The sleek and handsome Branning Chukka Boot features cement waterproof construction for durability and a memory foam cushioned footbed for extra comfort. Cement waterproof construction... Men's Johnston & Murphy Branning Chukka Boot - Black Waterproof Calfskin Boots

Men's Johnston & Murphy Branning...

Shoebuy.com
Johnston & Murphy
$184.95
Free Shipping
Take on any adventure wearing the Sperry Fowl Weather Chukka Boot. Its seam-sealed, waterproof upper with a gusseted tongue keeps you protected. This boot has a molded rubber outsole with... Men's Sperry Top-Sider Fowl Weather Chukka Boot - Black Waterproof Leather Boots

Men's Sperry Top-Sider Fowl Weather...

Shoebuy.com
Sperry Top-Sider
$89.95
Free Shipping
Your commute to work should be a breeze, let the City Smart - H20 Dress Chukka Boot keep your feet dry and comfortable. ; Made with premium seam sealed Hydro-Shield waterproof leather to... Rockport - City Smart - Waterproof Dress Chukka Boot (Black Waterproof) Men's Boots

Rockport - City Smart - Waterproof...

Zappos.com
Rockport
$159.95
Free Shipping
Fully cushioned from heel to toe, these handsome leather chukka boots can easily handle tough weather conditions. construction leather upper rubber sole details lace up memory foam footbed Florsheim NDNS Mens Waterproof Leather Chukka Boots

Florsheim NDNS Mens Waterproof...

jcpenney
Florsheim
$130.00
Free Shipping
Fully cushioned from heel to toe, these handsome leather chukka boots can easily handle tough weather conditions. construction leather upper rubber sole details lace up memory foam footbed Florsheim NDNS Mens Waterproof Leather Chukka Boots

Florsheim NDNS Mens Waterproof...

jcpenney
Florsheim
$130.00
Free Shipping
The tough, stylish leather and reliable outsole of the Madson Chukka from Sorel keeps you walking steady on both the city sidewalks and those urban trails. ; Waterproof suede leather upper.... SOREL - Madson Chukka (Crouton) Men's Waterproof Boots

SOREL - Madson Chukka (Crouton) Men's...

Zappos.com
Sorel
$170.00
Free Shipping
Wolverine 6 Waterproof Chukka Work Boots Offer a relaxed, mid - height style. Comfortable Chukka Work Boots with rugged soles. These Men's 6 Waterproof Chukka Work Boots have a special... Wolverine Men's 6 inch Waterproof Chukka Boots Gold, Size: 8d

Wolverine Men's 6 inch Waterproof...

The Sportsman's Guide
Wolverine
$119.99
Wolverine 6 Waterproof Chukka Work Boots Offer a relaxed, mid - height style. Comfortable Chukka Work Boots with rugged soles. These Men's 6 Waterproof Chukka Work Boots have a special... Wolverine Men's 6 inch Waterproof Chukka Boots Gold, Size: 9d

Wolverine Men's 6 inch Waterproof...

The Sportsman's Guide
Wolverine
$119.99
The Rocky 6in. Western Cruiser Chukka Casual Boot has been built with high quality full-grain leather. The interior will remain dry, even in unpleasant weather conditions, because it has... Rocky 6 Inch Western Cruiser Chukka Casual Boot - Brown, Size 8 Wide, Model 2984

Rocky 6 Inch Western Cruiser Chukka...

Northern Tool
Rocky
$149.99
The Rocky 6in. Western Cruiser Chukka Casual Boot has been built with high quality full-grain leather. The interior will remain dry, even in unpleasant weather conditions, because it has... Rocky 6 Inch Western Cruiser Chukka Casual Boot - Brown, Size 10 Wide, Model 2984

Rocky 6 Inch Western Cruiser Chukka...

