Shop chukka boots for men

Sponsored
$139.99
$160.00
Mens Leather Chukka Boots, Orthopedic Slip On Shoes, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Boots, Verno, 8.5 / Extra Wide / Brown
Orthofeet
12% off
$139.99
$160.00
Mens Leather Chukka Boots, Orthopedic Slip On Shoes, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Boots, Verno, 8.5 / Extra Wide / Brown
Orthofeet
$119.96
$149.95
Men's Founder's Chukka Boots - Brown 013,Shoewidth-M - Duluth Trading Company
Duluth Trading Company
19% off
$119.96
$149.95
Men's Founder's Chukka Boots - Brown 013,Shoewidth-M - Duluth Trading Company
Duluth Trading Company
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot - 37640, 11 / Medium / Brown
Overlook Boots
4
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot - 37640, 11 / Medium / Brown
Overlook Boots
$25.49
$59.99
Sonoma Goods For Life® Westynn Men's Chukka Boots, Size: 13
Kohl's
57% off
$25.49
$59.99
Sonoma Goods For Life® Westynn Men's Chukka Boots, Size: 13
Kohl's
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 11 / Medium / Brown
Overlook Boots
4
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 11 / Medium / Brown
Overlook Boots
$25.49
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 7, Red
Kohl's
57% off
$25.49
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 7, Red
Kohl's
$62.98
Clarks Bushacre 3 Chukka Boot | Men's | Coffee Brown | Size 8.5 | Boots
DSW
12K+
$62.98
Clarks Bushacre 3 Chukka Boot | Men's | Coffee Brown | Size 8.5 | Boots
DSW
$89.99
Clarks Shacre Chukka Boot | Men's | Dark Brown | Size 10 | Boots
DSW
3K+
Free shipping
$89.99
Clarks Shacre Chukka Boot | Men's | Dark Brown | Size 10 | Boots
DSW
$62.98
Clarks Bushacre Chukka Boot | Men's | Sand Suede | Size 8 | Boots
DSW
$62.98
Clarks Bushacre Chukka Boot | Men's | Sand Suede | Size 8 | Boots
DSW
$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
$99.99
$159.99
NORU Hakken ADV Waterproof CE Boots, Black, Mens US 7-12.5/EU 40-47-Dirtbike Boot
Motosport
Free shipping
37% off
$99.99
$159.99
NORU Hakken ADV Waterproof CE Boots, Black, Mens US 7-12.5/EU 40-47-Dirtbike Boot
Motosport
$139.99
$160.00
Most Comfortable Walking Hiking Boots, Customized Arch Support, Waterproof, Men's Hiking Boots | Orthofeet Boots, Ridgewood, 14 / Extra Wide / Brown
Orthofeet
12% off
$139.99
$160.00
Most Comfortable Walking Hiking Boots, Customized Arch Support, Waterproof, Men's Hiking Boots | Orthofeet Boots, Ridgewood, 14 / Extra Wide / Brown
Orthofeet
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 8
Rothy's.com
40% off
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 8
Rothy's.com
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 11
Thursday Boot Company
753
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 11
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Safari Suede Size 16
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Safari Suede Size 16
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 11.5
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 11.5
Thursday Boot Company
$67.50
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
33
25% off
$67.50
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$140.00
Rockport - Men's Classic Break Chukka Boot - 11 m
Rockport US
1K+
$140.00
Rockport - Men's Classic Break Chukka Boot - 11 m
Rockport US
$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
$111.99
$160.00
UGG® Men's Burleigh Chukka Suede Shoes In Chestnut, Size 10.5
Ugg
15
30% off
$111.99
$160.00
UGG® Men's Burleigh Chukka Suede Shoes In Chestnut, Size 10.5
Ugg
$94.99
Timberland Men's Davis Square Chukka Boots | Wheat | Size 10.5 | Nubuck
Shoe Station Feed
$94.99
Timberland Men's Davis Square Chukka Boots | Wheat | Size 10.5 | Nubuck
Shoe Station Feed
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 7 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
70% off
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 7 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 11 | Boots Chukka Boots | Memory Foam
JCPenney
70% off
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 11 | Boots Chukka Boots | Memory Foam
JCPenney
$89.98
$99.99
Timberland Men's Westmore Chukka Boots (Tortoise Brown) - Size 8.0 m
Famous Footwear
Free shipping
10% off
$89.98
$99.99
Timberland Men's Westmore Chukka Boots (Tortoise Brown) - Size 8.0 m
Famous Footwear
$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
$124.99
$150.00
Seniors Support Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Comfortable Shoes, Hunter, 11.5 / Medium / Brown
Orthofeet
411
16% off
$124.99
$150.00
Seniors Support Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Comfortable Shoes, Hunter, 11.5 / Medium / Brown
Orthofeet
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
$159.00
L.L.Bean | Men's Allagash Handsewn Chukka Boots Canyon 7.5 M(D), Suede Leather
L.L.Bean
Free shipping
$159.00
L.L.Bean | Men's Allagash Handsewn Chukka Boots Canyon 7.5 M(D), Suede Leather
L.L.Bean
$159.99
RST Roadster 3 CE Waterproof Boots, Brown, Mens US 13-14.5/EU 48-49 Street Boot
Motosport
Free shipping
$159.99
RST Roadster 3 CE Waterproof Boots, Brown, Mens US 13-14.5/EU 48-49 Street Boot
Motosport
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 12.0 | Brown | Leather/Synthetic
Skechers USA
472
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 12.0 | Brown | Leather/Synthetic
Skechers USA
$104.99
$150.00
UGG® Men's Neumel Distressed Suede Classic Boots In Burnt Cedar, Size 8
Ugg
30% off
$104.99
$150.00
UGG® Men's Neumel Distressed Suede Classic Boots In Burnt Cedar, Size 8
Ugg
$45.00
Men's Jerad Chukka Boots - Goodfellow & Co Brown 10.5
Target
Free shipping
$45.00
Men's Jerad Chukka Boots - Goodfellow & Co Brown 10.5
Target
$39.99
Magellan Outdoors Men's Chukka Boot Brown, 11.5 - Mens Casual At Academy Sports
Academy Sports + Outdoors
$39.99
Magellan Outdoors Men's Chukka Boot Brown, 11.5 - Mens Casual At Academy Sports
Academy Sports + Outdoors
$51.00
$60.00
Deer Stags Bangor Men's Chukka Boots, Size: 10.5, Redwood
Kohl's
46
Free shipping
15% off
$51.00
$60.00
Deer Stags Bangor Men's Chukka Boots, Size: 10.5, Redwood
Kohl's
$140.00
UGG® Men's Neumel Leather Shoes Chukka Boots In Black/, Size 11
Ugg
16K+
$140.00
UGG® Men's Neumel Leather Shoes Chukka Boots In Black/, Size 11
Ugg
$62.99
$89.99
Vance Co. Men's Orson Chukka Boots (Tan) - Size 11.5 m
Famous Footwear
30% off
$62.99
$89.99
Vance Co. Men's Orson Chukka Boots (Tan) - Size 11.5 m
Famous Footwear
Ellis Chukka Boots - Men's
Ellis Chukka Boots - Men's
Feb 4, 2020
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Nov 12, 2017
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esquire.com
How to wear chukka boots: Style tips every man should know
How to wear chukka boots: Style tips every man should know
Oct 21, 2021
themanual.com
The 20 Best Men's Chukka Boots For Real Shoe Enthusiasts
Dec 8, 2020
misiuacademy.com
Bates Lites Buckle Chukka Boot
Jan 10, 2016
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Laval Chukka Boots - Pull-Up - Men's
Sep 6, 2019
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Laval Chukka Boots - Men's
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Nov 26, 2013
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5:16
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19.5K viewsFeb 21, 2019
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ASTON bare-brown chukka boots.
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0:51
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0:15
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0:23
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Jun 5, 2023
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Shop chukka boots for men

