Sperry Authentic Original Waterproof Lug Chukka Boots offer rugged, nautical-inspired style in lace-up boots. These Sperry waterproof boots feature hand-sewn leather uppers and... Sperry Authentic Original Waterproof Lug Chukka Boots for Men

Sperry Authentic Original Waterproof...

Bass Pro Shops
Sperry
$159.99
Expand your horizons in comfort and style with these Skechers Relaxed Fit chukka boots. Boot Features Waterproof upper High traction outsole Padded collar and tongue Relaxed Fit design for... Skechers Relaxed Fit Segment Melego Men's Waterproof Chukka Boots

Skechers Relaxed Fit Segment Melego...

Kohl's
$95.00 $78.99
At Bass Pro Shops�, we constantly strive to create products that enhance your on-the-water experience. We created our new line of quick-drying, water-friendly World Wide Sportsman� Blue... World Wide Sportsman Blue Water Waterproof Chukka Boots for Men - Tan - 10 W

World Wide Sportsman Blue Water...

Bass Pro Shops
$89.99
Wet, sloppy conditions? Bring it on! Because these classic, classy Chukkas say inchMission Accomplished inch when it comes to guaranteed dry comfort to wear anywhere. They feature Irish... Irish Setter Men's SoftPaw Waterproof Chukka Boots Brown, 8.5 2e

Irish Setter Men's SoftPaw Waterproof...

Sportsman's Guide
Irish Setter
$154.99
"TOMS Waterproof Chukka Boots. Bursting with casual style, these incredible boots feature a premium waterproof leather with an inner waterproof liner to keep your feet dry and comfortable... TOMS Waterproof Chukka Boots

TOMS Waterproof Chukka Boots

Belk
TOMS
$129.00 $96.75

25%

Off
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 7M

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 8.5EW

Wolverine Gold Waterproof Chukka Work...

Wolverine
Wolverine
$135.00
Artfully blending rugged and refined, the Timberland Men's Willoughby Waterproof Chukka Boot boasts clean lines, stunning leather, and a timeless workboot aesthetic. A slightly different... Willoughby Waterproof Chukka Boot - Men's

Willoughby Waterproof Chukka Boot -...

Backcountry.com
Timberland
$169.95
Artfully blending rugged and refined, the Timberland Men's Willoughby Waterproof Chukka Boot boasts clean lines, stunning leather, and a timeless workboot aesthetic. A slightly different... Willoughby Waterproof Chukka Boot - Men's

Willoughby Waterproof Chukka Boot -...

Backcountry.com
Timberland
$169.95
Features:Tractor tread rubber outsolesContain activated charcoalHand made rubber bottoms The Chukka Boots from Kenetrek are a lighweight boot built with supportive 6oz leather that wraps so... Kenetrek Chukka Uninsulated Waterproof Boots Leather and Rubber Brown Men's 12

Kenetrek Chukka Uninsulated...

MidwayUSA
KeneTrek
$135.00
Wet, sloppy conditions? Bring it on! Because these classic, classy Chukkas say inchMission Accomplished inch when it comes to guaranteed dry comfort to wear anywhere. They feature Irish... Irish Setter Men's SoftPaw Waterproof Chukka Boots Brown, 9.5d

Irish Setter Men's SoftPaw Waterproof...

Sportsman's Guide
Irish Setter
$154.99
Great Pair Of Timberland Boots In Almost Brand New Condition (Worn Twice). Super Comfy, Warm And Waterproof + Really Cute Too! Make Me An Offer! Women'S Mt. Hayes Waterproof Chukka Boots

Women'S Mt. Hayes Waterproof Chukka...

Poshmark, Inc.
Timberland
$75.00
Features:Tractor tread rubber outsolesContain activated charcoalHand made rubber bottoms The Chukka Boots from Kenetrek are a lighweight boot built with supportive 6oz leather that wraps so... Kenetrek Chukka Uninsulated Waterproof Boots Leather and Rubber Brown Men's 8

Kenetrek Chukka Uninsulated...

MidwayUSA
KeneTrek
$135.00
Subtle embossing styles a handsome waterproof boot shaped from full-grain leather.Sizing: True to size. Cap toe. Lace-up vamp. Leather construction. Topstitched detail. Lug sole. Welt... Timberland West Haven Waterproof Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Casual Boots - Fo

Timberland West Haven Waterproof...

Nordstrom Rack
Timberland
$180.00 $89.97

50%

Off
Subtle embossing styles a handsome waterproof boot shaped from full-grain leather.Sizing: True to size. Cap toe. Lace-up vamp. Leather construction. Topstitched detail. Lug sole. Welt... Timberland West Haven Waterproof Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Casual Boots - Fo

Timberland West Haven Waterproof...

