This funky lace-up is the answer to the traditional chukka. With a nylon upper, KEEN. DRY waterproof, breathable membrane, rugged mud guard, and higher-traction grip outsole, you can push... Keen Men's Waterproof Glieser Chukka Nylon Boots Size 7.5, In Black

Keen Men's Waterproof Glieser Chukka...

Keen Footwear
Keen
$120.00 $89.99

25%

Off
Dockers Landers Casual Boots. These versatile, casual rugged lace-up boots from Dockers is an easy choice to pair with jeans or khakis for go-to casual or weekend wear. Dockers Dark Tan Landers Casual Boots

Dockers Dark Tan Landers Casual Boots

Belk
Dockers
$110.00 $82.50

25%

Off
Dockers Landers Casual Boots. These versatile, casual rugged lace-up boots from Dockers is an easy choice to pair with jeans or khakis for go-to casual or weekend wear. Dockers Dark Tan Landers Casual Boots

Dockers Dark Tan Landers Casual Boots

Belk
Dockers
$110.00 $82.50

25%

Off
Shoes by Timberland. Comes in Wheat, Size 11. 5 W. The boots that are recognized everywhere. Premium leather with direct-attach, seam-sealed waterproof construction and 200 grams of... Men's Timberland Icon Waterproof Chukkas, Tan, Size 11.5 Wide Width

Men's Timberland Icon Waterproof...

Blair.com
Timberland
$159.99
Dockers Landers Casual Boots. These versatile, casual rugged lace-up boots from Dockers is an easy choice to pair with jeans or khakis for go-to casual or weekend wear. Dockers Dark Tan Landers Casual Boots

Dockers Dark Tan Landers Casual Boots

Belk
Dockers
$110.00 $82.50

25%

Off
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,... Mens Spring Step Men Mathias Chukka Boots - Black Black

Mens Spring Step Men Mathias Chukka...

Boscov's
Spring Step
$99.99
Shoes by Timberland. Comes in Wheat, Size 10 W. The boots that are recognized everywhere. Premium leather with direct-attach, seam-sealed waterproof construction and 200 grams of PrimaLoft... Men's Timberland Icon Waterproof Chukkas, Tan, Size 10 Wide Width

Men's Timberland Icon Waterproof...

Blair.com
Timberland
$159.99
The unfussy lines of the Eastland Jack Chukka Boot are finished with a full-grain leather that only gets better with time. A mini-groove sole design provides traction, flexibility and... Men's Eastland Jack Chukka Boot - Peanut Leather Boots

Men's Eastland Jack Chukka Boot -...

shoes.com
Eastland
$124.95
Free Shipping
Shoes by Timberland. Comes in Wheat, Size 8. 5 W. The boots that are recognized everywhere. Premium leather with direct-attach, seam-sealed waterproof construction and 200 grams of... Men's Timberland Icon Waterproof Chukkas, Tan, Size 8.5 Wide Width

Men's Timberland Icon Waterproof...

Blair.com
Timberland
$159.99
The Galloway Chukka Boot from Nunn Bush sports a clean, masculine finish with a comfort footbed featuring memory foam and open cell foam. Suede leather upper Dual Comfort footbed featuring... Men's Nunn Bush Galloway Chukka Boot - Beige Suede Boots

Men's Nunn Bush Galloway Chukka Boot...

shoes.com
Nunn Bush
$64.95
Free Shipping
The smart and sophisticated Altra Smith Chukka Boot II features a flat outsole and a FootShape™ toe box that gives your toes room to relax and spread out for incredible comfort and freedom.... Men's Altra Footwear Smith Chukka Boot II - Brown Boots

Men's Altra Footwear Smith Chukka...

shoes.com
Altra
$129.95
Free Shipping
*Casual by nature, comfortable by design, the Barklay Plain Toe Chukka Boot is perfect for the modern man *Genuine leather upper *Lace-up closure *Striped fabric lining *Molded Comfort Gel... Nunn Bush Barklay Plain Toe Chukka Boot - Mens 11.5 Tan Boot Medium

Nunn Bush Barklay Plain Toe Chukka...

ShoeMall.com
Nunn Bush
$84.95
Free Shipping
*The Irvine Chukka Boot is perfect for everyday wear as well as for nicer events *Synthetic leather upper with microsuede details *Lace-up styling for a personalized fit *Breathable fabric... Deer Stags Irvine Chukka Boot - Mens 13 Brown Boot Medium

Deer Stags Irvine Chukka Boot - Mens...

ShoeMall.com
Deer Stags
$79.95
Free Shipping
*This lightweight leather chukka features all the comfort, cushioning and flexibility of a quality walking shoe *"Pull-up" leather upper *FOOTONIC II® contoured cushioned insert is... Walkabout Men's Chukka Boot - 14 Brown Oxford D

Walkabout Men's Chukka Boot - 14...

ShoeMall.com
Walkabout Footwear
$114.95
Free Shipping
Sorel Footwear Madson Chukka Waterproof Casual Boot - Mens Quarry/Fawn 13 Model: 1775851052-13. Sorel Madson Chukka Waterproof Casual Boot - Mens Quarry/Fawn 13 1775851052-13 Sorel Footwear Madson Chukka Waterproof Casual Boot - Mens Quarry/Fawn 13 Model: 1775851052-13

Sorel Footwear Madson Chukka...

