Shop The Best Casual Shoes or Chukka Boots for Men

Sponsored
About our ads
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$139.99
Carhartt Men's Wedge Plain Toe Chukka | Dark Brown | 8.5 W
Carhartt
4
$139.99
Carhartt Men's Wedge Plain Toe Chukka | Dark Brown | 8.5 W
Carhartt
4
$70.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$70.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$89.99
Skechers USA Men's Resment Korver Chukka Boot
Amazon.com
3K+
Free shipping
$89.99
Skechers USA Men's Resment Korver Chukka Boot
Amazon.com
3K+
$1,250.00
Brunello Cucinelli, Suede Chukka Boots, Brown, 40
Brunello Cucinelli Online Boutique
Free shipping
$1,250.00
Brunello Cucinelli, Suede Chukka Boots, Brown, 40
Brunello Cucinelli Online Boutique
Free shipping
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 10
Shoes for Crews
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 10
Shoes for Crews
$88.38
$119.99
ROPER Mens Clearcut Chukka Casual Boots Ankle - Brown Tan 13
Amazon.com
303
Free shipping
26% off
$88.38
$119.99
ROPER Mens Clearcut Chukka Casual Boots Ankle - Brown Tan 13
Amazon.com
303
$169.00
Most Comfortable Leather Boots For Men With Arch Support & Heel Pain Relief | Chukka Style, Lightweight, Work & Travel | KURU DRAFT Aalto Dark Brown
KURU
$169.00
Most Comfortable Leather Boots For Men With Arch Support & Heel Pain Relief | Chukka Style, Lightweight, Work & Travel | KURU DRAFT Aalto Dark Brown
KURU
$99.99
Carhartt Haslett Canvas Men's Chukka Boots - Moc Toe Work Boots For Men With Lightweight LWD Midsole, Arch Support Footbed And Fastdry Lining
Amazon.com
4
Free shipping
$99.99
Carhartt Haslett Canvas Men's Chukka Boots - Moc Toe Work Boots For Men With Lightweight LWD Midsole, Arch Support Footbed And Fastdry Lining
Amazon.com
4
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Dark Beige, 11
Sperry
61% off
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Dark Beige, 11
Sperry
$65.99
$109.99
Vance Stratton Men's Casual Chukka Boots, Size: 10.5, Brown
Kohl's
Free shipping
40% off
$65.99
$109.99
Vance Stratton Men's Casual Chukka Boots, Size: 10.5, Brown
Kohl's
Free shipping
$129.99
Carhartt Men's Lightweight Wedge Moc Toe Chukka | Sable | 11 m
Carhartt
4K+
$129.99
Carhartt Men's Lightweight Wedge Moc Toe Chukka | Sable | 11 m
Carhartt
4K+
$72.49
Vance Mens Stratton Medium And Wide Width Plain Toe Casual Chukka Boot - Walnut - 13
Overstock.com
4
$72.49
Vance Mens Stratton Medium And Wide Width Plain Toe Casual Chukka Boot - Walnut - 13
Overstock.com
4
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Brown, 10
Sperry
61% off
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Brown, 10
Sperry
$525.00
Allen Edmonds Chandler Weatherproof Chukka Boot Boots In Pecan Leather, Size 9.5 D
Allen Edmonds
$525.00
Allen Edmonds Chandler Weatherproof Chukka Boot Boots In Pecan Leather, Size 9.5 D
Allen Edmonds
$109.99
Carhartt Men's Detroit Chukka | Dark Brown | 10 m
Carhartt
2
$109.99
Carhartt Men's Detroit Chukka | Dark Brown | 10 m
Carhartt
2
$925.00
Tod's Men's Suede Desert Boots, Brown, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$925.00
Tod's Men's Suede Desert Boots, Brown, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$199.99
$449.00
Brooks Brothers Men's Chukka Boots | Brown | Size 10 D | Shop Holiday Gifts And Sets
Brooks Brothers
4
55% off
$199.99
$449.00
Brooks Brothers Men's Chukka Boots | Brown | Size 10 D | Shop Holiday Gifts And Sets
Brooks Brothers
4
$169.95
Men's Founder's Chukka Boots - Brown 008,Shoewidth-M - Duluth Trading Company
Duluth Trading Company
$169.95
Men's Founder's Chukka Boots - Brown 008,Shoewidth-M - Duluth Trading Company
