You're in Men's Shoes

Need a Personal Shopper?

Subscribe to
Bizrate emails for the hottest
deals & products
,
PLUS a chance to

WIN $25

sign me up!

New winners chosen weekly.
No purchase necessary.

Timberland Men's Baluster Chukka Shoe

Timberland Men's Baluster Chukka Shoe

Sturdy, yet stylish, these plain toe chukka shoes go from the office to the outdoors with ease. From Timberland.

at QVC

Men's Timberland Earthkeepers  Britton Hill Chukka - Dark Brown Smooth Boots

Men's Timberland Earthkeepers Britton Hill Chukka - Dark Brown Smooth Boots

Premium uppers from an LWG Silver-rated tannery provides durability. The TPR welt gives this shoe a premium look. Comes with 100% organic cotton laces. The shoe's removable anti-fatigue footbed provides all-day comfort and support. The footbed features... ... more

Men's Timberland Earthkeepers Britton Hill Chukka - Dark Brown Smooth Boots

Premium uppers from an LWG Silver-rated tannery provides durability. The TPR welt gives this shoe a premium look. Comes with 100% organic cotton laces. The shoe's removable anti-fatigue footbed provides all-day comfort and support. The footbed features...

(150,000+)

$169.95

FREE shipping

go to store
(150,000+)
Timberland Earthkeepers Brook Park Chukka Men's Lace-up Boots

Timberland Earthkeepers Brook Park Chukka Men's Lace-up Boots

Free Shipping Both Ways! Keep it easy and classy in the Earthkeepers Brook Park Chukka from Timberland. Full grain leather upper. Lace-up closure for an adjustable and secure fit. 100% recycled PET herringbone lining provides comfort and breathability.... ... more

Timberland Earthkeepers Brook Park Chukka Men's Lace-up Boots

Free Shipping Both Ways! Keep it easy and classy in the Earthkeepers Brook Park Chukka from Timberland. Full grain leather upper. Lace-up closure for an adjustable and secure fit. 100% recycled PET herringbone lining provides comfort and breathability....

Zappos.com

(300,000+)

$130.00

FREE shipping

go to store

Zappos.com

(300,000+)
Timberland Earthkeepers Britton Hill Chukka Men's Lace-up Boots

Timberland Earthkeepers Britton Hill Chukka Men's Lace-up Boots

Free Shipping Both Ways! Wow your friend with fresh style in the Earthkeepers Britton Hill Chukka from Timberland. Premium full grain leather upper with perforations and contrast stitching details. Lace-up closure for an adjustable fit. TPR welt for an... ... more

Timberland Earthkeepers Britton Hill Chukka Men's Lace-up Boots

Free Shipping Both Ways! Wow your friend with fresh style in the Earthkeepers Britton Hill Chukka from Timberland. Premium full grain leather upper with perforations and contrast stitching details. Lace-up closure for an adjustable fit. TPR welt for an...

Zappos.com

(300,000+)

$170.00

FREE shipping

go to store

Zappos.com

(300,000+)
Timberland Men's Baluster Chukka

Timberland Men's Baluster Chukka

The Timberland 54568 boots feature a leather upper with a moc toe. The man-made outsole lends lasting traction and wear. ... more

Timberland Men's Baluster Chukka

The Timberland 54568 boots feature a leather upper with a moc toe. The man-made outsole lends lasting traction and wear.

Amazon.com

$71.87

FREE shipping

go to store
Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 11.5M Men's Shoes

Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 11.5M Men's Shoes

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in simple styling, slip-on a pair with the denim of your choice. ... more

Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 11.5M Men's Shoes

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in simple styling, slip-on a pair with the denim of your choice.

