Best Seller
Territory Boots Redwoods Chukka Boot - Grey - 9.5

Territory Boots Redwoods Chukka Boot - Grey - 9.5

The Redwoods chukka boot from Territory will be perfect for that easy business casual look. The 6 mm Tru Comfort Foamâ„¢ insole, round toe, and cushioned collar tongue will let you travel anywhere with ease. An EVA outsole, genuine leather, and lace-up... more

$109.99

go to store
J. Crew Shoes | J Crew Mcalister Tan Suede Wedge Bootie | Color: Tan | Size: 7

J. Crew Shoes | J Crew Mcalister Tan Suede Wedge Bootie | Color: Tan | Size: 7

Classic And Timeless Style With A Minimalist Look Ina Neutral Color. J Crew Mcalister Tan Khaki Suede Leather Chukka Style Lace Up Desert Bootie With 2 3/4" Wedge Heel & Rubber Sole. Cushioned Footbed. Leather Sock. Made In Italy Boots Measure 6 1/4"... more

$35.00

go to store
Best Seller
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 10.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 10.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 12

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 12

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 9.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 9.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 8

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 8

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 11.5

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 11.5

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 10

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 10

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 13

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 13

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 13

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 13

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 13

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 13

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 12

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 12

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 8.5

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 8.5

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 10.5

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 10.5

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 9

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 9

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 10

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 10

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 8

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 8

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 11

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 11

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 8.5

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 8.5

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 9.5

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 9.5

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 9

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 9

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 9.5

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 9.5

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 9

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 9

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 10.5

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 10.5

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 8

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 8

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 9.5

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 9.5

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 10.5

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 10.5

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 14

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 14

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 12

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 12

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 10

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 10

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 11.5

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 11.5

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

go to store
Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 12

Vance Co. Shoes Vance Co. Austin Cap Toe Chukka Boot - Grey - 12

A casual but always high-minded look, the Chukka boot. The Austin features premium faux leather uppers cleverly contrasted with embossed accents on either side. A lace-up closure, cap toe, cushioned footbed and durable rubber outsole complete this... more

$64.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 13

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 13

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 11

Thomas and Vine Banks Moc Toe Chukka Boot - Grey - 11

Style comes easy with the Banks chukka boot by Thomas & Vine in your rotation. This genuine leather casual style is detailed with a classic two-eye lace-up closure and a round moc-toe for a modern look. Comfort details like a 12 mm Tru Comfort Foamâ„¢... more

$129.99

go to store
Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 8.5

Vance Co. Shoes Vaughn Lace-Up Chukka Boot - Grey - 8.5

The Vaughn boot by Vance Co. is so simple yet stylish that you'll want to wear it every day. Soft vegan leather uppers and a 6 mm Tru Comfort Foamâ„¢ insole make this chukka boot super comfortable. A three-eye lace-up closure and low block heel add a... more

$79.99

go to store
Georgia Boot Wedge Chukka Soft Toe - Mens 8.5 Gold Boot Medium

Georgia Boot Wedge Chukka Soft Toe - Mens 8.5 Gold Boot Medium

*A rugged, comfortable chukka boot that's built tough for farm and ranch wear *Full grain SPR™ Superior Performing Ranch leather upper is stronger and more abrasion-resistant than regular leather, while resisting barnyard acids and chemicals *Lace-up... more

$149.95

FREE shipping

go to store

More information about Men's Shoes

Best prices on Leather chukka boots, Gray in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.