Shop Best Men Chukka Boots

Sponsored
$64.98
$89.99
Men's Vance Co. Orson Chukka Boot In Tan Size 13
Shoe Carnival
$10 Off*
27% off
$64.98
$89.99
Men's Vance Co. Orson Chukka Boot In Tan Size 13
Shoe Carnival
$10 Off*
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Brown Size 11
Shoe Carnival
$10 Off*
25% off
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Brown Size 11
Shoe Carnival
$10 Off*
$69.98
$79.99
Men's Freeman Brent Chukka Boot In Tan Size 12
Shoe Carnival
$10 Off*
12% off
$69.98
$79.99
Men's Freeman Brent Chukka Boot In Tan Size 12
Shoe Carnival
$10 Off*
$54.98
$89.99
Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 10.5
Shoe Carnival
$10 Off*
38% off
$54.98
$89.99
Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 10.5
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*
$79.98
$94.99
Men's Nunn Bush Otto Plain Toe Chukka Boot In Navy Size 10
Shoe Carnival
$10 Off*
15% off
$79.98
$94.99
Men's Nunn Bush Otto Plain Toe Chukka Boot In Navy Size 10
Shoe Carnival
$10 Off*
$89.98
$114.99
Men's Nunn Bush Denali Plain Toe Chukka Waterproof Boot In Black Size 9
Shoe Carnival
$10 Off*
21% off
$89.98
$114.99
Men's Nunn Bush Denali Plain Toe Chukka Waterproof Boot In Black Size 9
Shoe Carnival
$10 Off*
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Brown Size 8
Shoe Carnival
$10 Off*
21% off
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Brown Size 8
Shoe Carnival
$10 Off*
$34.98
$44.99
Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 11
Shoe Carnival
$10 Off*
22% off
$34.98
$44.99
Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 11
Shoe Carnival
$10 Off*
$119.98
$129.99
Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5 Wide
Shoe Carnival
$10 Off*
$119.98
$129.99
Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5 Wide
Shoe Carnival
$10 Off*
$89.98
$109.99
Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 10.5 Wide
Shoe Carnival
$10 Off*
18% off
$89.98
$109.99
Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 10.5 Wide
Shoe Carnival
$10 Off*
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Dark Grey Size 10.5
Shoe Carnival
$10 Off*
21% off
$89.98
$114.99
Men's Dr. Scholls Madison Men Chukka Boot In Dark Grey Size 10.5
Shoe Carnival
$10 Off*
$109.98
$114.99
Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 9.5
Shoe Carnival
$10 Off*
$109.98
$114.99
Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 9.5
Shoe Carnival
$10 Off*
$134.98
$139.99
Men's Florsheim Rucci Plain Toe Chukka Dress Boot In Black Size 8 Wide
Shoe Carnival
$10 Off*
$134.98
$139.99
Men's Florsheim Rucci Plain Toe Chukka Dress Boot In Black Size 8 Wide
Shoe Carnival
$10 Off*
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Dark Tan Size 9
Shoe Carnival
$10 Off*
25% off
$59.98
$79.99
Men's Dockers Rowan Chukka Boot In Dark Tan Size 9
Shoe Carnival
$10 Off*
$89.98
$119.99
Men's Cole Haan Grand + Ultra Chukka Dress Shoes In British Tan/Ivo Size 11
Shoe Carnival
$10 Off*
25% off
$89.98
$119.99
Men's Cole Haan Grand + Ultra Chukka Dress Shoes In British Tan/Ivo Size 11
Shoe Carnival
$10 Off*
$74.98
$94.99
Men's Dockers Calgary Chukka Boot Oxfords In Briar Size 7
Shoe Carnival
$10 Off*
21% off
$74.98
$94.99
Men's Dockers Calgary Chukka Boot Oxfords In Briar Size 7
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*
$54.98
$64.99
Men's Reserved Footwear Lloyd Boot In Brown Size 11
Shoe Carnival
$10 Off*
15% off
$54.98
$64.99
Men's Reserved Footwear Lloyd Boot In Brown Size 11
Shoe Carnival
