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Frye Gates Chukka Shoe - Men's Cognac, 10.0

Frye Gates Chukka Shoe - Men's Cognac, 10.0

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Size 10.0, Color Cognac. When you're a sneaker kind of guy, there's nothing more annoying than shopping for work appropriate shoes that waffle somewhere between bourgeois and trying too hard. Well, sneakerheads rejoice--introducing, the Frye Men's... more

$287.95 $143.97

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(125,000+)
Timberland Britton Hill Chukka Shoe - Men's

Timberland Britton Hill Chukka Shoe - Men's

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At a whopping 345 feet above sea level, Britton Hill is the highest point in Florida, so wearing anything more than flip-flops when you "climb" it is probably overkill. That said, Timberland's Britton Hill Men's Chukka Shoe will happily go just about... more

$159.95 $111.96

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(125,000+)
Skechers Resment Chukka Boot Chukka Brown Boot Mens Casual Dress Boots, Men's, Size: 10

Skechers Resment Chukka Boot Chukka Brown Boot Mens Casual Dress Boots, Men's, Size: 10

Founded in 1992, Skechers not only manufactures shoes in its own name but also owns many other brands. Skechers offers trendy and stylish models that look great with jeans. Skechers provides a great look but also provides comfort with a rubber sole... more

$46.36

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Timberland Arden Heights Chukka Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9.5

Timberland Arden Heights Chukka Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9.5

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$60.36

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Timberland Grantly Chukka Shoe - Men's Dark Brown Oiled Full Grain, 8.0

Timberland Grantly Chukka Shoe - Men's Dark Brown Oiled Full Grain, 8.0

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Size 8.0, Color Dark Brown Oiled Full Grain. Timberland's Grantly Men's Chukka Shoe is durable and obviously handsome, but it's harder to recognize the recycled PET polyester mesh lining and laces unless you already know about them. While the... more

$139.95

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(125,000+)
Timberland Grantly Chukka Shoe - Men's Dark Brown Oiled Full Grain, 12.0

Timberland Grantly Chukka Shoe - Men's Dark Brown Oiled Full Grain, 12.0

Free 2-Day Shipping on orders over $50!

Size 12.0, Color Dark Brown Oiled Full Grain. Timberland's Grantly Men's Chukka Shoe is durable and obviously handsome, but it's harder to recognize the recycled PET polyester mesh lining and laces unless you already know about them. While the... more

$139.95

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(125,000+)
Timberland Arden Heights Chukka Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9

Timberland Arden Heights Chukka Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$60.36

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Nike Lunar Flyknit Chukka Men US 10.5 Pink Chukka Boot, Black

Nike Lunar Flyknit Chukka Men US 10.5 Pink Chukka Boot, Black

The Nike Lunar Flyknit Chukka Men's Running Shoes are perfect for any runner on the go. Light-weight due to it's design and materials, such as the flyknit upper. Lunarlon midsole and BRS 1000 rubber outsole make sure what you're wearing is light,... more

$130.63

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Timberland Groveton Leather Chukka Red Mono Chili Pepper Mens Casual Dress Chukka Boots, Men's, Size: 8

Timberland Groveton Leather Chukka Red Mono Chili Pepper Mens Casual Dress Chukka Boots, Men's, Size: 8

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$65.36

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K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 7.5, Blue

K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 7.5, Blue

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$42.98

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K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9.5

K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9.5

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$34.36

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K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 8, Blue

K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 8, Blue

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.07

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Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 9.5, Blue

Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 9.5, Blue

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$136.36

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K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 7, Black

K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 7, Black

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.36

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Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 8, Blue

Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 8, Blue

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$136.36

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K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 6.5, Blue

K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 6.5, Blue

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$42.98

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K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 7

K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 7

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$34.36

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K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 7.5

K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 7.5

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$33.98

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K-Swiss D R Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 8, Beige

K-Swiss D R Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 8, Beige

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.36

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K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 8.5, Black

K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 8.5, Black

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.36

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K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 14

K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 14

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$34.36

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Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 10.5, Blue

Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 10.5, Blue

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$136.36

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K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 7, Blue

K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 7, Blue

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$42.36

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K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 8

K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 8

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$33.98

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K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 9, Black

K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 9, Black

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.36

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Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 8.5, Blue

Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 8.5, Blue

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$136.36

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Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 11, Blue

Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 11, Blue

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$136.36

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K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9

K-Swiss DR Cinch Chukka P Black Black Mens Casual Dress Chukka Boots, Men's, Size: 9

