10 Off*
18% off
$89.98
$109.99
Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 8.5 Wide
Shoe Carnival
$10 Off*
$84.98
$109.99
Men's Reserved Footwear Deegan Chukka Dress Boot In Black Size 13
Shoe Carnival
$10 Off*
22% off
$84.98
$109.99
Men's Reserved Footwear Deegan Chukka Dress Boot In Black Size 13
Shoe Carnival
$10 Off*
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Dark Grey Size 11
Shoe Carnival
$10 Off*
21% off
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Dark Grey Size 11
Shoe Carnival
$10 Off*
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Brown Size 10.5
Shoe Carnival
$10 Off*
21% off
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Brown Size 10.5
Shoe Carnival
$10 Off*
$64.98
$114.99
Men's Dr. Scholls Maplewood Chukka Boot In Black Size 14
Shoe Carnival
$10 Off*
43% off
$64.98
$114.99
Men's Dr. Scholls Maplewood Chukka Boot In Black Size 14
Shoe Carnival
$10 Off*
$129.00
$249.00
Rothy's - Men's Chukka Boot In Brown/Neutral, Size 12
Rothy's.com
48% off
$129.00
$249.00
Rothy's - Men's Chukka Boot In Brown/Neutral, Size 12
Rothy's.com
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 15
Rothy's.com
40% off
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 15
Rothy's.com
$179.95
$180.00
Vionic Danfield - Men's Casual Comfort Chukka Boot Tan - 7.5 Medium
Orthotic Shop
$179.95
$180.00
Vionic Danfield - Men's Casual Comfort Chukka Boot Tan - 7.5 Medium
Orthotic Shop
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot - 37640, 10.5 / Medium / Brown
Overlook Boots
4
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot - 37640, 10.5 / Medium / Brown
Overlook Boots
4
$25.49
$59.99
Sonoma Goods For Life® Westynn Men's Chukka Boots, Size: 11
Kohl's
57% off
$25.49
$59.99
Sonoma Goods For Life® Westynn Men's Chukka Boots, Size: 11
Kohl's
$398.00
J.Mclaughlin Men's Baltis Suede Chukka Boot Cognac, Size 9
J.McLaughlin
1
$398.00
J.Mclaughlin Men's Baltis Suede Chukka Boot Cognac, Size 9
J.McLaughlin
1
$295.00
Men's Martin Dingman Blue Ridge Chukkas - Chestnut, Chestnut, 11.5
Patrick James
$295.00
Men's Martin Dingman Blue Ridge Chukkas - Chestnut, Chestnut, 11.5
Patrick James
$69.90
Australian Shearling Chukka Bootie In Tan, Size 6 By Quince
Quince
$69.90
Australian Shearling Chukka Bootie In Tan, Size 6 By Quince
Quince
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 10.5 / Medium / Brown
Overlook Boots
2
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 10.5 / Medium / Brown
Overlook Boots
2
$95.00
Propet Mens Findley Chukka Boot Black 10.5 XX-Wide
Amazon.com
216
Free shipping
$95.00
Propet Mens Findley Chukka Boot Black 10.5 XX-Wide
Amazon.com
216
$41.24
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam | Valentine's Day
JCPenney
In store
32
Curbside
$41.24
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam | Valentine's Day
JCPenney
32
$25.49
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 10.5, Red
Kohl's
247
57% off
$25.49
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 10.5, Red
Kohl's
247
$169.95
Danner Men's Forest Moc 5" Chukka Lifestyle Boot - Chestnut - 37682, 10.5 / Medium / Brown
Overlook Boots
$169.95
Danner Men's Forest Moc 5" Chukka Lifestyle Boot - Chestnut - 37682, 10.5 / Medium / Brown
Overlook Boots
$33.74
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 8 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
62% off
$33.74
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 8 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$110.00
Clarks Mens Eastridge Flat Heel Lace Up Boots | Brown | Regular 7 | Boots Lace Up Boots | Comfort
JCPenney
Free shipping
$110.00
Clarks Mens Eastridge Flat Heel Lace Up Boots | Brown | Regular 7 | Boots Lace Up Boots | Comfort
JCPenney
Free shipping
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    Shop Fashion Chukka Boots for Men

    Sponsored
    $69.98
    $79.99
    Men's Freeman Brent Chukka Boot In Tan Size 8.5
    Shoe Carnival
    $10 Off*
    12% off
    $69.98
    $79.99
    Men's Freeman Brent Chukka Boot In Tan Size 8.5
    Shoe Carnival
    $10 Off*
    $54.98
    $89.99
    Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 11.5
    Shoe Carnival
    $10 Off*
    38% off
    $54.98
    $89.99
    Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 11.5
    Shoe Carnival
    $10 Off*
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Brown Size 13
    Shoe Carnival
    $10 Off*
    25% off
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Brown Size 13
    Shoe Carnival
    $10 Off*
    $34.98
    $44.99
    Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 8
    Shoe Carnival
    $10 Off*
    22% off
    $34.98
    $44.99
    Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 8
    Shoe Carnival
    $10 Off*
    $34.98
    $44.99
    Men's Reserved Footwear Petrus Chukka Dress Boot In Black Size 8
    Shoe Carnival
    $10 Off*
    22% off
    $34.98
    $44.99
    Men's Reserved Footwear Petrus Chukka Dress Boot In Black Size 8
    Shoe Carnival
    $10 Off*
    $74.98
    $99.99
    Men's Reserved Footwear Palmetto Chukka Dress Boot In Brown Size 10.5
    Shoe Carnival
    $10 Off*
    25% off
    $74.98
    $99.99
    Men's Reserved Footwear Palmetto Chukka Dress Boot In Brown Size 10.5
    Shoe Carnival
    $10 Off*
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Dark Tan Size 8.5
    Shoe Carnival
    $10 Off*
    25% off
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Dark Tan Size 8.5
    Shoe Carnival
    $10 Off*
    $74.98
    $94.99
    Men's Dockers Calgary Chukka Boot Oxfords In Taupe Size 12
    Shoe Carnival
    $10 Off*
    21% off
    $74.98
    $94.99
    Men's Dockers Calgary Chukka Boot Oxfords In Taupe Size 12
    Shoe Carnival
    $10 Off*
    $49.98
    $59.99
    Men's New York And Company Kevin Chukka Dress Boot In Cognac Size 9
    Shoe Carnival
    $10 Off*
    16% off
    $49.98
    $59.99
    Men's New York And Company Kevin Chukka Dress Boot In Cognac Size 9
    Shoe Carnival
    $10 Off*
    $89.98
    $119.99
    Men's Vintage Foundry Co Lewis Dress Chukka Boot In Brown Size 8
    Shoe Carnival
    $10 Off*
    25% off
    $89.98
    $119.99
    Men's Vintage Foundry Co Lewis Dress Chukka Boot In Brown Size 8
    Shoe Carnival
    $10 Off*
    $119.98
    $124.99
    Men's Stacy Adams Maxwell Chukka Boot In Cognac Size 11
    Shoe Carnival
    $10 Off*
    $119.98
    $124.99
    Men's Stacy Adams Maxwell Chukka Boot In Cognac Size 11
    Shoe Carnival
    $10 Off*
    $119.98
    $129.99
    Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5
    Shoe Carnival
    $10 Off*
    $119.98
    $129.99
    Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5
    Shoe Carnival
    $10 Off*
    $109.98
    $114.99
    Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 13
    Shoe Carnival
    $10 Off*
    $109.98
    $114.99
    Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 13
    Shoe Carnival
    $10 Off*
    $84.98
    $109.99
    Men's Nunn Bush Otto Plain Toe Chukka Boot In Brown Size 10
    Shoe Carnival
    $10 Off*
    22% off
    $84.98
    $109.99
    Men's Nunn Bush Otto Plain Toe Chukka Boot In Brown Size 10
    Shoe Carnival
    $10 Off*
    $109.98
    $114.99
    Men's Florsheim Forge Plain Toe Chukka Dress Boot In Black Size 7
    Shoe Carnival
    $10 Off*
    $109.98
    $114.99
    Men's Florsheim Forge Plain Toe Chukka Dress Boot In Black Size 7
    Shoe Carnival
    $10 Off*
    $114.98
    $149.99
    Men's Vintage Foundry Co Milton Chukka Dress Boot In Brown Size 10
    Shoe Carnival
    $10 Off*
    23% off
    $114.98
    $149.99
    Men's Vintage Foundry Co Milton Chukka Dress Boot In Brown Size 10
    Shoe Carnival
    $10 Off*
    $89.98
    $109.99
    Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 8.5 Wide
    Shoe Carnival
    $10 Off*
    18% off
    $89.98
    $109.99
    Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 8.5 Wide
    Shoe Carnival
    $10 Off*
    $84.98
    $109.99
    Men's Reserved Footwear Deegan Chukka Dress Boot In Black Size 13
    Shoe Carnival
    $10 Off*
    22% off
    $84.98
    $109.99
    Men's Reserved Footwear Deegan Chukka Dress Boot In Black Size 13
    Shoe Carnival
    $10 Off*