$10 Off*
$200.00
HOKA Men's Transport Chukka GTX Shoes In Asteroid/Stardust, Size 8
HOKA (hoka.com)
Free shipping
$200.00
HOKA Men's Transport Chukka GTX Shoes In Asteroid/Stardust, Size 8
HOKA (hoka.com)
Free shipping
$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
$200.00
HOKA Men's Transport Chukka GTX Shoes In Oak/Alabaster, Size 12.5
HOKA (hoka.com)
Free shipping
$200.00
HOKA Men's Transport Chukka GTX Shoes In Oak/Alabaster, Size 12.5
HOKA (hoka.com)
Free shipping
$200.00
HOKA Men's Transport Chukka GTX Shoes In Farro/Sesame, Size 12
HOKA (hoka.com)
Free shipping
$200.00
HOKA Men's Transport Chukka GTX Shoes In Farro/Sesame, Size 12
HOKA (hoka.com)
Free shipping
$200.00
HOKA Men's Transport Chukka GTX Shoes In Oat Milk/Alabaster, Size 9.5
HOKA (hoka.com)
Free shipping
$200.00
HOKA Men's Transport Chukka GTX Shoes In Oat Milk/Alabaster, Size 9.5
HOKA (hoka.com)
Free shipping
$179.00
L.L.Bean | Men's Portland Boots, Lace-Up Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$179.00
L.L.Bean | Men's Portland Boots, Lace-Up Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$129.00
$249.00
Rothy's - Men's Chukka Boot In Brown/Neutral, Size 10.5
Rothy's.com
48% off
$129.00
$249.00
Rothy's - Men's Chukka Boot In Brown/Neutral, Size 10.5
Rothy's.com
$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
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 11.5 / Medium / Brown
Overlook Boots
4
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 11.5 / Medium / Brown
Overlook Boots
4
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Arizona Adobe Size 8.5
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Arizona Adobe Size 8.5
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 10
Thursday Boot Company
687
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 10
Thursday Boot Company
687
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Tan 'Dune' Suede Size 13
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Tan 'Dune' Suede Size 13
Thursday Boot Company
$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
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 14
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 14
Thursday Boot Company
$160.00
Men's Scout Chukka Boot In Ash Grey Suede Size 9.5 By Thursday Boot Company
Thursday Boot Company
$160.00
Men's Scout Chukka Boot In Ash Grey Suede Size 9.5 By Thursday Boot Company
Thursday Boot Company
$159.00
L.L.Bean | Men's Bean Boots, 6.5" Chelsea Allspice/Bean Boot Brown/Gum 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$159.00
L.L.Bean | Men's Bean Boots, 6.5" Chelsea Allspice/Bean Boot Brown/Gum 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 10.5
Rothy's.com
40% off
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 10.5
Rothy's.com
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    Shop Best Men Chukka Boots

    Sponsored
    $64.98
    $89.99
    Men's Vance Co. Orson Chukka Boot In Tan Size 13
    Shoe Carnival
    $10 Off*
    27% off
    $64.98
    $89.99
    Men's Vance Co. Orson Chukka Boot In Tan Size 13
    Shoe Carnival
    $10 Off*
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Brown Size 11
    Shoe Carnival
    $10 Off*
    25% off
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Brown Size 11
    Shoe Carnival
    $10 Off*
    $69.98
    $79.99
    Men's Freeman Brent Chukka Boot In Tan Size 12
    Shoe Carnival
    $10 Off*
    12% off
    $69.98
    $79.99
    Men's Freeman Brent Chukka Boot In Tan Size 12