Northern Tool
Rocky
$149.99
Up, down and on your feet all day means you demand a perfect package of durable comfort without the weight. Enter this steadfast work boot. A friend to your feet, its waterproof... Wolverine Gold Waterproof Chukka Work Boot Gold Nubuck/Dark Brown, Size 12EW

Wolverine Gold Waterproof Chukka Work...

Wolverine
Wolverine
$135.00
Up, down and on your feet all day means you demand a perfect package of durable comfort without the weight. Enter this steadfast work boot. A friend to your feet, its waterproof... Wolverine Gold Waterproof Chukka Work Boot Gold Nubuck/Dark Brown, Size 8M

Wolverine Gold Waterproof Chukka Work...

Wolverine
Wolverine
$135.00
Don't let heavy loose boots or big awkward laces keep you from a minute of winter fun. Slide Sorel's Paxson Chukka Waterproof Boot on and get out there in a hurry. This boot gets its good... Sorel Paxson Chukka Waterproof Boot Men's

Sorel Paxson Chukka Waterproof Boot...

Peter Glenn
Sorel
$109.99
Free Shipping
CLOSEOUTS . Timberland's Earthkeepers Gorham chukka boots combine laid-back chukka style in buttery-soft leather with hardcore waterproof protection. The lugged Vibram® rubber outsole... Timberland Earthkeepers Gorham Chukka Boots - Waterproof, Leather (For Men) – BROWN

Timberland Earthkeepers Gorham Chukka...

Sierra Trading Post
Timberland
$140.00 $89.95

36%

Off
CLOSEOUTS . Puddles and slushy streets are no match for Hush Puppies' Dutch Abbott chukka boots. The waterproof leather upper is seam sealed for complete waterproof protection, and... Hush Puppies Dutch Abbott Leather Chukka Boots - Waterproof, Insulated (For Men) – BLACK LEATHER

Hush Puppies Dutch Abbott Leather...

Sierra Trading Post
Hush Puppies
$159.00 $49.95

69%

Off
Sizing: True to size. , Moc toe with bumper, Wraparound lacing, Lace-up vamp closure, Removable padded insole, Back pull-tab, Rubber bumper and sole, Waterproof, Approx. 4" shaft height,... Sperry Boatyard Chukka Boot - Waterproof at Nordstrom Rack - Mens Shoes - Mens Casual Boots - Footwe

Sperry Boatyard Chukka Boot -...

Nordstrom Rack
Sperry Top-Sider
$150.00 $79.97

47%

Off
Sizing: True to size. , Moc toe with bumper, Wraparound lacing, Lace-up vamp closure, Removable padded insole, Back pull-tab, Rubber bumper and sole, Waterproof, Approx. 4" shaft height,... Sperry Boatyard Chukka Boot - Waterproof at Nordstrom Rack - Mens Shoes - Mens Casual Boots - Footwe

Sperry Boatyard Chukka Boot -...

Nordstrom Rack
Sperry Top-Sider
$150.00 $79.97

47%

Off
Take on any adventure wearing the Sperry Fowl Weather Chukka Boot. Its seam-sealed, waterproof upper with a gusseted tongue keeps you protected. This boot has a molded rubber outsole with... Men's Sperry Top-Sider Fowl Weather Chukka Boot - Navy Waterproof Leather Boots

Men's Sperry Top-Sider Fowl Weather...

Shoebuy.com
Sperry Top-Sider
$89.95
Free Shipping
Take on any adventure wearing the Sperry Fowl Weather Chukka Boot. Its seam-sealed, waterproof upper with a gusseted tongue keeps you protected. This boot has a molded rubber outsole with... Men's Sperry Top-Sider Fowl Weather Chukka Boot - Dark Brown Waterproof Leather Boots

Men's Sperry Top-Sider Fowl Weather...

Shoebuy.com
Sperry Top-Sider
$89.95
Free Shipping
Contrast rubber sole adds interest to suede boot. Suede upper. Almond toe. Lace-up vamp. Leather lining. Rubber sole. Padded insole. Made in Italy. - Color: Coastal-Graphite - Sizes: 110... Vince Jackson Suede Chukka Boots - Coastal-Graphite : Vince Shoes

Vince Jackson Suede Chukka Boots -...