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$34.98

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K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 8.5, Blue

K-Swiss D R Cinch Chukka Navy White Mens Casual Dress Chukka Boots, Men's, Size: 8.5, Blue

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$42.36

FREE shipping

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K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 9.5, Black

K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 9.5, Black

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.36

FREE shipping

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K-Swiss D R Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 7.5, Beige

K-Swiss D R Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 7.5, Beige

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.36

FREE shipping

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K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 14, Black

K-Swiss DR Cinch Chukka P Taffy Gum Mens Casual Dress Chukka Boots, Men's, Size: 14, Black

K-Swiss was founded in 1966 by two brothers who moved to California to pursue their dream of starting their own footwear company. As avid skiers, they drew inspiration from leather ski boots to create the first all-leather tennis shoe. Then K-Swiss... more

$36.36

FREE shipping

go to store
Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 10, Blue

Timberland Killington Chukka Navy Full Grain Mens Casual Dress Chukka Boots, Men's, Size: 10, Blue

Timberland is one of the best brands when it comes to providing comfort and durability. Timberland provides a great look for work or for just a night out. With its comfortable cushioned sole it allows for a trendy look without lacking the comfort... more

$136.36

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Sebago Reese Chukka Men US 10.5 Brown Chukka Boot UK 10 EU 44.5

Sebago Reese Chukka Men US 10.5 Brown Chukka Boot UK 10 EU 44.5

The Sebago Reese Chukka Boots feature a Leather upper with a Round Toe . The Man-Made outsole lends lasting traction and wear. Size: 10.5. Color: Brown. Gender: Male. Age Group: Adult. more

$30.06

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Seavees 3 Eye Chukka Men US 8.5 Brown Chukka Boot, Size: 8.5 D(M) US, Cigar Pull-Up Leather

Seavees 3 Eye Chukka Men US 8.5 Brown Chukka Boot, Size: 8.5 D(M) US, Cigar Pull-Up Leather

Manufacturer: SeaVees Size: 8.5 Manufacturer Color: Cigar Leather Retail: $178.00 Condition: New with box Style Type: Chukka Boots Collection: SeaVees Shoe Width: Heel Height (Inches): 3/4 Inches Platform Height (Inches): Inches Shaft Height (Inches):... more

$72.98

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Cole Haan Grover Chukka Men US 7 Tan Chukka Boot, Brown

Cole Haan Grover Chukka Men US 7 Tan Chukka Boot, Brown

Clean lines and classic design exemplify the grover chukka Since 1928 generations of fashionable and style conscious men and women have made Cole Haan their first choice when it comes to impeccable footwear. Cole Haan shoes are synonymous with comfort,... more

$89.10

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Andrew Marc Dorchester Chukka Men US 9 Black Chukka Boot, Size: 9 D(M) US, Avion/White/Cymbal Leather

Andrew Marc Dorchester Chukka Men US 9 Black Chukka Boot, Size: 9 D(M) US, Avion/White/Cymbal Leather

The Andrew Marc Dorchester Chukka Boots feature a Leather upper with a Round Toe . The Man-Made outsole lends lasting traction and wear. Size: 9 D(M) US. Color: Avion/White/Cymbal Leather. Gender: Male. Age Group: Adult. more

$74.98

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Timberland Amherst Chukka Men US 12 Brown Chukka Boot

Timberland Amherst Chukka Men US 12 Brown Chukka Boot

The Timberland Amherst Chukka Boots feature a Canvas upper with a Round Toe . The Man-Made outsole lends lasting traction and wear. Size: 12. Color: Brown. Gender: Male. Age Group: Adult. more

$97.06

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Cole Haan Ridley Chukka Men US 13 Gray Chukka Boot, Grey

Cole Haan Ridley Chukka Men US 13 Gray Chukka Boot, Grey

Manufacturer: Cole Haan Size: 13 Medium (D) Manufacturer Color: Ironstone Retail: $188.00 Condition: New with box Style Type: Chukka Boots Collection: Cole Haan Shoe Width: Medium (D) Heel Height (Inches): 1 1/4 Inches Platform Height (Inches): Inches... more

$94.99

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Hush Puppies Style Chukka Men US 11.5 Brown Chukka Boot

Hush Puppies Style Chukka Men US 11.5 Brown Chukka Boot

The Hush Puppies Style Chukka Boots feature a Suede upper with a Round Toe . The Man-Made outsole lends lasting traction and wear. Size: 11.5. Color: Brown. Gender: Male. Age Group: Adult. more

$65.98

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