Sperry Top-Sider

(5,000+)

$130.00 $99.99

go to store
Sperry Top-Sider Gold Cup Bellingham ASV Chukka Boot Tan, Size 11.5M Men's Shoes

Sperry Top-Sider Gold Cup Bellingham ASV Chukka Boot Tan, Size 11.5M Men's Shoes

The Gold Cup Collection features premium hand-sewn leather uppers and luxurious Lambskin linings. Seasonal style updates include hand-burnished leathers, soft suedes and unique color combinations. In addition to their fine workmanship, Bellingham Chukka B ... more

Sperry Top-Sider Gold Cup Bellingham ASV Chukka Boot Tan, Size 11.5M Men's Shoes

The Gold Cup Collection features premium hand-sewn leather uppers and luxurious Lambskin linings. Seasonal style updates include hand-burnished leathers, soft suedes and unique color combinations. In addition to their fine workmanship, Bellingham Chukka B

Sperry Top-Sider

(5,000+)

$195.00 $139.99

FREE shipping

go to store
Crocs Navy / Clay Men's Beach Line Boat Chukka Shoes

Crocs Navy / Clay Men's Beach Line Boat Chukka Shoes

Navy / Clay Crocs Men's Beach Line Boat Chukka. Available in size M7,M8,M9,M10,M11,M12,M13 ... more

Crocs Navy / Clay Men's Beach Line Boat Chukka Shoes

Navy / Clay Crocs Men's Beach Line Boat Chukka. Available in size M7,M8,M9,M10,M11,M12,M13

(1,000+)

$79.99

FREE shipping

go to store
(1,000+)
Men's Stitch Out Chukkas

Men's Stitch Out Chukkas

Enjoy everyday comfort with these handsome chukkas. Perfect for casual wear and walks in the outdoors. The handsewn upper is made with a very soft and supple suede that has a natural look and texture. A solid stitch-out construction makes these shoes... ... more

Men's Stitch Out Chukkas

Enjoy everyday comfort with these handsome chukkas. Perfect for casual wear and walks in the outdoors. The handsewn upper is made with a very soft and supple suede that has a natural look and texture. A solid stitch-out construction makes these shoes...

(2,500+)

$99.00 $49.99

FREE shipping

go to store
(2,500+)
Men's Timberland PRO Powertrain Alloy Safety Toe ESD - Black/Grey Microfiber Lace Up Shoes

Men's Timberland PRO Powertrain Alloy Safety Toe ESD - Black/Grey Microfiber Lace Up Shoes

A rugged, breathable upper combines with an alloy safety toe for lightweight protection in the Powertrain. Cement construction allows for flexibility and a reduced break-in time, and a mesh lining is treated to prevent odors. A conductive midsole gives... ... more

Men's Timberland PRO Powertrain Alloy Safety Toe ESD - Black/Grey Microfiber Lace Up Shoes

A rugged, breathable upper combines with an alloy safety toe for lightweight protection in the Powertrain. Cement construction allows for flexibility and a reduced break-in time, and a mesh lining is treated to prevent odors. A conductive midsole gives...

(150,000+)

$119.95

FREE shipping

go to store
(150,000+)
Timberland Earthkeepers Stormbuck Duck Chukka Men's Lace up casual Shoes

Timberland Earthkeepers Stormbuck Duck Chukka Men's Lace up casual Shoes

Free Shipping on all orders! Take on the unpredictable weather by storm in the stylish Earthkeepers Stormbuck Duck Chukka from Timberland. Waterproof, full grain leather upper provides all-day protection for any type of weather. Molded TPU brogue toe... ... more

Timberland Earthkeepers Stormbuck Duck Chukka Men's Lace up casual Shoes

Free Shipping on all orders! Take on the unpredictable weather by storm in the stylish Earthkeepers Stormbuck Duck Chukka from Timberland. Waterproof, full grain leather upper provides all-day protection for any type of weather. Molded TPU brogue toe...

6pm.com

$140.00 $77.99

FREE shipping

go to store
Men's Lakeside Boat Shoes, Chukka 9.5 M(D) Brown

Men's Lakeside Boat Shoes, Chukka 9.5 M(D) Brown

Here in Maine, you don't have to walk very far to go from city sidewalk to shoreside dock. With this in mind, we redesigned our classic boat shoe style to provide even more comfort and stability on life's ever-changing terrain. Full-grain, waterproof... ... more

Men's Lakeside Boat Shoes, Chukka 9.5 M(D) Brown

Here in Maine, you don't have to walk very far to go from city sidewalk to shoreside dock. With this in mind, we redesigned our classic boat shoe style to provide even more comfort and stability on life's ever-changing terrain. Full-grain, waterproof...

