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Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 M)

Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 M)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Best Seller
Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 13 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 13 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Brooks Brothers Men's 1818 Footwear Textured Leather Chukka Sneakers | Navy | Size 7 D

Brooks Brothers Men's 1818 Footwear Textured Leather Chukka Sneakers | Navy | Size 7 D

The 1818 Footwear Collection combines Italian craftsmanship, the finest materials and timeless designs to produce versatile, comfortable shoes that form a solid foundation for the polished wardrobe. These polished chukka sneakers are crafted from... more

$298.00 $69.99

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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10

A suede spin on the Desert Boot. The coffee undertones and fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible... more

$119.95 $99.99

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TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 8.5

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 8.5

A suede spin on the Desert Boot. Fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible manufacturing via the Leather... more

$119.95 $99.99

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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 9.5

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 9.5

A suede spin on the Desert Boot. The coffee undertones and fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible... more

$119.95 $99.99

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Sorel Metro II Chukka Wp - Men's 052 9 2076781-052-9

Sorel Metro II Chukka Wp - Men's 052 9 2076781-052-9

Sorel Metro II Chukka Wp - Men's 052 9 2076781-052-9. Channeling the soul of SOREL iconic waterproof protection combines with an urban sneaker personality that's more lightweight with a versatile chukka height for warmer months. Specifications for... more

$130.00

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Sorel Metro II Chukka Wp - Men's 052 14 2076781-052-14

Sorel Metro II Chukka Wp - Men's 052 14 2076781-052-14

Sorel Metro II Chukka Wp - Men's 052 14 2076781-052-14. Channeling the soul of SOREL iconic waterproof protection combines with an urban sneaker personality that's more lightweight with a versatile chukka height for warmer months. Specifications for... more

$130.00

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Sorel Metro II Chukka Wp - Men's 286 12 2076781-286-12

Sorel Metro II Chukka Wp - Men's 286 12 2076781-286-12

Sorel Metro II Chukka Wp - Men's 286 12 2076781-286-12. Channeling the soul of SOREL iconic waterproof protection combines with an urban sneaker personality that's more lightweight with a versatile chukka height for warmer months. Specifications for... more

$130.00

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 9 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 9 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 M)

Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 M)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Astor Sneaker-sole Leather Chukka Boots

Astor Sneaker-sole Leather Chukka Boots

Men's Frye Astor Sneaker-sole Leather Chukka Boots - Brown Frye "Astor" leather chukka boots feature a rubber sneaker sole Flat heel Round toe Leather lace-up vamp Stamped logo on the side Lining: Leather Imported. more

$228.00

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Boat Chukka Sneaker

Boat Chukka Sneaker

Men's Robert Graham Boat Chukka Sneaker - Brown - Low-top sneakers Supple leather construction and a padded footbed mean all-day comfort in a stylish sneaker. more

$278.00

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Landon Chukka

Landon Chukka

Men's Helly Hansen Landon Chukka - Brown - Hi-top sneakers The Landon Chukka is a versatile shoe designed for different activities and occasions in the city. Equipped with a durable rubber cupsole, a comfort insole, and HH Max-Grip outsole, these shoes... more

$110.00

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Sorel Metro II Low Wp - Men's 052 8 2076771-052-8

Sorel Metro II Low Wp - Men's 052 8 2076771-052-8

Sorel Metro II Low Wp - Men's 052 8 2076771-052-8. Channeling the soul of SOREL iconic waterproof protection combines with an urban sneaker personality that's more lightweight with a versatile chukka height for warmer months. Specifications for Sorel... more

$120.00

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Columbia Shoes | Columbia Suede/Leather Brown Chukka Sneaker Boots Mens Size 8.5 | Color: Brown | Size: 8.5

Columbia Shoes | Columbia Suede/Leather Brown Chukka Sneaker Boots Mens Size 8.5 | Color: Brown | Size: 8.5

Gently Used! No Rips Or Tears. Smoke Free. No Box. We Carefully Package And Box Ship Asap. Reach Out With Any Questions! Pair In Photos Is The Exact Pair You Are Purchasing Deals On Multiple Pairs! more

$59.00

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Columbia Shoes | Columbia Vulc N Vent Half Dome Tan Brown Suede Leather Chukka Sneakers Shoes | Color: Brown | Size: 10.5

Columbia Shoes | Columbia Vulc N Vent Half Dome Tan Brown Suede Leather Chukka Sneakers Shoes | Color: Brown | Size: 10.5

Previously Loved In Great Condition, Some Wear On The Upper And Soles With Lots Of Life Left. Light Brown Suede Upper, Vented System, Men’s Size 10.5 Refer To Pictures And Reach Out With Any Questions! more

$39.00

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Polo By Ralph Lauren Shoes | Chukka 100 Sneaker From Polo Ralph Lauren | Color: Black | Size: 8.5

Polo By Ralph Lauren Shoes | Chukka 100 Sneaker From Polo Ralph Lauren | Color: Black | Size: 8.5

Black Men's Leather Delaney Hi Top Sneaker Black 8.5 Size:8½ Material:Genuine Leather, Genuine Suede Style:Casual Shaft Height:Ankle Closure Style:Lace-Up The Chukka 100 Sneaker From Polo Ralph Lauren Features A Soft Leather Upper Paired With A Fitted... more

$65.00

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Thomas and Vine Thomas & Vine Theo Chukka Boot - Brown - 11.5

Thomas and Vine Thomas & Vine Theo Chukka Boot - Brown - 11.5

The comfort of a sneaker meets the sharpness of chukka with the Theo by Thomas & Vine. This low-cut boot is shaped with authentic leather and textile uppers fastened by a lace-up closure. A flexible EVA/rubber outsole lined with a 12 mm Tru Comfort... more