Sponsored
$139.99
$160.00
Most Comfortable Walking Hiking Boots, Customized Arch Support, Waterproof, Men's Hiking Boots | Orthofeet Boots, Ridgewood, 14 / Extra Wide / Brown
Orthofeet
12% off
$139.99
$160.00
Most Comfortable Walking Hiking Boots, Customized Arch Support, Waterproof, Men's Hiking Boots | Orthofeet Boots, Ridgewood, 14 / Extra Wide / Brown
Orthofeet
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 8
Rothy's.com
40% off
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 8
Rothy's.com
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 11
Thursday Boot Company
753
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 11
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Safari Suede Size 16
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Safari Suede Size 16
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 11.5
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 11.5
Thursday Boot Company
$67.50
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
33
25% off
$67.50
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$140.00
Rockport - Men's Classic Break Chukka Boot - 11 m
Rockport US
1K+
$140.00
Rockport - Men's Classic Break Chukka Boot - 11 m
Rockport US
$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
$111.99
$160.00
UGG® Men's Burleigh Chukka Suede Shoes In Chestnut, Size 10.5
Ugg
15
30% off
$111.99
$160.00
UGG® Men's Burleigh Chukka Suede Shoes In Chestnut, Size 10.5
Ugg
$94.99
Timberland Men's Davis Square Chukka Boots | Wheat | Size 10.5 | Nubuck
Shoe Station Feed
$94.99
Timberland Men's Davis Square Chukka Boots | Wheat | Size 10.5 | Nubuck
Shoe Station Feed
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 7 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
70% off
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 7 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 11 | Boots Chukka Boots | Memory Foam
JCPenney
70% off
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 11 | Boots Chukka Boots | Memory Foam
JCPenney
$89.98
$99.99
Timberland Men's Westmore Chukka Boots (Tortoise Brown) - Size 8.0 m
Famous Footwear
Free shipping
10% off
$89.98
$99.99
Timberland Men's Westmore Chukka Boots (Tortoise Brown) - Size 8.0 m
Famous Footwear
$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
$124.99
$150.00
Seniors Support Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Comfortable Shoes, Hunter, 11.5 / Medium / Brown
Orthofeet
411
16% off
$124.99
$150.00
Seniors Support Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Comfortable Shoes, Hunter, 11.5 / Medium / Brown
Orthofeet
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
$159.00
L.L.Bean | Men's Allagash Handsewn Chukka Boots Canyon 7.5 M(D), Suede Leather
L.L.Bean
Free shipping
$159.00
L.L.Bean | Men's Allagash Handsewn Chukka Boots Canyon 7.5 M(D), Suede Leather
L.L.Bean
$159.99
RST Roadster 3 CE Waterproof Boots, Brown, Mens US 13-14.5/EU 48-49 Street Boot
Motosport
Free shipping
$159.99
RST Roadster 3 CE Waterproof Boots, Brown, Mens US 13-14.5/EU 48-49 Street Boot
Motosport

