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Men's Sperry Top-Sider Gold Windsor Lug Chukka Boot, Taupe Suede
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Men's Sperry Top-Sider Gold Windsor Lug Chukka Boot, Taupe Suede

As stylish as it is comfortable, the Sperry Top-Sider Gold Windsor Lug Chukka Boot will go with any casual outfit. This boot features a removable OrthoLite footbed that offers moisture-wicking comfort, and a plantation crepe outsole that ensures...

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Men's Sperry Top-Sider Gold Windsor Lug Chukka Boot, Brown Full Grain Leather
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Men's Sperry Top-Sider Gold Windsor Lug Chukka Boot, Brown Full Grain Leather

As stylish as it is comfortable, the Sperry Top-Sider Gold Windsor Lug Chukka Boot will go with any casual outfit. This boot features a removable OrthoLite footbed that offers moisture-wicking comfort, and a plantation crepe outsole that ensures...

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Men's Steve Madden Harver Chukka Boot, Tan Leather
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Men's Steve Madden Harver Chukka Boot, Tan Leather

Classic and stylish, the Steve Madden Harver Chukka Boot will become your go-to boot. Its rich leather upper has enough finesse for your everyday look. Chukka boot design Lace-up closure. Sizes: 7 M, 9.5 M, 14 M, 10 M, 12 M, 7.5 M, 11 M, 8.5 M, 10.5...

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Men's Florsheim NDNS Chukka Boot, Black Leather
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Men's Florsheim NDNS Chukka Boot, Black Leather

The NDNS Chukka Boot is both practical and tasteful, an unsurpassable combination. With its supremely structured last, Memory Foam footbed, and non-slip outsole, as well as its waterproof leather, the NDNS Chukka Boot will far outlive its...

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Men's Steve Madden Harver Chukka Boot, Black Leather
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Men's Steve Madden Harver Chukka Boot, Black Leather

Classic and stylish, the Steve Madden Harver Chukka Boot will become your go-to boot. Its rich leather upper has enough finesse for your everyday look. Chukka boot design Lace-up closure. Sizes: 11.5 M, 13 M, 12 M, 11 M, 8.5 M, 9 M, 9.5 M, 10.5 M,...

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Men's Steve Madden Harver Chukka Boot, Cognac Leather
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Men's Steve Madden Harver Chukka Boot, Cognac Leather

Classic and stylish, the Steve Madden Harver Chukka Boot will become your go-to boot. Its rich leather upper has enough finesse for your everyday look. Chukka boot design Lace-up closure. Sizes: 13 M, 8.5 M, 7.5 M, 7 M, 9.5 M, 14 M, 10.5 M, 9 M, 11...

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Men's Rockport Rydley Chukka Boot, Taupe Nubuck
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Men's Rockport Rydley Chukka Boot, Taupe Nubuck

Modern and comfortable, the Rockport Rydley Chukka Boot is a must-have in your footwear collection. Featuring a lightweight yet durable EVA outsole, this chukka boot makes every step feels effortless, making walking easier and more enjoyable than...

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Men's Stacy Adams Dabney Plain Toe Chukka Boot 24977, Chestnut Suede
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Men's Stacy Adams Dabney Plain Toe Chukka Boot 24977, Chestnut Suede

An urbane chukka that conveys a sense of sophistication, the Dabney Chukka boot is characterized by its oiled suede upper. This material provides a rare texture and look for an elegant, yet casual appearance that is hard to match. Sizes: 10 W, 7.5...

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Men's Robert Talbott Chino Chukka Boot, Oak Leather
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Men's Robert Talbott Chino Chukka Boot, Oak Leather

The Chino Chukka Boot from Robert Talbott is a 2 eyelet chukka boot with burnished upper and fully rubber outsole. 2 eyelet Rubber sole. Sizes: 8.5 M, 11 M, 12 M, 13 M, 9.5 M, 9 M, 10 M, 11.5 M, 10.5 M; Color: Oak Leather. Gender: Male. Age Group:...

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Men's UGG Maksim Chukka Boot, Tamarind Suede
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Men's UGG Maksim Chukka Boot, Tamarind Suede

The UGG Maksim Chukka Boot combines classic UGG comfort with a relaxed chukka silhouette that's perfect for downtime. Suede UGGpure wool insole EVA outsole. Sizes: 18 M, 17 M, 15 M, 16 M; Color: Tamarind Suede. Gender: Male. Age Group: Adult.