CampSaver.com
Sorel
$170.00
Free Shipping
Sorel Footwear Ace Chukka Waterproof Boots - Men's Black Black 8.5 Model: 1869581010-8-5. 5 1869581010-8.5 Sorel Footwear Ace Chukka Waterproof Boots - Men's Black Black 8.5 Model: 1869581010-8-5

Sorel Footwear Ace Chukka Waterproof...

CampSaver.com
Sorel
$93.13
Free Shipping
Sorel Footwear Ace Chukka Waterproof Boots - Men's Black Black 7.5 Model: 1869581010-7-5. 5 1869581010-7.5 Sorel Footwear Ace Chukka Waterproof Boots - Men's Black Black 7.5 Model: 1869581010-7-5

Sorel Footwear Ace Chukka Waterproof...

CampSaver.com
Sorel
$92.11
Free Shipping
Possibly the lightest, most comfortable chukka boot you’ll ever wear. With its flexible, lightweight design and versatile style, this boot is ready for any urban adventure. | Keen Men's... Keen Men's Grayson Chukka Boots Size 10, In Mid Brown/Scylum Full-Grain

Keen Men's Grayson Chukka Boots Size...

Keen Footwear
Keen
$135.00 $76.99

43%

Off
Eastland Jack Chukka Leather Boot - Brown US 9, Men's Peanut Distressed leather lace-up boot Active Memory Foam footbed conforms to the curves of your foot Mini-groove sole design provides... Eastland Jack Chukka Leather Boot - Brown US 9, Men's

Eastland Jack Chukka Leather Boot -...

Buckle.com
Eastland
$99.95
These Mens Propet(R) Findley chukka boots showcase a plain toe lace up style with suede uppers and soft flannel lining. They include removable open-cell foam insoles with durable rubber... Mens Propet(R) Findley Chukka Boots Tan

Mens Propet(R) Findley Chukka Boots...

Boscov's
Propet
$94.95
To help you accomplish the daily tasks, you should wear these men's Georgia Boot Farm and Ranch chukka work boots. In barracuda gold.SHOE FEATURES SPR leather for durability Goodyear welt... Georgia Boot Farm & Ranch Men's Wedge Chukka Boots, Size: 10.5 Wide, Brown

Georgia Boot Farm & Ranch Men's Wedge...

Kohl's
Georgia
$137.00
Free Shipping
To help you accomplish the daily tasks, you should wear these men's Georgia Boot Farm and Ranch chukka work boots. In barracuda gold.SHOE FEATURES SPR leather for durability Goodyear welt... Georgia Boot Farm & Ranch Men's Wedge Chukka Boots, Size: 9.5 Wide, Brown

Georgia Boot Farm & Ranch Men's Wedge...

Kohl's
Georgia
$137.00
Free Shipping
To help you accomplish the daily tasks, you should wear these men's Georgia Boot Farm and Ranch chukka work boots. In barracuda gold.SHOE FEATURES SPR leather for durability Goodyear welt... Georgia Boot Farm & Ranch Men's Wedge Chukka Boots, Size: Medium (8.5), Brown

Georgia Boot Farm & Ranch Men's Wedge...

Kohl's
Georgia
$137.00
Free Shipping
It's officially up to you to draw the line between house shoe and slipper boot. Between toasty feet, a sturdy outsole, and a cool, chukka boot style, you won't have to sacrifice comfort... Keen Men's Howser Quilted Chukka Shoes Size 8.5, In Steel Grey/Raven

Keen Men's Howser Quilted Chukka...

Keen Footwear
Keen
$90.00 $64.99

28%

Off
Deer Stags Walkmaster Chukka Boots. You don't have to compromise comfort to look great. The Deer Stags Walkmaster series shoes will be your secret weapon, letting you feel and look like a... Deer Stags Black Walkmaster Chukka Boots

Deer Stags Black Walkmaster Chukka...

Belk
Deer Stags
$90.00 $57.37

36%

Off
Timberland Squall Canyon Chukka Boot. A classic chukka silhouette with laces creates this leather boot from Timberland. Timberland Potting Soil Squall Canyon Chukka Boot

Timberland Potting Soil Squall Canyon...

Belk
Timberland
$150.00 $112.50
Free Shipping

25%

Off
Deer Stags Walkmaster Chukka Boots. You don't have to compromise comfort to look great. The Deer Stags Walkmaster series shoes will be your secret weapon, letting you feel and look like a... Deer Stags Black Walkmaster Chukka Boots

Deer Stags Black Walkmaster Chukka...

Belk
Deer Stags
$90.00 $57.37

36%

Off
From office to happy hour, the Clarks Grandin Top Chukka Boot keeps you comfortable all-day long. This flexible boot is designed with OrthoLite® footbed that wicks away moisture and ensures... Men's Clarks Grandin Top Chukka Boot - Navy Suede Boots

Men's Clarks Grandin Top Chukka Boot...

shoes.com
Clarks
$76.95
Free Shipping
Stylish and laid-back, the Florsheim Edge Chukka Boot features elastic laces for an easy pull-on design. The removable footbed is fully cushioned for comfort, while the direct attach... Men's Florsheim Edge Chukka Boot - Olive Nubuck Boots

Men's Florsheim Edge Chukka Boot -...

shoes.com
Florsheim
$109.95
Free Shipping
Smart and on-trend the UGG Dustin Chukka Boot will be an ultimate addition to your footwear collection. The EVA insole with textile lining ensures cushioning and flexibility, while the... Men's UGG Dustin Chukka Boot - Black Suede Boots

Men's UGG Dustin Chukka Boot - Black...

shoes.com
UGG Australia
$74.95
Free Shipping