    Shoe Carnival
    $10 Off*
    $54.98
    $89.99
    Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 10.5
    Shoe Carnival
    $10 Off*
    38% off
    $54.98
    $89.99
    Men's Deer Stags Bangor Chukka Boot In Redwood/Dark Brown Size 10.5
    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*
    $79.98
    $94.99
    Men's Nunn Bush Otto Plain Toe Chukka Boot In Navy Size 10
    Shoe Carnival
    $10 Off*
    15% off
    $79.98
    $94.99
    Men's Nunn Bush Otto Plain Toe Chukka Boot In Navy Size 10
    Shoe Carnival
    $10 Off*
    $89.98
    $114.99
    Men's Nunn Bush Denali Plain Toe Chukka Waterproof Boot In Black Size 9
    Shoe Carnival
    $10 Off*
    21% off
    $89.98
    $114.99
    Men's Nunn Bush Denali Plain Toe Chukka Waterproof Boot In Black Size 9
    Shoe Carnival
    $10 Off*
    $89.98
    $114.99
    Men's Dr. Scholls Madison Men Chukka Boot In Brown Size 8
    Shoe Carnival
    $10 Off*
    21% off
    $89.98
    $114.99
    Men's Dr. Scholls Madison Men Chukka Boot In Brown Size 8
    Shoe Carnival
    $10 Off*
    $34.98
    $44.99
    Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 11
    Shoe Carnival
    $10 Off*
    22% off
    $34.98
    $44.99
    Men's Reserved Footwear Petrus Chukka Dress Boot In Grey Size 11
    Shoe Carnival
    $10 Off*
    $119.98
    $129.99
    Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5 Wide
    Shoe Carnival
    $10 Off*
    $119.98
    $129.99
    Men's Stacy Adams Martfield Dress Chukka Boot In Sand Size 10.5 Wide
    Shoe Carnival
    $10 Off*
    $89.98
    $109.99
    Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 10.5 Wide
    Shoe Carnival
    $10 Off*
    18% off
    $89.98
    $109.99
    Men's Clarks Bushacre 3 Chukka Boot In Dark Brown Size 10.5 Wide
    Shoe Carnival
    $10 Off*
    $89.98
    $114.99
    Men's Dr. Scholls Madison Men Chukka Boot In Dark Grey Size 10.5
    Shoe Carnival
    $10 Off*
    21% off
    $89.98
    $114.99
    Men's Dr. Scholls Madison Men Chukka Boot In Dark Grey Size 10.5
    Shoe Carnival
    $10 Off*
    $109.98
    $114.99
    Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 9.5
    Shoe Carnival
    $10 Off*
    $109.98
    $114.99
    Men's Florsheim Forge Plain Toe Chukka Dress Boot In Cognac Size 9.5
    Shoe Carnival
    $10 Off*
    $134.98
    $139.99
    Men's Florsheim Rucci Plain Toe Chukka Dress Boot In Black Size 8 Wide
    Shoe Carnival
    $10 Off*
    $134.98
    $139.99
    Men's Florsheim Rucci Plain Toe Chukka Dress Boot In Black Size 8 Wide
    Shoe Carnival
    $10 Off*
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Dark Tan Size 9
    Shoe Carnival
    $10 Off*
    25% off
    $59.98
    $79.99
    Men's Dockers Rowan Chukka Boot In Dark Tan Size 9
    Shoe Carnival
    $10 Off*
    $89.98
    $119.99
    Men's Cole Haan Grand + Ultra Chukka Dress Shoes In British Tan/Ivo Size 11
    Shoe Carnival
    $10 Off*
    25% off
    $89.98
    $119.99
    Men's Cole Haan Grand + Ultra Chukka Dress Shoes In British Tan/Ivo Size 11
    Shoe Carnival
    $10 Off*
    $74.98
    $94.99
    Men's Dockers Calgary Chukka Boot Oxfords In Briar Size 7
    Shoe Carnival
    $10 Off*
    21% off
    $74.98
    $94.99
    Men's Dockers Calgary Chukka Boot Oxfords In Briar Size 7
    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*

    • 10 Best Men's Chukka Boots - Our #1 Pick Will Surprise You

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