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Men's UGG Maksim Chukka Boot, Black Suede
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Men's UGG Maksim Chukka Boot, Black Suede

The UGG Maksim Chukka Boot combines classic UGG comfort with a relaxed chukka silhouette that's perfect for downtime. Suede UGGpure wool insole EVA outsole. Sizes: 15 M, 17 M, 16 M, 18 M; Color: Black Suede. Gender: Male. Age Group: Adult.

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Men's Pikolinos Lugo Chukka Boot M1F-8093, Olmo Leather
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Men's Pikolinos Lugo Chukka Boot M1F-8093, Olmo Leather

With clean lines and a classic look, the Lugo Chukka Boot from Pikolinos is a confident choice for your dressy attire. 3-eye chukka Plain toe Eco-friendly, vegetable-based dye Chromium free 100% soft leather. Sizes: 45 M, 42 M, 43 M; Color: Olmo...

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Men's Robert Talbott Chino Chukka Boot, Brown Pebble Leather
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Men's Robert Talbott Chino Chukka Boot, Brown Pebble Leather

The Chino Chukka Boot from Robert Talbott is a 2 eyelet chukka boot with burnished upper and fully rubber outsole. 2 eyelet Rubber sole. Sizes: 10.5 M, 13 M, 9 M, 11 M, 12 M, 9.5 M, 11.5 M, 10 M; Color: Brown Pebble Leather. Gender: Male. Age Group:...

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Men's UGG Maksim Chukka Boot, Grizzly Full Grain Leather
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Men's UGG Maksim Chukka Boot, Grizzly Full Grain Leather

The UGG Maksim Chukka Boot combines classic UGG comfort with a relaxed chukka silhouette that's perfect for downtime. Suede UGGpure wool insole EVA outsole. Sizes: 9 M; Color: Grizzly Full Grain Leather. Gender: Male. Age Group: Adult.

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Men's Stacy Adams Dabney Plain Toe Chukka Boot 24977, Navy Suede
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Men's Stacy Adams Dabney Plain Toe Chukka Boot 24977, Navy Suede

An urbane chukka that conveys a sense of sophistication, the Dabney Chukka boot is characterized by its oiled suede upper. This material provides a rare texture and look for an elegant, yet casual appearance that is hard to match. Sizes: 13 M, 9.5...

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Vans Chukka DX SF Sneaker, Surf Check Black Canvas/White
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Vans Chukka DX SF Sneaker, Surf Check Black Canvas/White

The Vans Chukka DX SF builds upon the original Chukka Boot silhouette by combining durable uppers with comfortable UltraCush sockliners for long lasting comfort, and signature waffle rubber outsoles. Chukka boot styling UltraCush Lite midsole...

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Children's Old West Chukka Outdoor Boot, Brown Leather
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Children's Old West Chukka Outdoor Boot, Brown Leather

The Old West Boots Chukka Outdoor Boot is a classic, rugged chukka boot with a removable cushioned insole. Genuine leather Padded collar provides comfort for all day wear Lace up closures for customized and secure fit Manmade soft cushioned lining...

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Women's Superfeet Olympia Chukka Boot, Black/Turtledove
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Women's Superfeet Olympia Chukka Boot, Black/Turtledove

Go from busy office hours to fun weekend outings in the classic comfort of the Superfeet Olympia Chukka Boot. Featuring the Supercork insole, this men's chukka boot offers enhanced support and shock-absorption for dynamic comfort all day long....

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Men's Dr. Scholl's Original Collection Freewill Chukka Boot, Brown Leather
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Men's Dr. Scholl's Original Collection Freewill Chukka Boot, Brown Leather

You like to move, and so does the Dr. Scholl's Freewill Chukka Boot. Combining the style of a chukka boot with an athletic feel, the white sole makes it a style standout. Memory Foam Cool Fit insole Aegis Microbe Shield controls odor Rubber...

