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Trask Men's Brady Chukka Boot, Saddle Tan, 9 M US

Trask Men's Brady Chukka Boot, Saddle Tan, 9 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$223.34

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Trask Men's Brady Chukka Boot, Saddle Tan, 13 M US

Trask Men's Brady Chukka Boot, Saddle Tan, 13 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$223.34

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Best Seller
Trask Men's Brady Chukka Boot, Saddle Tan, 8.5 M US

Trask Men's Brady Chukka Boot, Saddle Tan, 8.5 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$223.34

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Hugo Men's Boheme Water-Resistant Suede Desert Boots - Blue 11

Hugo Men's Boheme Water-Resistant Suede Desert Boots - Blue 11

Rich Italian suede leather creates the luxurious texture of these handsome chukka boots with a water-resistant finish from Hugo Boss. more

$245.00

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Hugo Men's Boheme Water-Resistant Suede Desert Boots - Blue 10

Hugo Men's Boheme Water-Resistant Suede Desert Boots - Blue 10

Rich Italian suede leather creates the luxurious texture of these handsome chukka boots with a water-resistant finish from Hugo Boss. more

$245.00

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Hugo Men's Boheme Water-Resistant Suede Desert Boots - Blue 7

Hugo Men's Boheme Water-Resistant Suede Desert Boots - Blue 7

Rich Italian suede leather creates the luxurious texture of these handsome chukka boots with a water-resistant finish from Hugo Boss. more

$245.00

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Sam Chukka - Black - Frye Boots

Sam Chukka - Black - Frye Boots

Frye Sam Chukka - The Frye Sam Chukka offers a clean handsome style that easily complements outfits for the office and more casual events. High-quality Italian calf suede upper. Leather has been chrome tanned in the UK and oiled for a casual feel that... more

$298.00 $180.00

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Men's Bruno Magli Chavez Italian Suede Chukka Boot - Cognac Suede Boots

Men's Bruno Magli Chavez Italian Suede Chukka Boot - Cognac Suede Boots

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A soft Italian suede upper creates a breathtaking makeover in the classic Chavez chukka boot from Bruno Magli. Italian suede upper 1-inch heel Natural leather welt Snip toe Lace-up closure Italian nappa leather lining Natural plantation crepe rubber... more

$334.95

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shoes.com

(175,000+)
Men's Vince Gregory Leather Chukka Boot - Black Deerskin Leather Boots

Men's Vince Gregory Leather Chukka Boot - Black Deerskin Leather Boots

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A rich Italian leather upper lends an air of distinction to the Vince Gregory Chukka Boot, an of-the moment style. Italian deerskin leather upper Welted details Double eyelet leather laces Italian leather crepe sole Made in Italy. more

$325.00 $199.95

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shoes.com

(175,000+)
Gregory Leather Chukka Boot - Black - Vince Boots

Gregory Leather Chukka Boot - Black - Vince Boots

Vince Gregory Leather Chukka Boot - A rich Italian leather upper lends an air of distinction to the Vince Gregory Chukka Boot, an of-the moment style. Italian deerskin leather upper. Welted details. Double eyelet leather laces. Italian leather crepe... more

$325.00 $200.00

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Sullivan Chukka Leather Boots - Brown - John Varvatos Boots

Sullivan Chukka Leather Boots - Brown - John Varvatos Boots

John Varvatos Sullivan Chukka Leather Boots - Stacked heel chukka boots crafted from Italian leather. Stacked heel, 1.25". Shaft, 3.5". Lace-up closure. Leather lining and sole. Made in Italy. more

$498.00 $250.00

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Frye Austin Feather Leather Pull-On Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Frye Austin Feather Leather Pull-On Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Sizing: True to size. M=standard width. Almond toe. Stitched feather designed vamp. Allover contrast stitched design. Italian leather construction. Side pull-tabs. Goodyear welt stitching. Pull-on. Lightly padded footbed. Approx. 11.5" shaft height,... more

$458.00 $229.97

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Frye Austin Feather Leather Pull-On Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Frye Austin Feather Leather Pull-On Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Sizing: True to size. M=standard width. Almond toe. Stitched feather designed vamp. Allover contrast stitched design. Italian leather construction. Side pull-tabs. Goodyear welt stitching. Pull-on. Lightly padded footbed. Approx. 11.5" shaft height,... more

$458.00 $229.97

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Frye Austin Feather Leather Pull-On Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Frye Austin Feather Leather Pull-On Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Sizing: True to size. M=standard width. Almond toe. Stitched feather designed vamp. Allover contrast stitched design. Italian leather construction. Side pull-tabs. Goodyear welt stitching. Pull-on. Lightly padded footbed. Approx. 11.5" shaft height,... more

$458.00 $229.97

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Men's Florsheim Jet Chukka - Black Smooth Leather Boots