Duluth Trading Company
$100.00
Sperry Top-Sider Newman Chukka Boot In Brown, 10.5
Sperry
$100.00
Sperry Top-Sider Newman Chukka Boot In Brown, 10.5
Sperry
$55.97
$100.00
Men's Caterpillar Threshold Chukka Rugged Casual Boots, Size: 11, Bungee Cord
Kohl's
23
Free shipping
44% off
$55.97
$100.00
Men's Caterpillar Threshold Chukka Rugged Casual Boots, Size: 11, Bungee Cord
Kohl's
23
$89.99
$159.95
Rockport Classic Break Chukka Men's Boots Dark Brown Leather : 8.5 W (EE)
Zappos
2K+
43% off
$89.99
$159.95
Rockport Classic Break Chukka Men's Boots Dark Brown Leather : 8.5 W (EE)
Zappos
2K+
$108.00
$180.00
Men's Suede Chukka Lace Up Boot Tan/Natural Regular Size 10
Banana Republic Factory
40% off
$108.00
$180.00
Men's Suede Chukka Lace Up Boot Tan/Natural Regular Size 10
Banana Republic Factory
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 7.5 | Boots | Chukka
DSW
7
Free shipping
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 7.5 | Boots | Chukka
DSW
7
$525.00
Allen Edmonds Chandler Chukka Boot Boots In Tan Nubuck, Size 8.5 D
Allen Edmonds
$525.00
Allen Edmonds Chandler Chukka Boot Boots In Tan Nubuck, Size 8.5 D
Allen Edmonds
$72.49
Vance Mens Stratton Medium And Wide Width Plain Toe Casual Chukka Boot - Black - 10
Overstock.com
$72.49
Vance Mens Stratton Medium And Wide Width Plain Toe Casual Chukka Boot - Black - 10
Overstock.com
$69.99
$94.99
Dockers Men's Davis Rugged Casual Chukka Boots (Dark Brown) - Size 7.0 m
Famous Footwear
26% off
$69.99
$94.99
Dockers Men's Davis Rugged Casual Chukka Boots (Dark Brown) - Size 7.0 m
Famous Footwear
$101.97
$169.95
Men's Nubuck Chukka Lace Up Boots - Lands' End - Brown - 10
Lands' End
39% off
$101.97
$169.95
Men's Nubuck Chukka Lace Up Boots - Lands' End - Brown - 10
Lands' End
$119.99
Rockport Wide Width Classic Break Chukka Boot | Men's | Brown | Size 10 | Boots | Chukka | Lace-Up
DSW
2K+
Free shipping
$119.99
Rockport Wide Width Classic Break Chukka Boot | Men's | Brown | Size 10 | Boots | Chukka | Lace-Up
DSW
2K+
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 8 | Boots Chukka Boots | Memory Foam
JCPenney
70% off
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 8 | Boots Chukka Boots | Memory Foam
JCPenney
$158.95
Johnston & Murphy Braxton Chukka Men's Boots Brown Oiled Full Grain : 10.5 m (D), Leather
Zappos
$158.95
Johnston & Murphy Braxton Chukka Men's Boots Brown Oiled Full Grain : 10.5 m (D), Leather
Zappos
$975.00
Tod's Men's Winter Gommino Suede Desert Boots, Brown, Men's, 9D, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$975.00
Tod's Men's Winter Gommino Suede Desert Boots, Brown, Men's, 9D, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$525.00
Allen Edmonds Chandler Weatherproof Chukka Boot Boots In Teak Leather, Size 10.0 D
Allen Edmonds
$525.00
Allen Edmonds Chandler Weatherproof Chukka Boot Boots In Teak Leather, Size 10.0 D
Allen Edmonds
$41.99
$100.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 8 1/2 | Boots Chukka Boots | Memory Foam | Fall Fashion | Holiday Gifts
JCPenney
35
58% off
$41.99
$100.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 8 1/2 | Boots Chukka Boots | Memory Foam | Fall Fashion | Holiday Gifts
JCPenney
35
$69.99
$110.00
Clarks Mens Shepton Flat Heel Chukka Boots | Beige | Regular 10 | Boots Chukka Boots | Comfort
JCPenney
1
Free shipping
36% off
$69.99
$110.00
Clarks Mens Shepton Flat Heel Chukka Boots | Beige | Regular 10 | Boots Chukka Boots | Comfort
JCPenney
1
$169.00
Best Mena€™S Chukka Boot For Heel Pain Relief, Plantar Fasciitis, Stylish Work & Everyday Wear - Size 7-13 | Brown Leather DRAFT Aalto KURU
KURU
$169.00
