Best Seller
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

$265.00

FREE shipping

go to store
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

$265.00

FREE shipping

go to store
Best Seller
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

$265.00

FREE shipping

go to store
Frye Jones Chukka (Taupe Soft Italian Nubuck) Men's Boots

Frye Jones Chukka (Taupe Soft Italian Nubuck) Men's Boots

The casually refined Frye Jones Chukka easily complements your relaxed weekend style. Well-crafted oiled suede or vintage veg tan leather upper. Leather type stated in color name. Traditional lace-up with waxed laces. Goodyear welt construction for... more

$328.00 $164.00

go to store
Johnston & Murphy Conard Casual Dress Cap Toe Chukka (Mahogany Italian Calfskin) Men's Boots

Johnston & Murphy Conard Casual Dress Cap Toe Chukka (Mahogany Italian Calfskin) Men's Boots

Complete your wardrobe with the handsome appeal of the Johnston Murphy Conard Casual Dress Cap Toe Chukka! Hand-burnished Italian leather. Stitch-and-turn seaming for a clean look with no visible stitching. Leather lining offers a soft feel. Cement... more

$178.95 $70.99

go to store
Frye Jones Chukka (Taupe Soft Italian Nubuck) Men's Boots

Frye Jones Chukka (Taupe Soft Italian Nubuck) Men's Boots

The casually refined Frye Jones Chukka easily complements your relaxed weekend style. Well-crafted oiled suede or vintage veg tan leather upper. Leather type stated in color name. Traditional lace-up with waxed laces. Goodyear welt construction for... more

$328.00 $164.00

go to store
Frye Will Chukka (Black Pressed Full Grain) Men's Boots

Frye Will Chukka (Black Pressed Full Grain) Men's Boots

The Frye Will Chukka offers a clean relaxed style that will match perfectly with casual Fridays and weekend events. Pressed full grain Italian leather or oiled Italian suede upper. Leather type stated in color name. Features Goodyear welt craftsmanship... more

$328.00

go to store

Zappos.com

(425,000+)
Frye Will Chukka (Copper Pressed Full Grain) Men's Boots

Frye Will Chukka (Copper Pressed Full Grain) Men's Boots

The Frye Will Chukka offers a clean relaxed style that will match perfectly with casual Fridays and weekend events. Pressed full grain Italian leather or oiled Italian suede upper. Leather type stated in color name. Features Goodyear welt craftsmanship... more

$328.00

go to store

Zappos.com

(425,000+)
Frye Will Chukka (Black Pressed Full Grain) Men's Boots

Frye Will Chukka (Black Pressed Full Grain) Men's Boots

The Frye Will Chukka offers a clean relaxed style that will match perfectly with casual Fridays and weekend events. Pressed full grain Italian leather or oiled Italian suede upper. Leather type stated in color name. Features Goodyear welt craftsmanship... more

$328.00

go to store

Zappos.com

(425,000+)
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

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

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

Free Shipping on All Products

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

FREE shipping

go to store

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

Free Shipping on All Products

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

FREE shipping

go to store

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

go to store
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 $175.00

FREE shipping

go to store
Men's Florsheim Jet Chukka - Black Smooth Leather Boots

Men's Florsheim Jet Chukka - Black Smooth Leather Boots

Free Shipping on All Products

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

FREE shipping

go to store

shoes.com

(175,000+)
Joseph Abboud Oslow Leather Chukka Boots CLEARANCE Men's Shoes

Joseph Abboud Oslow Leather Chukka Boots CLEARANCE Men's Shoes

This classic casual wear favorite is refined with a smooth polished leather upper and fine stitching throughout. EVA sole with reversed cleat forefoot. Wood stack heel. Leather welt and lining. Lightweight. Hand finished Italian leather upper. Spot... more

$145.00 $74.98

FREE shipping

go to store
Joseph Abboud Oslow Leather Chukka Boots CLEARANCE Men's Shoes

Joseph Abboud Oslow Leather Chukka Boots CLEARANCE Men's Shoes

This classic casual wear favorite is refined with a smooth polished leather upper and fine stitching throughout. EVA sole with reversed cleat forefoot. Wood stack heel. Leather welt and lining. Lightweight. Hand finished Italian leather upper. Spot... more

$145.00 $74.98

FREE shipping

go to store
Joseph Abboud Oslow Leather Chukka Boots CLEARANCE Men's Shoes

Joseph Abboud Oslow Leather Chukka Boots CLEARANCE Men's Shoes

This classic casual wear favorite is refined with a smooth polished leather upper and fine stitching throughout. EVA sole with reversed cleat forefoot. Wood stack heel. Leather welt and lining. Lightweight. Hand finished Italian leather upper. Spot... more

$145.00 $74.98

FREE shipping

go to store
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

FREE shipping

go to store
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

FREE shipping

go to store
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

go to store
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

go to store
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

go to store
Benton Welt Chukka Boot - Wide Width Available

Benton Welt Chukka Boot - Wide Width Available

Sizing: True to size. M=standard width W=wide width. Round toe. Contrasting suede and leather construction. Topstitching. Lace-up. Lightly padded insole. Approx. 4.5" shaft height. Imported more

$250.00 $129.97

go to store
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

FREE shipping

go to store
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

FREE shipping

go to store
Benton Welt Chukka Boot - Wide Width Available

Benton Welt Chukka Boot - Wide Width Available

Sizing: True to size. M=standard width W=wide width. Round toe. Contrasting suede and leather construction. Topstitching. Lace-up. Lightly padded insole. Approx. 4.5" shaft height. Imported more

$250.00 $129.97

go to store
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 $15.99

go to store
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

FREE shipping

go to store

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

FREE shipping

go to store

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

go to store
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

go to store

Boscov's

(50,000+)
Benton Welt Chukka Boot - Wide Width Available

Benton Welt Chukka Boot - Wide Width Available

Sizing: True to size. M=standard width W=wide width. Round toe. Contrasting suede and leather construction. Topstitching. Lace-up. Lightly padded insole. Approx. 4.5" shaft height. Imported more

$250.00 $129.97

go to store
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

go to store

Blair.com

(475,000+)
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

go to store

Blair.com

(475,000+)
Men's Timberland Davis Square Leather Boots, Tan, Size 8.5

Men's Timberland Davis Square Leather Boots, Tan, Size 8.5

Shoes by Timberland. Comes in Wheat, Size 8. 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 indestructible... more

$87.99

go to store

Blair.com

(475,000+)
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

$265.00

FREE shipping

go to store
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

$265.00

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

$265.00

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

$265.00

FREE shipping

go to store

More information about Men's Shoes

Best prices on Italian leather chukka boot 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.