$99.99

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Thomas and Vine Thomas & Vine Theo Chukka Boot - Black - 10.5

Thomas and Vine Thomas & Vine Theo Chukka Boot - Black - 10.5

The comfort of a sneaker meets the sharpness of chukka with the Theo by Thomas & Vine. This low-cut boot is shaped with authentic leather and textile uppers fastened by a lace-up closure. A flexible EVA/rubber outsole lined with a 12 mm Tru Comfort... more

$99.99

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Thomas and Vine Thomas & Vine Theo Chukka Boot - Black - 12

Thomas and Vine Thomas & Vine Theo Chukka Boot - Black - 12

The comfort of a sneaker meets the sharpness of chukka with the Theo by Thomas & Vine. This low-cut boot is shaped with authentic leather and textile uppers fastened by a lace-up closure. A flexible EVA/rubber outsole lined with a 12 mm Tru Comfort... more

$99.99

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Carhartt Force 5" Nano Toe Lightweight Sneaker Boot - Mens 9 Black Boot Medium

Carhartt Force 5" Nano Toe Lightweight Sneaker Boot - Mens 9 Black Boot Medium

*Chukka work boot from Carhartt *Black high abrasion resistant 1200D fabric and black leather *Nano Composite safety toe cap is lightweight, non-metallic, and non-conductive to heat or cold *Safety toe meets or exceeds ASTM 2413-18 standards *Insite®... more

$144.95

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Carhartt Force 5" Nano Toe Lightweight Sneaker Boot - Mens 10.5 Black Boot Medium

Carhartt Force 5" Nano Toe Lightweight Sneaker Boot - Mens 10.5 Black Boot Medium

*Chukka work boot from Carhartt *Black high abrasion resistant 1200D fabric and black leather *Nano Composite safety toe cap is lightweight, non-metallic, and non-conductive to heat or cold *Safety toe meets or exceeds ASTM 2413-18 standards *Insite®... more

$144.95

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Carhartt Force 5" Nano Toe Lightweight Sneaker Boot - Mens 12 Black Boot W

Carhartt Force 5" Nano Toe Lightweight Sneaker Boot - Mens 12 Black Boot W

*Chukka work boot from Carhartt *Black high abrasion resistant 1200D fabric and black leather *Nano Composite safety toe cap is lightweight, non-metallic, and non-conductive to heat or cold *Safety toe meets or exceeds ASTM 2413-18 standards *Insite®... more

$144.95

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Skechers Men's Vigor 2.0 - Trait Sneaker | Size 9.5 Wide | Taupe/Black | Leather/Textile/Synthetic

Skechers Men's Vigor 2.0 - Trait Sneaker | Size 9.5 Wide | Taupe/Black | Leather/Textile/Synthetic

Get even more sporty comfort out of Skechers Vigor 2.0 - Trait. This lace-up athletic style features a trubuck leather, synthetic and mesh fabric upper with cushioned Memory Foam insole. | Skechers Men's Vigor 2.0 - Trait Sneaker | Size 9.5 Wide |... more

$75.00 $52.99

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Skechers Men's Energy - After Burn Sneaker | Size 10.0 Wide | White/Navy | Leather/Synthetic/Textile

Skechers Men's Energy - After Burn Sneaker | Size 10.0 Wide | White/Navy | Leather/Synthetic/Textile

Hit the track with breakneck speed in Skechers Energy - After Burn. This lace-up sporty athletic sneaker features a smooth leather and mesh upper with a cushioned insole. | Skechers Men's Energy - After Burn Sneaker | Size 10.0 Wide | White/Navy |... more

$75.00

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Skechers Men's Energy - After Burn Sneaker | Size 12.0 | White/Navy | Leather/Synthetic/Textile

Skechers Men's Energy - After Burn Sneaker | Size 12.0 | White/Navy | Leather/Synthetic/Textile

Hit the track with breakneck speed in Skechers Energy - After Burn. This lace-up sporty athletic sneaker features a smooth leather and mesh upper with a cushioned insole. | Skechers Men's Energy - After Burn Sneaker | Size 12.0 | White/Navy |... more

$75.00

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Danner Pine Grove Chukka Hiking Shoes Leather Men's, Roasted Pecan SKU - 360144

Danner Pine Grove Chukka Hiking Shoes Leather Men's, Roasted Pecan SKU - 360144

The Danner Pine Grove Chukka Leather Hiking Shoes provide non-marking, oil-and-slip-resistant outsoles to offer superior traction in urban environments. The shoes are completely recraftable, including lace hardware, outsole, midsole, toe cap, heel... more

$239.95

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 10 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 10 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 M)

Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 M)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 11 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 11 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 7

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 7

A suede spin on the Desert Boot. The coffee undertones and fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible... more

$119.95 $99.99

FREE shipping

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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 12

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 12

A suede spin on the Desert Boot. The coffee undertones and fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible... more

$119.95 $99.99

FREE shipping

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TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 14

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 14

A suede spin on the Desert Boot. Fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible manufacturing via the Leather... more

$119.95 $99.99

FREE shipping

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TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10.5

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10.5

A suede spin on the Desert Boot. Fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible manufacturing via the Leather... more

$119.95 $99.99

FREE shipping

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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 11.5

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 11.5

A suede spin on the Desert Boot. The coffee undertones and fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible... more

$119.95 $99.99

FREE shipping

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TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 9

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 9

A suede spin on the Desert Boot. Fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible manufacturing via the Leather... more

$119.95 $99.99

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