(2,500+)

$89.00 $79.99

FREE shipping

go to store
(2,500+)
Timberland Men's Groveton Leather and Fabric Chukka Blackout Nubuck-Textile-White Shoes, Size 11 M - 6746A

Timberland Men's Groveton Leather and Fabric Chukka Blackout Nubuck-Textile-White Shoes, Size 11 M - 6746A

Timberland Men's Groveton Leather and Fabric Chukka Blackout Nubuck-Textile-White Shoes - 6746A ... more

Timberland Men's Groveton Leather and Fabric Chukka Blackout Nubuck-Textile-White Shoes, Size 11 M - 6746A

Timberland Men's Groveton Leather and Fabric Chukka Blackout Nubuck-Textile-White Shoes - 6746A

TheShoeMart

(5,000+)

$69.95

FREE shipping

go to store

TheShoeMart

(5,000+)
Timberland Earthkeepers Richmont Moc Toe Chukka Men's Shoes

Timberland Earthkeepers Richmont Moc Toe Chukka Men's Shoes

Free Shipping on all orders! Whether you're taking a stroll through the park or hiking it to work, your feet will be in full comfort the entire ride. Burnished full grain leather upper with contrast stitching for added appeal. Leather is from a tannery... ... more

Timberland Earthkeepers Richmont Moc Toe Chukka Men's Shoes

Free Shipping on all orders! Whether you're taking a stroll through the park or hiking it to work, your feet will be in full comfort the entire ride. Burnished full grain leather upper with contrast stitching for added appeal. Leather is from a tannery...

6pm.com

$100.00 $69.99

FREE shipping

go to store
Timberland Men's Earthkeepers Richmont Moc Toe Chukka Dark Brown Oiled Shoes, Size 16 M - 5043A

Timberland Men's Earthkeepers Richmont Moc Toe Chukka Dark Brown Oiled Shoes, Size 16 M - 5043A

Timberland Men's Earthkeepers Richmont Moc Toe Chukka Dark Brown Oiled Shoes - 5043A ... more

Timberland Men's Earthkeepers Richmont Moc Toe Chukka Dark Brown Oiled Shoes, Size 16 M - 5043A

Timberland Men's Earthkeepers Richmont Moc Toe Chukka Dark Brown Oiled Shoes - 5043A

TheShoeMart

(5,000+)

$99.95

FREE shipping

go to store

TheShoeMart

(5,000+)
Men's Merona Eric Chukka Boots - Assorted Colors

Men's Merona Eric Chukka Boots - Assorted Colors

Free Shipping On Orders $50+

Find boots at Target.com! Men's merona eric chukka boots - assorted colors ... more

Men's Merona Eric Chukka Boots - Assorted Colors

Find boots at Target.com! Men's merona eric chukka boots - assorted colors

$44.99

go to store
Timberland Men's EK Stormbuck Duck Chukka Rain Shoe

Timberland Men's EK Stormbuck Duck Chukka Rain Shoe

Modern and rugged, with a big dollop of style, the Timberland EK Stormbuck Duck Chukka boot is quite a catch. Featuring premium full-grain waterproof leather upper, a waterproof seam-sealed construction, and a molded TPU brogue detailed toe cap for... ... more

Timberland Men's EK Stormbuck Duck Chukka Rain Shoe

Modern and rugged, with a big dollop of style, the Timberland EK Stormbuck Duck Chukka boot is quite a catch. Featuring premium full-grain waterproof leather upper, a waterproof seam-sealed construction, and a molded TPU brogue detailed toe cap for...

Amazon Marketplace

$100.33

FREE shipping

go to store
Vans Chukka Low - Mens - Navy/Gum

Vans Chukka Low - Mens - Navy/Gum

The Vans Chukka Low was designed by the Vans skate team, and features styles customized by Chima Ferguson, Keegan Sauder and Chris Pfanner. This skate shoe is based on other classics like the Vans Authentic and the Vans Chukka Boot, and spotlights the... ... more

Vans Chukka Low - Mens - Navy/Gum

The Vans Chukka Low was designed by the Vans skate team, and features styles customized by Chima Ferguson, Keegan Sauder and Chris Pfanner. This skate shoe is based on other classics like the Vans Authentic and the Vans Chukka Boot, and spotlights the...