Men's Florsheim Jet Chukka - Black Smooth Leather Boots

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The Florsheim Jet Chukka is an Italian inspired demi boot. This elongated Euro style dress boot is cobbled with the distinguished man in mind. This boot features a breathable leather lining, a full leather non-removable footbed, and a furniture finish... more

$135.00 $81.00

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shoes.com

(175,000+)
Tod's Men's Leather Chukka Desert Boots Shoes Black

Tod's Men's Leather Chukka Desert Boots Shoes Black

Tod's signature shoes are handmade by Italian artisans using century-old techniques. This pair is finished with the brand's iconic T logo - a chic and practical choice for busy days in the city or on vacation. more

$700.00 $418.95

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Tod's Men's Leather Chukka Desert Boots Shoes Black

Tod's Men's Leather Chukka Desert Boots Shoes Black

Tod's signature shoes are handmade by Italian artisans using century-old techniques. This pair is finished with the brand's iconic T logo - a chic and practical choice for busy days in the city or on vacation. more

$700.00 $418.95

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Tod's Men's Leather Chukka Desert Boots Shoes Black

Tod's Men's Leather Chukka Desert Boots Shoes Black

Tod's signature shoes are handmade by Italian artisans using century-old techniques. This pair is finished with the brand's iconic T logo - a chic and practical choice for busy days in the city or on vacation. more

$700.00 $418.95

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To Boot New York Corvera Chukka Boot (Men)

To Boot New York Corvera Chukka Boot (Men)

Richly textured, buttery-soft deerskin leather defines a charming Italian chukka boot with smart arch support. Style Name:To Boot New York Corvera Chukka Boot (Men). Style Number: 5600067. Available in stores. more

$350.00

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To Boot New York Corvera Chukka Boot (Men)

To Boot New York Corvera Chukka Boot (Men)

Richly textured, buttery-soft deerskin leather defines a charming Italian chukka boot with smart arch support. Style Name:To Boot New York Corvera Chukka Boot (Men). Style Number: 5600067. Available in stores. more

$350.00

FREE shipping

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To Boot New York Corvera Chukka Boot (Men)

To Boot New York Corvera Chukka Boot (Men)

Richly textured, buttery-soft deerskin leather defines a charming Italian chukka boot with smart arch support. Style Name:To Boot New York Corvera Chukka Boot (Men). Style Number: 5600067. Available in stores. more

$350.00

FREE shipping

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Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 Wide, Model GB1222

Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 Wide, Model GB1222

These Georgia Farm & Ranch Chukka work boots are ideal for accomplishing daily tasks on the farm. The uppers are built with rugged SPR full-grain leather, which resists caustic chemicals and barnyard acids and is much stronger than traditional... more

$124.99

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Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 1/2 Wide, Model GB1222

Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 1/2 Wide, Model GB1222

These Georgia Farm & Ranch Chukka work boots are ideal for accomplishing daily tasks on the farm. The uppers are built with rugged SPR full-grain leather, which resists caustic chemicals and barnyard acids and is much stronger than traditional... more

$124.99

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Italian Military Surplus Canvas Gaiters 2 Pairs New, Grey

Italian Military Surplus Canvas Gaiters 2 Pairs New, Grey

Blaze the backcountry with no fear of brambles, thorns and whippy weeds. Keep boots free of debris, too. Armor up with these well-made Gaiters. Includes 2 sets so you'll have a spare. Olive Drab heavyweight canvas body Elastic cuff at top Leather at... more

$19.99

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Fin & Feather Men's Chukka Brown Boot 13 E

Fin & Feather Men's Chukka Brown Boot 13 E

*Footwear designed to take you off the trail where the going can be treacherous *Tumbled full grain leather upper *Multi-layer CUSH-N-EEZ® construction for added stability and shock-absorbency *Velvet-eez® cushioned innersole *DRI-LEX® two-zone comfort... more

$125.95

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ShoeMall.com

(50,000+)
Work America Men's Work Chukka Black Boot 13 E

Work America Men's Work Chukka Black Boot 13 E

*WORK AMERICA's premium leather chukka is sturdy enough to hold up to rugged work conditions, yet comfortable enough for long hours on your feet *Premium leather upper *CUSH-N-CREPE Forward Glide® tapered sole is designed to enhance your natural... more

$114.95

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ShoeMall.com

(50,000+)
Justin Boots Justin Men's Casual Moc Toe Chukka Boots, 9.5d, Dark Brown

Justin Boots Justin Men's Casual Moc Toe Chukka Boots, 9.5d, Dark Brown

Kick back and relax in these Waxy Dark Brown Driver Moc Chukka Boots. Crafted with care and made for comfort, the rugged leather gives them a lived-in look. The leather laces are durable to everyday wear and tear and the traditional moccasin toe... more