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Men's Rockport Rydley Chukka Boot, Dark Bitter Chocolate Nubuck
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Men's Rockport Rydley Chukka Boot, Dark Bitter Chocolate Nubuck

Modern and comfortable, the Rockport Rydley Chukka Boot is a must-have in your footwear collection. Featuring a lightweight yet durable EVA outsole, this chukka boot makes every step feels effortless, making walking easier and more enjoyable than...

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Men's Stacy Adams Delaney Chukka Boot 25053, Brown Burnished Leather/Suede
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Men's Stacy Adams Delaney Chukka Boot 25053, Brown Burnished Leather/Suede

The Stacy Adams Delaney Chukka Boot is constructed with the finest craftsmanship, featuring hand-burnished leather and suede. This comfortable chukka can be worn day in and day out, and never fails to impress. Features Plain toe chukka Hand...

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Women's Superfeet Olympia Chukka Boot, Black Iris/Turtledove
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Women's Superfeet Olympia Chukka Boot, Black Iris/Turtledove

Go from busy office hours to fun weekend outings in the classic comfort of the Superfeet Olympia Chukka Boot. Featuring the Supercork insole, this men's chukka boot offers enhanced support and shock-absorption for dynamic comfort all day long....

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Men's Superfeet Olympia Chukka Boot, Chipmunk
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Men's Superfeet Olympia Chukka Boot, Chipmunk

Go from busy office hours to fun weekend outings in the classic comfort of the Superfeet Olympia Chukka Boot. Featuring the Supercork insole, this women's chukka boot offers enhanced support and shock-absorption for dynamic comfort all day...

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Men's Stacy Adams Dabney Plain Toe Chukka Boot 24977, Black Suede Suede
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Men's Stacy Adams Dabney Plain Toe Chukka Boot 24977, Black Suede Suede

An urbane chukka that conveys a sense of sophistication, the Dabney Chukka boot is characterized by its oiled suede upper. This material provides a rare texture and look for an elegant, yet casual appearance that is hard to match. Sizes: 10 M, 10 W,...

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Men's Dr. Scholl's Original Collection Freewill Chukka Boot, Taupe Waxy Suede
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Men's Dr. Scholl's Original Collection Freewill Chukka Boot, Taupe Waxy Suede

You like to move, and so does the Dr. Scholl's Freewill Chukka Boot. Combining the style of a chukka boot with an athletic feel, the white sole makes it a style standout. Memory Foam Cool Fit insole Aegis Microbe Shield controls odor Rubber...

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Men's Dr. Scholl's Original Collection Freewill Chukka Boot, Grey Cow Suede
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Men's Dr. Scholl's Original Collection Freewill Chukka Boot, Grey Cow Suede

You like to move, and so does the Dr. Scholl's Freewill Chukka Boot. Combining the style of a chukka boot with an athletic feel, the white sole makes it a style standout. Memory Foam Cool Fit insole Aegis Microbe Shield controls odor Rubber...

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Men's UGG Neumel Chukka Boot, Stout Crackle Grain Leather
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Men's UGG Neumel Chukka Boot, Stout Crackle Grain Leather

The UGG Neumel Chukka Boot is a sturdy, casual chukka with a plush sheepskin lining and leather upper. Leather upper Sheepskin lining Cushioning foam insole with UGGpure wool Lightweight, flexible EVA outsole. Sizes: 8 M, 7 M; Color: Stout Crackle...

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Boys' Florsheim Curb Chukka Boot, Jr, Black Synthetic
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Boys' Florsheim Curb Chukka Boot, Jr, Black Synthetic

Striking the perfect balance between style and comfort, the Florsheim Curb Chukka Boot Jr. is an effortless addition to a boy's everyday look. This shoe features a subtle design that pairs easily with his favorite pair of jeans or khakis....

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Boys' Florsheim Curb Chukka Boot, Jr, Cognac Synthetic
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Boys' Florsheim Curb Chukka Boot, Jr, Cognac Synthetic

Striking the perfect balance between style and comfort, the Florsheim Curb Chukka Boot Jr. is an effortless addition to a boy's everyday look. This shoe features a subtle design that pairs easily with his favorite pair of jeans or khakis....