Eastbay

(900,000+)

$64.99

go to store

Eastbay

(900,000+)
Bates Men's Lites E00078 Chukka Work Shoe

Bates Men's Lites E00078 Chukka Work Shoe

Bates Lites Leather Padded Collar Chukkas ... comfort from the ground up! Lace up these Chukkas for unbeatable comfort! A foot-pampering, fully-removable footbed with breathable lining is extremely comfortable for your long stints on your feet. The... ... more

Bates Men's Lites E00078 Chukka Work Shoe

Bates Lites Leather Padded Collar Chukkas ... comfort from the ground up! Lace up these Chukkas for unbeatable comfort! A foot-pampering, fully-removable footbed with breathable lining is extremely comfortable for your long stints on your feet. The...

Amazon.com

$39.99

go to store
Men's Black Label by L.B. Evans Langley Chukka Boots - Grey 10.5

Men's Black Label by L.B. Evans Langley Chukka Boots - Grey 10.5

Free Shipping On Orders $50+

Find boots at Target.com! Men's black label by l.b. Evans langley chukka boots - grey 10.5 ... more

Men's Black Label by L.B. Evans Langley Chukka Boots - Grey 10.5

Find boots at Target.com! Men's black label by l.b. Evans langley chukka boots - grey 10.5

$59.99

FREE shipping

go to store
Timberland Men's EK City Lite Chukka Boot,Brown Oiled,8 M US

Timberland Men's EK City Lite Chukka Boot,Brown Oiled,8 M US

Give a boost to your confidence in the smart Timberland Earthkeepers City Lite Chukka outdoor boot; it is on-trend for casual outings on the town. The upper of this mens lace-up boot utilizes superior quality burnished full-grain leather for toughness... ... more

Timberland Men's EK City Lite Chukka Boot,Brown Oiled,8 M US

Give a boost to your confidence in the smart Timberland Earthkeepers City Lite Chukka outdoor boot; it is on-trend for casual outings on the town. The upper of this mens lace-up boot utilizes superior quality burnished full-grain leather for toughness...

Amazon.com

$89.96

FREE shipping

go to store
Timberland Mens Hudston Brogue Chukka Casual Shoes

Timberland Mens Hudston Brogue Chukka Casual Shoes

Show off your fashion-savvy style with the new Timberland Earthkeepers Hudston Brogue Chukka boot. Great for everyday wear, this versatile and stylish lace-up is accented with punch-out detailing for added appeal. Featuring a premium full-grain and... ... more

Timberland Mens Hudston Brogue Chukka Casual Shoes

Show off your fashion-savvy style with the new Timberland Earthkeepers Hudston Brogue Chukka boot. Great for everyday wear, this versatile and stylish lace-up is accented with punch-out detailing for added appeal. Featuring a premium full-grain and...

Amazon Marketplace

$87.88

FREE shipping

go to store
Florsheim Vantage Chukka Boots - Leather (For Men) ? BROWN TUMBLED

Florsheim Vantage Chukka Boots - Leather (For Men) ? BROWN TUMBLED

Get 30% off $100 or more with PCZILLAUS5

CLOSEOUTS . Men who prefer boots to shoes in casual and dress venues will embrace the comfort and polished good looks of Florsheim's Vantage chukka boots. Not only is the top line softly padded, but the Comfortechnology interior absorbs shock, supports... ... more

Florsheim Vantage Chukka Boots - Leather (For Men) ? BROWN TUMBLED

CLOSEOUTS . Men who prefer boots to shoes in casual and dress venues will embrace the comfort and polished good looks of Florsheim's Vantage chukka boots. Not only is the top line softly padded, but the Comfortechnology interior absorbs shock, supports...