Shop chukka boots for men

Sponsored
$139.99
$160.00
Mens Leather Chukka Boots, Orthopedic Slip On Shoes, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Boots, Verno, 8.5 / Extra Wide / Brown
Orthofeet
12% off
$139.99
$160.00
Mens Leather Chukka Boots, Orthopedic Slip On Shoes, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Boots, Verno, 8.5 / Extra Wide / Brown
Orthofeet
$119.96
$149.95
Men's Founder's Chukka Boots - Brown 013,Shoewidth-M - Duluth Trading Company
Duluth Trading Company
19% off
$119.96
$149.95
Men's Founder's Chukka Boots - Brown 013,Shoewidth-M - Duluth Trading Company
Duluth Trading Company
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot - 37640, 11 / Medium / Brown
Overlook Boots
4
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot - 37640, 11 / Medium / Brown
Overlook Boots
$25.49
$59.99
Sonoma Goods For Life® Westynn Men's Chukka Boots, Size: 13
Kohl's
57% off
$25.49
$59.99
Sonoma Goods For Life® Westynn Men's Chukka Boots, Size: 13
Kohl's
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 11 / Medium / Brown
Overlook Boots
4
$159.95
Danner Men's Forest Chukka 4.5" Leather Lifestyle Boot- Bracken- 37641, 11 / Medium / Brown
Overlook Boots
$25.49
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 7, Red
Kohl's
57% off
$25.49
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 7, Red
Kohl's
$62.98
Clarks Bushacre 3 Chukka Boot | Men's | Coffee Brown | Size 8.5 | Boots
DSW
12K+
$62.98
Clarks Bushacre 3 Chukka Boot | Men's | Coffee Brown | Size 8.5 | Boots
DSW
$89.99
Clarks Shacre Chukka Boot | Men's | Dark Brown | Size 10 | Boots
DSW
3K+
Free shipping
$89.99
Clarks Shacre Chukka Boot | Men's | Dark Brown | Size 10 | Boots
DSW
$62.98
Clarks Bushacre Chukka Boot | Men's | Sand Suede | Size 8 | Boots
DSW
$62.98
Clarks Bushacre Chukka Boot | Men's | Sand Suede | Size 8 | Boots
DSW
$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
$99.99
$159.99
NORU Hakken ADV Waterproof CE Boots, Black, Mens US 7-12.5/EU 40-47-Dirtbike Boot
Motosport
Free shipping
37% off
$99.99
$159.99
NORU Hakken ADV Waterproof CE Boots, Black, Mens US 7-12.5/EU 40-47-Dirtbike Boot
Motosport
$139.99
$160.00
Most Comfortable Walking Hiking Boots, Customized Arch Support, Waterproof, Men's Hiking Boots | Orthofeet Boots, Ridgewood, 14 / Extra Wide / Brown
Orthofeet
12% off
$139.99
$160.00
Most Comfortable Walking Hiking Boots, Customized Arch Support, Waterproof, Men's Hiking Boots | Orthofeet Boots, Ridgewood, 14 / Extra Wide / Brown
Orthofeet
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 8
Rothy's.com
40% off
$149.00
$249.00
Rothy's - Men's Chukka Boot In Black/Neutral, Size 8
Rothy's.com
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 11
Thursday Boot Company
753
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Cognac Brown Suede Size 11
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Safari Suede Size 16
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Safari Suede Size 16
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 11.5
Thursday Boot Company
$160.00
Thursday Boot Company Men's Suede Chukka Scout Chukka Boot In Mocha Brown Suede Size 11.5
Thursday Boot Company
$67.50
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
33
25% off
$67.50
$90.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$140.00
Rockport - Men's Classic Break Chukka Boot - 11 m
Rockport US
1K+
$140.00
Rockport - Men's Classic Break Chukka Boot - 11 m
Rockport US

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

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