Best Mena€™S Chukka Boot For Heel Pain Relief, Plantar Fasciitis, Stylish Work & Everyday Wear - Size 7-13 | Brown Leather DRAFT Aalto KURU
KURU
Sponsored
Top 10 Best Chukka Shoes For Men of 2025
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Shop The Best Casual Shoes or Chukka Boots for Men

Sponsored
About our ads
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$139.99
Carhartt Men's Wedge Plain Toe Chukka | Dark Brown | 8.5 W
Carhartt
4
$139.99
Carhartt Men's Wedge Plain Toe Chukka | Dark Brown | 8.5 W
Carhartt
4
$70.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$70.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$89.99
Skechers USA Men's Resment Korver Chukka Boot
Amazon.com
3K+
Free shipping
$89.99
Skechers USA Men's Resment Korver Chukka Boot
Amazon.com
3K+
$1,250.00
Brunello Cucinelli, Suede Chukka Boots, Brown, 40
Brunello Cucinelli Online Boutique
Free shipping
$1,250.00
Brunello Cucinelli, Suede Chukka Boots, Brown, 40
Brunello Cucinelli Online Boutique
Free shipping
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 10
Shoes for Crews
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 10
Shoes for Crews
$88.38
$119.99
ROPER Mens Clearcut Chukka Casual Boots Ankle - Brown Tan 13
Amazon.com
303
Free shipping
26% off
$88.38
$119.99
ROPER Mens Clearcut Chukka Casual Boots Ankle - Brown Tan 13
Amazon.com
303
$169.00
Most Comfortable Leather Boots For Men With Arch Support & Heel Pain Relief | Chukka Style, Lightweight, Work & Travel | KURU DRAFT Aalto Dark Brown
KURU
$169.00
Most Comfortable Leather Boots For Men With Arch Support & Heel Pain Relief | Chukka Style, Lightweight, Work & Travel | KURU DRAFT Aalto Dark Brown
KURU
$99.99
Carhartt Haslett Canvas Men's Chukka Boots - Moc Toe Work Boots For Men With Lightweight LWD Midsole, Arch Support Footbed And Fastdry Lining
Amazon.com
4
Free shipping
$99.99
Carhartt Haslett Canvas Men's Chukka Boots - Moc Toe Work Boots For Men With Lightweight LWD Midsole, Arch Support Footbed And Fastdry Lining
Amazon.com
4
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Dark Beige, 11
Sperry
61% off
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Dark Beige, 11
Sperry
$65.99
$109.99
Vance Stratton Men's Casual Chukka Boots, Size: 10.5, Brown
Kohl's
Free shipping
40% off
$65.99
$109.99
Vance Stratton Men's Casual Chukka Boots, Size: 10.5, Brown
Kohl's
Free shipping
$129.99
Carhartt Men's Lightweight Wedge Moc Toe Chukka | Sable | 11 m
Carhartt
4K+
$129.99
Carhartt Men's Lightweight Wedge Moc Toe Chukka | Sable | 11 m
Carhartt
4K+
$72.49
Vance Mens Stratton Medium And Wide Width Plain Toe Casual Chukka Boot - Walnut - 13
Overstock.com
4
$72.49
Vance Mens Stratton Medium And Wide Width Plain Toe Casual Chukka Boot - Walnut - 13
Overstock.com
4
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Brown, 10
Sperry
61% off
$49.98
$130.00
Sperry Top-Sider Authentic Original™ Chukka Boot In Brown, 10
Sperry
$525.00
Allen Edmonds Chandler Weatherproof Chukka Boot Boots In Pecan Leather, Size 9.5 D
Allen Edmonds
$525.00
Allen Edmonds Chandler Weatherproof Chukka Boot Boots In Pecan Leather, Size 9.5 D
Allen Edmonds
$109.99
Carhartt Men's Detroit Chukka | Dark Brown | 10 m
Carhartt
2
$109.99
Carhartt Men's Detroit Chukka | Dark Brown | 10 m
Carhartt
2
$925.00
Tod's Men's Suede Desert Boots, Brown, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$925.00
Tod's Men's Suede Desert Boots, Brown, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$199.99
$449.00
Brooks Brothers Men's Chukka Boots | Brown | Size 10 D | Shop Holiday Gifts And Sets
Brooks Brothers
4
55% off
$199.99
$449.00
Brooks Brothers Men's Chukka Boots | Brown | Size 10 D | Shop Holiday Gifts And Sets
Brooks Brothers
4