Best Seller
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$102.60

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$160.00

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$102.60

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$74.90

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$144.00

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$144.00

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$144.00

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$160.00

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$84.93

FREE shipping

go to store
Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Kenneth Cole New York Stamp Leather Chukka Boot Dark Brown

Plain toe dress chukka boot with a burnished leather upper more

$59.23

FREE shipping

go to store
Cole Haan Men's Grand Tour Chukka Boot, Chestnut Leather/Ivory 7.5 M US

Cole Haan Men's Grand Tour Chukka Boot, Chestnut Leather/Ivory 7.5 M US

Cole haan grand tour - the fusion of style and engineering for enhanced comfort for your casual to dress needs. more

$48.39

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 115 M US

Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 115 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$68.27

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 080 W US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 080 W US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$69.58

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 105 M US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 105 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$69.34

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 095 M US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 095 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 150 M US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 150 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$97.36

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 130 M US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 130 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$47.97

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 095 W US

Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 095 W US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
CLARKS Men's Grandin Mid Chukka Boot, Dark tan Leather, 130 M US

CLARKS Men's Grandin Mid Chukka Boot, Dark tan Leather, 130 M US

The grand in mid by Clarks collection is a unique fusion between dress boot and sneaker that is sure to impress. Crafted of full grain leather or suede, this lace-up chukka boot features contrast stitching and sits on a durable rubber sole to provide... more

$110.00

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 075 M US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 075 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 115 W US

Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 115 W US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
Bostonian Men's Dezmin Mid Chukka Boot, Black Leather, 12 M US

Bostonian Men's Dezmin Mid Chukka Boot, Black Leather, 12 M US

The dezmin mid by Bostonian commonwealth is a modern, dress casual boot that is equally versatile as it is comfortable. Its classic chukka boot silhouette is crafted in rich leather or suede and boasts a flexible, contrasting outsole. Inside, a... more

$69.97

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 085 M US

Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 085 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,10.5 M US

Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,10.5 M US

Clarks has been in business for over 100 years making very fine men's dress shoes in a variety of styles. Featuring a wide range of top-quality components, Clarks gives you the options you desire in the quality you demand. more

$54.99

go to store
Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,14 M US

Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,14 M US

Clarks has been in business for over 100 years making very fine men's dress shoes in a variety of styles. Featuring a wide range of top-quality components, Clarks gives you the options you desire in the quality you demand. more

$89.99

FREE shipping

go to store
Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,13 M US

Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,13 M US

Clarks has been in business for over 100 years making very fine men's dress shoes in a variety of styles. Featuring a wide range of top-quality components, Clarks gives you the options you desire in the quality you demand. more

$59.31

go to store
Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,8 M US

Clarks Men's Stinson Hi Chukka Boot,Brown Oily Leather,8 M US

Clarks has been in business for over 100 years making very fine men's dress shoes in a variety of styles. Featuring a wide range of top-quality components, Clarks gives you the options you desire in the quality you demand. more

$59.99

go to store
Clarks Men's Stinson Hi Chukka Boot,Black Leather,12 M US

Clarks Men's Stinson Hi Chukka Boot,Black Leather,12 M US

Clarks has been in business for over 100 years making very fine men's dress shoes in a variety of styles. Featuring a wide range of top-quality components, Clarks gives you the options you desire in the quality you demand. more

$74.95

FREE shipping

go to store
Bostonian Men's Maxton Mid Chukka Boot, Dark tan Leather, 070 M US

Bostonian Men's Maxton Mid Chukka Boot, Dark tan Leather, 070 M US

The maxton mid brings the boot trend to a sharp dress silhouette with Bostonian quality. This lace-up style is crafted from full grain leather with cap toe stitching and clean lines. Inside, a removable ortholite footbed provides supreme comfort, while... more

$110.00

FREE shipping

go to store
Bostonian Men's Maxton Mid Chukka Boot, Dark Brown Leather, 085 M US

Bostonian Men's Maxton Mid Chukka Boot, Dark Brown Leather, 085 M US

The maxton mid brings the boot trend to a sharp dress silhouette with Bostonian quality. This lace-up style is crafted from full grain leather with cap toe stitching and clean lines. Inside, a removable ortholite footbed provides supreme comfort, while... more

$110.00

FREE shipping

go to store
Bostonian Men's Maxton Mid Chukka Boot Black Leather 100 M US

Bostonian Men's Maxton Mid Chukka Boot Black Leather 100 M US

The maxton mid brings the boot trend to a sharp dress silhouette with Bostonian quality. This lace-up style is crafted from full grain leather with cap toe stitching and clean lines. Inside, a removable ortholite footbed provides supreme comfort, while... more

$99.99

FREE shipping

go to store
Bostonian Men's Maxton Mid Chukka Boot, Black Leather, 075 M US

Bostonian Men's Maxton Mid Chukka Boot, Black Leather, 075 M US

The maxton mid brings the boot trend to a sharp dress silhouette with Bostonian quality. This lace-up style is crafted from full grain leather with cap toe stitching and clean lines. Inside, a removable ortholite footbed provides supreme comfort, while... more

$110.00

FREE shipping

go to store
Bostonian Men's Dezmin Mid Chukka Boot Dark Brown Leather 075 M US

Bostonian Men's Dezmin Mid Chukka Boot Dark Brown Leather 075 M US

This low boot has a sleek, sharp profile that compliments dress looks and elevates jeans. Its upper is crafted from lush suede, and a full grain leather sockliner keeps feet comfortable. The shoe stays lightweight thanks to its eva outsole, and a... more

$89.99

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 105 W US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 105 W US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 110 M US

Bostonian Men's Birkett Mid Chukka Boot, Black Leather, 110 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
Bostonian Men's Birkett Mid Chukka Boot Black Leather 120 M US

Bostonian Men's Birkett Mid Chukka Boot Black Leather 120 M US

A sophisticated dress boot crafted of premium leather, makes the birkett mid by Bostonian a refined addition to your shoe collection. Smooth textile linings, a lightweight eva sole and removable ortholite footbed join to provide maximum comfort and... more

$100.00

FREE shipping

go to store
CLARKS Men's Grandin Mid Chukka Boot, Dark tan Leather, 080 M US

CLARKS Men's Grandin Mid Chukka Boot, Dark tan Leather, 080 M US

The grand in mid by Clarks collection is a unique fusion between dress boot and sneaker that is sure to impress. Crafted of full grain leather or suede, this lace-up chukka boot features contrast stitching and sits on a durable rubber sole to provide... more

$110.00

FREE shipping

go to store
Bostonian Men's Dezmin Mid Chukka Boot Black Leather 9 M US

Bostonian Men's Dezmin Mid Chukka Boot Black Leather 9 M US

The dezmin mid by Bostonian commonwealth is a modern, dress casual boot that is equally versatile as it is comfortable. Its classic chukka boot silhouette is crafted in rich leather or suede and boasts a flexible, contrasting outsole. Inside, a... more

$120.00

FREE shipping

go to store

More information about Men's Shoes

Best prices on Boots dress leather chukka 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.