Saks Fifth Ave
$395.00
Refined chukka boots rendered in fine calf leather. Italian calf leather upper. Lace-up closure. Leather lining and sole. Padded insole. Made in Italy. - Color: Luggage - Sizes: 12 M,8 M,9... Vince Alberto Calf Leather Chukka Boots - Luggage : Vince Shoes

Vince Alberto Calf Leather Chukka...

Saks Fifth Ave
$395.00
Dapper suede chukka boots in high-top silhouette. Suede upper. Heel pull tab. Lace-up closure. Leather lining. Rubber sole. Made in Italy. - Color: Dark Brown - Sizes:... Tod's Polacco Gomma Suede Chukka Boots - Dark Brown : Tod's Shoes

Tod's Polacco Gomma Suede Chukka...

Saks Fifth Ave
Tod's
$495.00
Add a touch of style to your look with the Timberland Brook Park Insulated Waterproof Chukka Boot. Crafted with waterproof materials, this boot keeps the foot dry all day long. With 100... Men's Timberland Brook Park Insulated Waterproof Chukka Boot Boots

Men's Timberland Brook Park Insulated...

Shoebuy.com
Timberland
$149.95
Free Shipping
The Essential Details Waterproof Chukka Boot features a comfort system designed to provide lightweight shock absorption, Hydro-Shield construction to help keep the feet dry and comfortable... Men's Rockport Essential Details Waterproof Chukka Boot Boots

Men's Rockport Essential Details...

Shoebuy.com
Rockport
$109.95
Free Shipping
Add a touch of style to your look with the Timberland Brook Park Insulated Waterproof Chukka Boot. Crafted with waterproof materials, this boot keeps the foot dry all day long. With 100... Men's Timberland Brook Park Insulated Waterproof Chukka Boot Boots

Men's Timberland Brook Park Insulated...

Shoebuy.com
Timberland
$149.95
Free Shipping
The rugged Sperry A/O Lug Boat Waterproof Chukka Boot is ideal for everything casual. Its waterproof construction repels moisture to keep your foot dry and the genuine handsewn upper... Men's Sperry Top-Sider A/O Lug Boat Waterproof Chukka Boot Boots

Men's Sperry Top-Sider A/O Lug Boat...

Shoebuy.com
Sperry Top-Sider
$139.95
Free Shipping
The rugged Sperry A/O Lug Boat Waterproof Chukka Boot is ideal for everything casual. Its waterproof construction repels moisture to keep your foot dry and the genuine handsewn upper... Men's Sperry Top-Sider A/O Lug Boat Waterproof Chukka Boot Boots

Men's Sperry Top-Sider A/O Lug Boat...

Shoebuy.com
Sperry Top-Sider
$139.95
Free Shipping
For a classic look, go to the Jay C. Chukka Boot. It features a burnished upper, laces for a good fit, ankle pull tab for easy on/easy off, faux leather lining, cushiony memory foam insole... Men's Jay C. Chukka Boot

Men's Jay C. Chukka Boot

Payless.com
Dexter
$49.99 $39.99
For a classic look, go to the Jay C. Chukka Boot. It features a burnished upper, laces for a good fit, ankle pull tab for easy on/easy off, faux leather lining, cushiony memory foam insole... Men's Jay C. Chukka Boot

Men's Jay C. Chukka Boot

Payless.com
Dexter
$49.99 $39.99
For a classic look, go to the Jay C. Chukka Boot. It features a burnished upper, laces for a good fit, ankle pull tab for easy on/easy off, faux leather lining, cushiony memory foam insole... Men's Jay C. Chukka Boot

Men's Jay C. Chukka Boot

Payless.com
Dexter
$49.99 $39.99