Nordstrom Rack
Timberland
$180.00 $89.97

50%

Off
Combining outdoor utility with modern styling, the Sorel Paxson Chukka Waterproof Casual Boot with seam sealed construction features a waterproof, full-grain leather upper and a felt-topped... Paxson Chukka Waterproof Casual Boot - Men's-Major/Black-Medium-11.5

Paxson Chukka Waterproof Casual Boot...

CampSaver.com
Sorel
$139.95 $83.97
Free Shipping

40%

Off
Combining outdoor utility with modern styling, the Sorel Paxson Chukka Waterproof Casual Boot with seam sealed construction features a waterproof, full-grain leather upper and a felt-topped... Paxson Chukka Waterproof Casual Boot - Men's-Major/Black-Medium-13

Paxson Chukka Waterproof Casual Boot...

CampSaver.com
Sorel
$139.95 $83.97
Free Shipping

40%

Off
You can depend on these Rocky TMC Postal Approved Duty Chukka work boots. Boot Features S.R. USA Postal approved Slip & oil resistant TMC Direct Attach TPU/PU outsole for stability &... Rocky TMC Postal Approved Duty Men's Chukka Work Boots

Rocky TMC Postal Approved Duty Men's...

Kohl's
$164.99
These casual and stylish chukka boots have a plain toe upper with a lightly pebbled finish. Superior fit. Waterproof. Cushioned footbed. Moisture wicking. Lightweight construction. Genuine... Johnston & Murphy Cardell Chukka Boots Men's Shoes

Johnston & Murphy Cardell Chukka...

Jos. A. Bank
$185.00
Free Shipping
The Chukka boots from Toms boast a full grain waterproof leather and suede upper, lace up fastening and warm lining. These Chukka Boots have a waterproof membrane to keep feet dry and... Mens Brown Chukka Boots

Mens Brown Chukka Boots

Trouva
$94.99 $49.00

48%

Off
The Chukka boots from TOMS boast a full grain waterproof leather and suede upper, lace up fastening and warm lining. These Chukka Boots have a waterproof membrane to keep feet dry and... Mens Black Chukka Boots

Mens Black Chukka Boots

Trouva
$94.99 $49.00

48%

Off
"Columbia Davenport Chukka Boot. Omni-Tech waterproof construction makes these boots perfect for the elements and beyond. Crafted with a classic full-grain leather upper and comfortable... Columbia Davenport Chukka Boot

Columbia Davenport Chukka Boot

Belk
Columbia
$130.00 $91.00

30%

Off
CLOSEOUTS . On-trend styling meets mid-top chukka design in Timberland's Groveton moc-toe chukka boots. The odor-resistant OrthoLite®-cushioned insole delivers all-day freshness, and the... Timberland Groveton Moc-Toe Chukka Boots - Nubuck (For Men) – WHEAT

Timberland Groveton Moc-Toe Chukka...

Sierra Trading Post
Timberland
$100.00 $59.99

40%

Off
At Bass Pro Shops�, we constantly strive to create products that enhance your on-the-water experience. We created our new line of quick-drying, water-friendly World Wide Sportsman� Blue... World Wide Sportsman Blue Water Waterproof Chukka Boots for Men - Tan - 11 M

World Wide Sportsman Blue Water...

Bass Pro Shops
$89.99
At Bass Pro Shops�, we constantly strive to create products that enhance your on-the-water experience. We created our new line of quick-drying, water-friendly World Wide Sportsman� Blue... World Wide Sportsman Blue Water Waterproof Chukka Boots for Men - Tan

World Wide Sportsman Blue Water...

Bass Pro Shops
$89.99
CLOSEOUTS . Scarpa Daylite Gore-Tex® hiking boots are lightweight backpacking boots that capably handle any weather and virtually any terrain. The waterproof breathable upper has a collar... Scarpa Daylite Gore-Tex® Hiking Boots- Waterproof (For Men) – DARK BROWN/CHARCOAL

Scarpa Daylite Gore-Tex® Hiking...

Sierra Trading Post
Scarpa
$219.00 $139.99

36%

Off
CLOSEOUTS . If you're the kind of adventurer who enjoys taking a hike on the wild side, allow Trezeta's Adventure hiking boots to keep your feet dry and comfortable while you explore the... Trezeta Adventure Hiking Boots - Waterproof (For Men) – CARIBOU/RED

Trezeta Adventure Hiking Boots -...

Sierra Trading Post
$150.00 $79.99

47%

Off
A great look for autumn and cool nights near the water, Authentic Original Waterproof Lug Chukka Boots deliver 100% waterproof protection with that classic Sperry look. Providing dry... Sperry Authentic Original Waterproof Lug Chukka Boots for Men

Sperry Authentic Original Waterproof...

Bass Pro Shops
Sperry
$134.99
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 12M

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 11.5EW

Wolverine Gold Waterproof Chukka Work...

Wolverine
Wolverine
$135.00