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Men's Georgia Boot GB00257 Wedge Chukka Composite Toe Work Boot, Barracuda Gold Leather
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Men's Georgia Boot GB00257 Wedge Chukka Composite Toe Work Boot, Barracuda Gold Leather

The Georgia Boot Wedge Chukka Composite Toe Work Boot is a sturdy and dependable companion for the jobsite. Crafted from the SPR leather, this moisture-wicking boot protects from acids and chemicals found on farms and construction sites. The covered...

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Men's Superfeet Olympia Chukka Boot, Black/Magnet
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Men's Superfeet Olympia Chukka Boot, Black/Magnet

Go from busy office hours to fun weekend outings in the classic comfort of the Superfeet Olympia Chukka Boot. Featuring the Supercork insole, this women's chukka boot offers enhanced support and shock-absorption for dynamic comfort all day...

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Boys' Florsheim Getaway Chukka Boot, Jr. II, Cognac Leather
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Boys' Florsheim Getaway Chukka Boot, Jr. II, Cognac Leather

The classic design and easy comfort of the Florsheim Getaway Chukka Boot Jr. II ensures that these shoes will soon become a new favorite. The Chukka features durable construction for long-term wearability. Smooth leather upper, clean cut design....

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Men's Pikolinos Salou Chukka Boot M9M-8148, Olmo Leather
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Men's Pikolinos Salou Chukka Boot M9M-8148, Olmo Leather

Featuring an elegant design, the Salou Chukka Boot M9M-8148 is an essential style for every man's wardrobe. Ankle boot silhouette Lace up closure. Sizes: 41 M, 43 M, 44 M, 46 M, 45 M; Color: Olmo Leather. Gender: Male. Age Group: Adult.

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Men's UGG Freamon Chukka Boot, Redwood
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Men's UGG Freamon Chukka Boot, Redwood

For a durable, streamlined style, step out in the men's UGG Freamon Chukka Boot. Designed with a waterproof suede upper and a soft UGGpure canvas lined insole. This UGG Chukka Boot offers Twinsole interchangeable insoles so that you can adapt...

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Men's Pikolinos Salou Chukka Boot M9M-8148, Black Leather
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Men's Pikolinos Salou Chukka Boot M9M-8148, Black Leather

Featuring an elegant design, the Salou Chukka Boot M9M-8148 is an essential style for every man's wardrobe. Ankle boot silhouette Lace up closure. Sizes: 41 M, 45 M, 42 M, 43 M, 44 M, 46 M; Color: Black Leather. Gender: Male. Age Group: Adult.

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Men's Florsheim Castellano Chukka, Black Leather
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Men's Florsheim Castellano Chukka, Black Leather

A refined chukka is a must-have for any proud shoe collector. The Castellano Chukka Boot is a tasteful shoe with a classic silhouette, carefully constructed to distinguish you among the sea of oxfords and saddles. It's time to up your game....

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Men's Rockport Sharp & Ready Chukka Boot, Brown/Brown Leather
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Men's Rockport Sharp & Ready Chukka Boot, Brown/Brown Leather

A refreshing take on a timeless classic, the Rockport Sharp & Ready Chukka Boot will complement any ensemble. This lightweight chukka boot features latex foam cushioning that helps reduce foot fatigue, ensuring a comfortable fit all day. Latex...

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Men's Florsheim Hamilton Chukka Boot, Brown
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Men's Florsheim Hamilton Chukka Boot, Brown

The Florsheim Hamilton Chukka Boot is a classic dress boot with a modern edge, constructed from our finest materials. Clean lines and simple perforations define this handsome member of the Imperial line. Sheepskin linings XL Extralight sole...

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Men's Superfeet Douglas Chukka Boot, Black/Brindle
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Men's Superfeet Douglas Chukka Boot, Black/Brindle

The Superfeet Douglas Chukka Boot will create an adventure-ready look perfect for all day, every day. This waterproof chukka boot features the Supercork insole that not only offers enhanced arch support but also provides maximum shock-absorption in...

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Men's Cole Haan Kennedy Grand Chukka Waterproof Boot, Woodbury Waterproof Leather
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Men's Cole Haan Kennedy Grand Chukka Waterproof Boot, Woodbury Waterproof Leather

The Cole Haan Kennedy Grand Chukka Waterproof Boot is a classic chukka boot made from waterproof leather. The innovative rubber unit bottom has been cored out and filled with proprietary Grand OS cushioning foam for comfort, lightness or weight and...