$79.99

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Spring Step Men Mathias Chukka Boots - Black Black

Spring Step Men Mathias Chukka Boots - Black Black

The Spring Step Mens Mathias ankle boots showcase a leather lace up chukka boot style with contrasting leather, a rounded toe, and leather heel piece detail. They feature metal eyelets, durable cotton waxed laces, soft textile lining, a removable... more

$99.99

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Boscov's

(50,000+)
Men's Timberland Davis Square Leather Boots, Grey, Size 10.5

Men's Timberland Davis Square Leather Boots, Grey, Size 10.5

Shoes by Timberland. Comes in Dark Grey, Size 10. 5 M. Leather and canvas chukkas, by the brand first known for their iconic wheat-colored boots. Upper features leather sourced by an environmentally progressive tannery along with the nearly... more

$87.99

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Blair.com

(475,000+)
Men's Timberland Davis Square Leather Boots, Tan, Size 9

Men's Timberland Davis Square Leather Boots, Tan, Size 9

Shoes by Timberland. Comes in Wheat, Size 9 M. Leather and canvas chukkas, by the brand first known for their iconic wheat-colored boots. Upper features leather sourced by an environmentally progressive tannery along with the nearly indestructible... more

$87.99

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Blair.com

(475,000+)
Men's Timberland Davis Square Leather Boots, Tan, Size 13

Men's Timberland Davis Square Leather Boots, Tan, Size 13

Shoes by Timberland. Comes in Wheat, Size 13 M. Leather and canvas chukkas, by the brand first known for their iconic wheat-colored boots. Upper features leather sourced by an environmentally progressive tannery along with the nearly indestructible... more

$87.99

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Blair.com

(475,000+)
Georgia Boot Men’s Leather 5" Chukka Wedge Work Boot Wide Width Available - Brown, Size: 10.5, Barracuda Gold

Georgia Boot Men’s Leather 5" Chukka Wedge Work Boot Wide Width Available - Brown, Size: 10.5, Barracuda Gold

Cleaning out the stalls, hauling hay and distributing food to livestock is extremely hard work. To help you accomplish the daily tasks on the farm, you should consider wearing these Georgia Farm & Ranch Chukka Work Boots. These Chukka boots have been... more

$144.00 $124.99

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Georgia Boot Men’s Leather 5" Chukka Wedge Work Boot Wide Width Available - Brown, Size: 12, Barracuda Gold

Georgia Boot Men’s Leather 5" Chukka Wedge Work Boot Wide Width Available - Brown, Size: 12, Barracuda Gold

Cleaning out the stalls, hauling hay and distributing food to livestock is extremely hard work. To help you accomplish the daily tasks on the farm, you should consider wearing these Georgia Farm & Ranch Chukka Work Boots. These Chukka boots have been... more

$144.00 $124.99

FREE shipping

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Georgia Boot Men’s Leather 5" Chukka Wedge Work Boot Wide Width Available - Brown, Size: 7.5, Barracuda Gold

Georgia Boot Men’s Leather 5" Chukka Wedge Work Boot Wide Width Available - Brown, Size: 7.5, Barracuda Gold

Cleaning out the stalls, hauling hay and distributing food to livestock is extremely hard work. To help you accomplish the daily tasks on the farm, you should consider wearing these Georgia Farm & Ranch Chukka Work Boots. These Chukka boots have been... more

$144.00 $124.99

FREE shipping

go to store
Trask Men's Brady Chukka Boot, Bourbon, 8 M US

Trask Men's Brady Chukka Boot, Bourbon, 8 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$239.99

FREE shipping

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Trask Men's Brady Chukka Boot, Bourbon, 10.5 M US

Trask Men's Brady Chukka Boot, Bourbon, 10.5 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$239.99

FREE shipping

go to store
Trask Men's Brady Chukka Boot, Bourbon, 11 M US

Trask Men's Brady Chukka Boot, Bourbon, 11 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$239.99

FREE shipping

go to store
Trask Men's Brady Chukka Boot, Saddle Tan, 8 M US

Trask Men's Brady Chukka Boot, Saddle Tan, 8 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$223.34

FREE shipping

go to store
Trask Men's Brady Chukka Boot, Bourbon, 11.5 M US

Trask Men's Brady Chukka Boot, Bourbon, 11.5 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$239.99

FREE shipping

go to store
Trask Men's Brady Chukka Boot, Saddle Tan, 12 M US

Trask Men's Brady Chukka Boot, Saddle Tan, 12 M US

A softer take on an iconic style, crafted of hand-selected premium leathers, including horween oiled american steer with a rugged character that gains richness with wear, horween chromexcel american bison, norwegian elk, italian suede that’s waxed and... more

$200.00

FREE shipping

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