(700,000+)

$135.00 $94.95

go to store
(700,000+)
Timberland Men's EK Brook Park Zip Chukka Boot,Red/Brown Smooth,7.5 M US

Timberland Men's EK Brook Park Zip Chukka Boot,Red/Brown Smooth,7.5 M US

A boot with character, the all-new Timberland EK Brook Park Zip Boot is sure to make a statement everywhere you go. Great for everyday use, this handsome boot is naturally lightweight, flexible and durable. Boasting of a premium full-grain leather... ... more

Timberland Men's EK Brook Park Zip Chukka Boot,Red/Brown Smooth,7.5 M US

A boot with character, the all-new Timberland EK Brook Park Zip Boot is sure to make a statement everywhere you go. Great for everyday use, this handsome boot is naturally lightweight, flexible and durable. Boasting of a premium full-grain leather...

Amazon.com

$150.00

FREE shipping

go to store
Timberland PRO Men's Mudsill Steel Toe Work Oxford - Black 7.5;8;8.5;9;9.5;10;10.5;11;12;13

Timberland PRO Men's Mudsill Steel Toe Work Oxford - Black 7.5;8;8.5;9;9.5;10;10.5;11;12;13

Get the rugged durability and protection you need from the men's Timberland PRO Mudsill work shoe. Though it's styled like a sneaker, this heavy-duty shoe features a steel toe with protective toe cap, OrthoLite footbed and antimicrobial lining. The... ... more

Timberland PRO Men's Mudsill Steel Toe Work Oxford - Black 7.5;8;8.5;9;9.5;10;10.5;11;12;13

Get the rugged durability and protection you need from the men's Timberland PRO Mudsill work shoe. Though it's styled like a sneaker, this heavy-duty shoe features a steel toe with protective toe cap, OrthoLite footbed and antimicrobial lining. The...

Sears.com

(10,000+)

$115.00 $92.00

FREE shipping

go to store

Sears.com

(10,000+)
Frye Mens Carter Chukka Shoes

Frye Mens Carter Chukka Shoes

A classic chukka made with a crepe bottom. This chukka is made in leather that is tumbled for a soft, pebbled look.Soft pebbled full grain leather upper. Unlined. Crepe outsole. Size and Fit3 3/4" shaft height. 1" heel. Measurements based on size 9. ... more

Frye Mens Carter Chukka Shoes

A classic chukka made with a crepe bottom. This chukka is made in leather that is tumbled for a soft, pebbled look.Soft pebbled full grain leather upper. Unlined. Crepe outsole. Size and Fit3 3/4" shaft height. 1" heel. Measurements based on size 9.

Sheplers

$257.99

FREE shipping

go to store
J. Shoes Volunteer Chukka Boots (For Men) ? BLACK

J. Shoes Volunteer Chukka Boots (For Men) ? BLACK

Get 30% off $100 or more with PCZILLAUS5

CLOSEOUTS . Elevate your look with J. Shoes Volunteer chukka boots, a round toe leather lace-up for those hours spent off the clock. Available Colors: MEDIUM BROWN, BLACK, MEDIUM BROWN/CLOVE. Sizes: 9, 9.5, 10, 10.5, 11, 11.5, 12, 13. ... more

J. Shoes Volunteer Chukka Boots (For Men) ? BLACK

CLOSEOUTS . Elevate your look with J. Shoes Volunteer chukka boots, a round toe leather lace-up for those hours spent off the clock. Available Colors: MEDIUM BROWN, BLACK, MEDIUM BROWN/CLOVE. Sizes: 9, 9.5, 10, 10.5, 11, 11.5, 12, 13.

(700,000+)

$161.00 $69.95

go to store
(700,000+)
Clarks Feather-Weight Chukkas Brown 8 1/2

Clarks Feather-Weight Chukkas Brown 8 1/2

Weighing less than 12 oz. each, these wear-anywhere Clarks shoes are 50% lighter than standard chukkas, so they add almost nothing to your luggage while enhancing your travel wardrobe. Crafted of durable pebbled leather, they pair easily with jeans,... ... more

Clarks Feather-Weight Chukkas Brown 8 1/2

Weighing less than 12 oz. each, these wear-anywhere Clarks shoes are 50% lighter than standard chukkas, so they add almost nothing to your luggage while enhancing your travel wardrobe. Crafted of durable pebbled leather, they pair easily with jeans,...