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Men's Superfeet Douglas Chukka Boot, Chipmunk/Turtledove
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Men's Superfeet Douglas Chukka Boot, Chipmunk/Turtledove

The Superfeet Douglas Chukka Boot will create an adventure-ready look perfect for all day, every day. This waterproof chukka boot features the Supercork insole that not only offers enhanced arch support but also provides maximum shock-absorption in...

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Men's Rockport Sharp & Ready Chukka Boot, Black Leather
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Men's Rockport Sharp & Ready Chukka Boot, Black Leather

A refreshing take on a timeless classic, the Rockport Sharp & Ready Chukka Boot will complement any ensemble. This lightweight chukka boot features latex foam cushioning that helps reduce foot fatigue, ensuring a comfortable fit all day. Latex...

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Men's Florsheim Castellano Chukka, Brown Leather
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Men's Florsheim Castellano Chukka, Brown Leather

A refined chukka is a must-have for any proud shoe collector. The Castellano Chukka Boot is a tasteful shoe with a classic silhouette, carefully constructed to distinguish you among the sea of oxfords and saddles. It's time to up your game....

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Men's Eastland 1955 Edition Hull 1955 Chukka Boot, Khaki Suede
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Men's Eastland 1955 Edition Hull 1955 Chukka Boot, Khaki Suede

The Eastland 1955 Hull Chukka Boot is a 2-eye chukka boot selected from Eastland's design archives and crafted from the finest components available. It's handcrafted by skilled shoemakers using a hand sewn stitch out construction. Premium...

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Men's Cole Haan Kennedy Grand Chukka Waterproof Boot, Black Waterproof Leather
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Men's Cole Haan Kennedy Grand Chukka Waterproof Boot, Black Waterproof Leather

The Cole Haan Kennedy Grand Chukka Waterproof Boot is a classic chukka boot made from waterproof leather. The innovative rubber unit bottom has been cored out and filled with proprietary Grand OS cushioning foam for comfort, lightness or weight and...

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Men's Eastland 1955 Edition Hull 1955 Chukka Boot, Brown Leather
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Men's Eastland 1955 Edition Hull 1955 Chukka Boot, Brown Leather

The Eastland 1955 Hull Chukka Boot is a 2-eye chukka boot selected from Eastland's design archives and crafted from the finest components available. It's handcrafted by skilled shoemakers using a hand sewn stitch out construction. Premium...

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Men's Rockport Sharp & Ready Chukka Boot, Tobacco Suede
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Men's Rockport Sharp & Ready Chukka Boot, Tobacco Suede

A refreshing take on a timeless classic, the Rockport Sharp & Ready Chukka Boot will complement any ensemble. This lightweight chukka boot features latex foam cushioning that helps reduce foot fatigue, ensuring a comfortable fit all day. Latex...

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Men's Steve Madden Melded Chukka Boot, Dark Brown Burnished Nubuck Leather
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Men's Steve Madden Melded Chukka Boot, Dark Brown Burnished Nubuck Leather

The Steve Madden Melded Chukka Boot is a classic, rugged ankle boot that can be dressed up or down. Polyurethane insole Rubber outsole. Sizes: 10.5 M, 11.5 M, 12 M, 10 M; Color: Dark Brown Burnished Nubuck Leather. Gender: Male. Age Group: Adult.

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Men's Lucchese Bootmaker Evan Chukka Boot, Black Cherry Royal Calf
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Men's Lucchese Bootmaker Evan Chukka Boot, Black Cherry Royal Calf

Take your stylish look up a notch with the Lucchese Bootmaker Evan Chukka Boot. This classic, handmade boot features a leather insole and outsole. Handcrafted Leather outsole Made in USA. Sizes: 10 D; Color: Black Cherry Royal Calf. Gender: Male....

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Women's Ariat Cruiser Lace Chukka Boot, Brown Bomber Leather
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Women's Ariat Cruiser Lace Chukka Boot, Brown Bomber Leather

Slip on the Ariat Cruiser Lace Chukka Boot for everyday comfort and style. This lace-up boot features the Duratread outsole that provides maximum wear resistance, for lasting performance, protection, and flexibility. Duratread outsole EVA midsole....

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Men's Lucchese Bootmaker Evan Chukka Boot, Light Brown Royal Calf
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Men's Lucchese Bootmaker Evan Chukka Boot, Light Brown Royal Calf

Take your stylish look up a notch with the Lucchese Bootmaker Evan Chukka Boot. This classic, handmade boot features a leather insole and outsole. Handcrafted Leather outsole Made in USA. Sizes: 11 D, 10 D, 12 D, 13 D, 8 D; Color: Light Brown Royal...

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Men's Caterpillar Mitch Chukka Boot, Dark Beige Leather
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Men's Caterpillar Mitch Chukka Boot, Dark Beige Leather

Whatever the occasion, from a walk on the trail to a trip into the office, the Mitch Chukka Boot from Caterpillar covers all your bases. The minimalistic design in handsome leather gives this classic chukka a casual style, making it an easy addition...

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Men's Steve Madden Lost Chukka Slip On, Taupe Suede
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Men's Steve Madden Lost Chukka Slip On, Taupe Suede

Steve Madden created the Lost Chukka Slip On with a cool casual low-profile chukka style featuring moc toe stitching accents with a modern contrast colored bottom that goes from workdays to the weekend with ease. Suede Chukka boot styled low-profile...

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Men's Steve Madden Lost Chukka Slip On, Cognac Suede
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Men's Steve Madden Lost Chukka Slip On, Cognac Suede

Steve Madden created the Lost Chukka Slip On with a cool casual low-profile chukka style featuring moc toe stitching accents with a modern contrast colored bottom that goes from workdays to the weekend with ease. Suede Chukka boot styled low-profile...

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Women's Converse Chuck Taylor All Star Ox Mono Low Sneaker, Aegean Storm/Aegean Storm/Gold
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Women's Converse Chuck Taylor All Star Ox Mono Low Sneaker, Aegean Storm/Aegean Storm/Gold

The lightweight Converse Chuck Taylor All Star Ox Mono Low Sneaker is perfect for any casual outing, from music fests to fun family cookouts. This moisture-wicking cap-toe sneaker is designed with an OrthoLite insole that ensures breathability and...

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Men's Rockport Dustyn Chukka Boot, New Caramel Leather
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Men's Rockport Dustyn Chukka Boot, New Caramel Leather

The Rockport Dustyn Chukka Boot is designed for the man on the go. Featuring the shock-absorbing truTECH system, Hydro-Shield 8482; waterproof construction, and slip-resistant rubber outsole, this chukka boot will have you ready for whatever the day...

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Men's Rockport Sharp & Ready Chukka Boot, Castlerock Grey Leather
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Men's Rockport Sharp & Ready Chukka Boot, Castlerock Grey Leather

A refreshing take on a timeless classic, the Rockport Sharp & Ready Chukka Boot will complement any ensemble. This lightweight chukka boot features latex foam cushioning that helps reduce foot fatigue, ensuring a comfortable fit all day. Latex...

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Men's Florsheim Casey Chukka Boot, Black Leather
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Men's Florsheim Casey Chukka Boot, Black Leather

Sometimes less is more. Why would you want something complicated when there's a simple shoe solution to all of your wardrobe problems? With its smooth leather and classic, clean design, the Casey Chukka Boot is all you need. Florsheim Mens Size...

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Men's Steve Madden Melded Chukka Boot, Dark Tan Burnished Nubuck Leather
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Men's Steve Madden Melded Chukka Boot, Dark Tan Burnished Nubuck Leather

The Steve Madden Melded Chukka Boot is a classic, rugged ankle boot that can be dressed up or down. Polyurethane insole Rubber outsole. Sizes: 10.5 M, 9 M, 13 M, 10 M, 11 M, 11.5 M, 12 M, 9.5 M; Color: Dark Tan Burnished Nubuck Leather. Gender:...

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Women's Timberland FlyRoam Go Lace Chukka Boot, Pure Cashmere Escape/Natural Sandune
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Women's Timberland FlyRoam Go Lace Chukka Boot, Pure Cashmere Escape/Natural Sandune

Be ready to spring at a moment's notice with the Timberland FlyRoam Go Lace Chukka Boot. Thanks to the Aerocore energy system, this lightweight chukka boot ensures cushioned comfort with every step. In addition, the 34% recycled rubber outsole...

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