TravelSmith

$120.00 $84.00

go to store
Dexter, Dexter Comfort, Mens Benton Boat Shoe, Mens, Casual, Boat Shoes, Boat

Dexter, Dexter Comfort, Mens Benton Boat Shoe, Mens, Casual, Boat Shoes, Boat

Whether on land or on a boat, the Benton is sure to please! It features a faux suede upper with traditional boat shoe details, laces for good fit, mesh lining, cushiony memory foam insole for all-day comfort, and a lightweight outsole. Manmade materials. ... more

Dexter, Dexter Comfort, Mens Benton Boat Shoe, Mens, Casual, Boat Shoes, Boat

Whether on land or on a boat, the Benton is sure to please! It features a faux suede upper with traditional boat shoe details, laces for good fit, mesh lining, cushiony memory foam insole for all-day comfort, and a lightweight outsole. Manmade materials.

Payless.com

$39.99

go to store
Men's Timberland Earthkeepers 'Hudston' Suede Chukka Boot

Men's Timberland Earthkeepers 'Hudston' Suede Chukka Boot

Featuring a vulcanized construction, a modern zip chukka boot crafted from soft, supple suede is fronted with a classic moc toe. In keeping with Timberland Earthkeepers' eco-conscious philosophy, recycled materials have been incorporated in the... ... more

Men's Timberland Earthkeepers 'Hudston' Suede Chukka Boot

Featuring a vulcanized construction, a modern zip chukka boot crafted from soft, supple suede is fronted with a classic moc toe. In keeping with Timberland Earthkeepers' eco-conscious philosophy, recycled materials have been incorporated in the...

Nordstrom

(1,000+)

$99.95 $69.96

FREE shipping

go to store

Nordstrom

(1,000+)
Men's Timberland 'Abington - Booth Bay' Chukka Boot

Men's Timberland 'Abington - Booth Bay' Chukka Boot

Heritage-steeped design pervades in a premium chukka boot crafted in panels of leather and suede and set on a sturdy Vibram rubber sole. Color(s): black quartz/ black suede, chestnut quartz/ brown suede. Brand: Timberland. Style Name: Timberland... ... more

Men's Timberland 'Abington - Booth Bay' Chukka Boot

Heritage-steeped design pervades in a premium chukka boot crafted in panels of leather and suede and set on a sturdy Vibram rubber sole. Color(s): black quartz/ black suede, chestnut quartz/ brown suede. Brand: Timberland. Style Name: Timberland...

Nordstrom

(1,000+)

$180.00

FREE shipping

go to store

Nordstrom

(1,000+)
Crocs Black / Black Men's Yukon Slip-On Shoe Shoes

Crocs Black / Black Men's Yukon Slip-On Shoe Shoes

Black / Black Crocs Men's Yukon Slip-on Shoe. Available in size M7,M8,M9,M10,M11,M12,M13 ... more

Crocs Black / Black Men's Yukon Slip-On Shoe Shoes

Black / Black Crocs Men's Yukon Slip-on Shoe. Available in size M7,M8,M9,M10,M11,M12,M13

(1,000+)

$64.99 $39.99

FREE shipping

go to store
(1,000+)
Vans Chukka Low Navy/Gum Canvas) Men's Skate Shoes

Vans Chukka Low Navy/Gum Canvas) Men's Skate Shoes

Free Shipping Both Ways! Designed by the Vans skate team, the Chukka Low blends the classic skate style of the Authentic with the timeless style of the chukka boot. Each season, Vans will introduce a different rider's personal colorway to help showcase... ... more

Vans Chukka Low Navy/Gum Canvas) Men's Skate Shoes

Free Shipping Both Ways! Designed by the Vans skate team, the Chukka Low blends the classic skate style of the Authentic with the timeless style of the chukka boot. Each season, Vans will introduce a different rider's personal colorway to help showcase...

Zappos.com

(300,000+)

$65.00

FREE shipping

go to store

Zappos.com

(300,000+)
Timberland Earthkeepers City Lite Waterproof Chukka Men's Shoes

Timberland Earthkeepers City Lite Waterproof Chukka Men's Shoes

Free Shipping Both Ways! Get the rugged, yet refined look you're aiming for with the Timberland® Earthkeepers® City Lite Waterproof Chukka boot. Waterproof, oiled or smooth leather upper with handsewn stitching details for an authentic style. Lace... ... more

Timberland Earthkeepers City Lite Waterproof Chukka Men's Shoes

Free Shipping Both Ways! Get the rugged, yet refined look you're aiming for with the Timberland® Earthkeepers® City Lite Waterproof Chukka boot. Waterproof, oiled or smooth leather upper with handsewn stitching details for an authentic style. Lace...

Zappos.com

(300,000+)

$120.00

FREE shipping

go to store

Zappos.com

(300,000+)
Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 13M Men's Shoes

Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 13M Men's Shoes

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in simple styling, slip-on a pair with the denim of your choice. ... more

Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 13M Men's Shoes

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in simple styling, slip-on a pair with the denim of your choice.

Sperry Top-Sider

(5,000+)

$130.00 $99.99

go to store
Rockport RocSports Lite 2 Chukka Men's Shoes

Rockport RocSports Lite 2 Chukka Men's Shoes

Free Shipping Both Ways! Walking on air and looking like a million bucks may sound cliché, but you'll be doing both with a smile in this sporty boot. Soft leather upper in a casual chukka boot style with contrasting laces and midsole. Classic lace-up... ... more

Rockport RocSports Lite 2 Chukka Men's Shoes

Free Shipping Both Ways! Walking on air and looking like a million bucks may sound cliché, but you'll be doing both with a smile in this sporty boot. Soft leather upper in a casual chukka boot style with contrasting laces and midsole. Classic lace-up...

Zappos.com

(300,000+)

$120.00

FREE shipping

go to store

Zappos.com

(300,000+)
Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 10.5M Men's Shoes

Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 10.5M Men's Shoes

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in simple styling, slip-on a pair with the denim of your choice. ... more

Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 10.5M Men's Shoes

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in simple styling, slip-on a pair with the denim of your choice.

Sperry Top-Sider

(5,000+)

$130.00 $99.99

go to store
Sperry Top-Sider Bushwick Chukka Boot Tan, Size 10M Men's Shoes

Sperry Top-Sider Bushwick Chukka Boot Tan, Size 10M Men's Shoes

$200.00

FREE shipping

go to store
Sperry Top-Sider Authentic Original Cyclone Chukka Boot Earth, Size 13M Men's Shoes

Sperry Top-Sider Authentic Original Cyclone Chukka Boot Earth, Size 13M Men's Shoes

$110.00

FREE shipping

go to store
SKECHERS Superior Relaxed Fit Chukka Men's Shoes

SKECHERS Superior Relaxed Fit Chukka Men's Shoes

Free Shipping Both Ways! Conquer the outdoors in style with the SKECHERS Superior Relaxed Fit Chukka. Leather upper with contrast stitching. Pull tab at heel. Lace up front with blind eyelets. Plain toe. S logo at heel. Textile lining and insole.... ... more

SKECHERS Superior Relaxed Fit Chukka Men's Shoes

Free Shipping Both Ways! Conquer the outdoors in style with the SKECHERS Superior Relaxed Fit Chukka. Leather upper with contrast stitching. Pull tab at heel. Lace up front with blind eyelets. Plain toe. S logo at heel. Textile lining and insole....

Zappos.com

(300,000+)

$79.95

FREE shipping

go to store

Zappos.com

(300,000+)
Original Penguin Chukka Men's Lace up casual Shoes

Original Penguin Chukka Men's Lace up casual Shoes

Free Shipping Both Ways! Channel vintage appeal in the good looks of Original Penguin. Smooth leather upper with tonal stitching. Contrast heel counter. Lace up front closure with blind eyelets. Chukka boot silhouette. Man-made lining and insole.... ... more

Original Penguin Chukka Men's Lace up casual Shoes

Free Shipping Both Ways! Channel vintage appeal in the good looks of Original Penguin. Smooth leather upper with tonal stitching. Contrast heel counter. Lace up front closure with blind eyelets. Chukka boot silhouette. Man-made lining and insole....

Zappos.com

(300,000+)

$180.00

FREE shipping

go to store

Zappos.com

(300,000+)
Show
Hide
Hide