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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
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, 13d

Irish Setter Men's SoftPaw Waterproof...

Sportsman's Guide
Irish Setter
$159.99
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, 9.5d

Irish Setter Men's SoftPaw Waterproof...

Sportsman's Guide
Irish Setter
$159.99
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
$159.99
No matter what weather you find yourself in, these waterproof, full-grain leather chukkas will keep your feet dry and comfortable. Men's Casual [North Face, Northface, thenorthface, the... The North Face Men's Bridgeton Chukka Waterproof Boots (Size: 14): Rope Brown

The North Face Men's Bridgeton Chukka...

The North Face
The North Face
$160.00
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Rugged and casual, these waterproof leather boots are equally at home on city streets and in mountain towns. Crafted with IcePick temperature-sensitive lugs for sure footing on varied... The North Face Men's Ballard II Chukka Waterproof Boots (Size: 11): Museum Brown

The North Face Men's Ballard II...

The North Face
The North Face
$130.00
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Top-notch travel boots, these waterproof winter chukkas feature warm insulation and are finished with grippy soles for improved traction. Sale Shoe Sale [North Face, Northface,... The North Face Men's THERMOBALL Versa Chukkas II Waterproof Boots (Size: 12.5): Black (Past Season)

The North Face Men's THERMOBALL Versa...

The North Face
The North Face
$120.00 $84.00
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Waterproof, all-weather footwear with this season's stylish Chelsea boot silhouette and vintage-leather look: Sorel's "Paxson Chukka Waterproof Boot," a pull-on boot built with seam-sealed... Sorel Paxson Chukka Waterproof Men's Boot Outdoor

Sorel Paxson Chukka Waterproof Men's...

Infinity Shoes
$139.95
Waterproof, all-weather footwear with this season's stylish Chelsea boot silhouette and vintage-leather look: Sorel's "Paxson Chukka Waterproof Boot," a pull-on boot built with seam-sealed... Sorel Paxson Chukka Waterproof Men's Boot Outdoor

Sorel Paxson Chukka Waterproof Men's...

Infinity Shoes
$139.95
Sorel Footwear Madson Chukka Waterproof Suede Casual Boot Men's Camel Brown/Sea Salt 8 US. Sorel Madson Chukka Waterproof Suede Casual Boot Men's Camel Brown/Sea Salt 8 US 1775851224-8 Sorel Footwear Madson Chukka Waterproof Suede Casual Boot Men's Camel Brown/Sea Salt 8 US

Sorel Footwear Madson Chukka...

CampSaver.com
Sorel
$169.95
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Sorel Footwear Madson Chukka Waterproof Leather Casual Boot Men's Black/Black 10.5 US. 5 US 1767211011-10.5 Sorel Footwear Madson Chukka Waterproof Leather Casual Boot Men's Black/Black 10.5 US

Sorel Footwear Madson Chukka...

CampSaver.com
Sorel
$169.95
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Sorel Footwear Madson Chukka Waterproof Leather Casual Boot Men's Black/Black 9 US. Sorel Madson Chukka Waterproof Leather Casual Boot Men's Black/Black 9 US 1767211011-9 Sorel Footwear Madson Chukka Waterproof Leather Casual Boot Men's Black/Black 9 US

Sorel Footwear Madson Chukka...

CampSaver.com
Sorel
$169.95
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You can't be too careful when you say leather and waterproof in the same sentence but this immortal style in specially developed nubuck leather is fully waterproof.Sizing: True to size.... Swims Barry Classic Waterproof Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukka

Swims Barry Classic Waterproof Chukka...

Nordstrom Rack
Swims
$215.00 $99.00

54%

Off
You can't be too careful when you say leather and waterproof in the same sentence but this immortal style in specially developed nubuck leather is fully waterproof.Sizing: True to size.... Swims Barry Classic Waterproof Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukka

Swims Barry Classic Waterproof Chukka...

Nordstrom Rack
Swims
$215.00 $99.00

54%

Off
You can't be too careful when you say leather and waterproof in the same sentence but this immortal style in specially developed nubuck leather is fully waterproof.Sizing: True to size.... Swims Barry Classic Waterproof Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukka

Swims Barry Classic Waterproof Chukka...

Nordstrom Rack
Swims
$215.00 $99.00

54%

Off
UGG Leighton Waterproof Chukka Boot - Plain toe. Waterproof leather construction. Lace-up vamp. EnerG Comfort System insole. Crepe sole. Approx. 4" shaft height. Leather exterior, rubber... Leighton Waterproof Chukka Boot - Blue - UGG Boots

Leighton Waterproof Chukka Boot -...

Lyst
UGG Australia
$170.00 $100.00

41%

Off
Timberland City Waterproof Chukka Boot - Round toe. Waterproof leather construction. Lace-up vamp. Back pull-tab. Padded removable insole. Grip sole. Approx. 3.5" shaft height. Leather... City Waterproof Chukka Boot - Black - Timberland Boots

City Waterproof Chukka Boot - Black -...

Lyst
Timberland
$120.00 $70.00

42%

Off
Florsheim Midtown Waterproof Chukka Boot - Timeless style meets weather-ready performance in the Midtown Waterproof Chukka Boot from Florsheim®. Waterproof full-grain leather uppers and... Midtown Waterproof Chukka Boot - Black - Florsheim Boots

Midtown Waterproof Chukka Boot -...

Lyst
Florsheim
$125.00
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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
*Travel in style and comfort with this waterproof winter chukka *Waterproof, BLC-compliant full-grain leather upper *4" upper height *Lace-up closure *PrimaLoft® ThermoBall™ collar... The North Face ThermoBall Versa Chukka II - Mens 8.5 Black Boot Medium

The North Face ThermoBall Versa...

ShoeMall.com
The North Face
$119.95
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Full-grain leather upper, Lined for comfort, Leather footbed, Lightweight construction for all-day comfort, Waterproof, Rubber outsole, Not eligible for promotions, Ships only within the... Wolverine Cort Chukka Boot

Wolverine Cort Chukka Boot

American Eagle Outfitters
$170.00
A casual classic, Sorel Madson Chukka Outdoor Boot features a seam-sealed waterproof construction and sneaker-life comfort, with a rich waterproof leather and suede upper, Die cut EVA... Sorel Madson Chukka Men's Outdoor Boot

Sorel Madson Chukka Men's Outdoor Boot

Infinity Shoes
$170.00
Full-grain leather upper, Lined for comfort, Leather footbed, Lightweight construction for all-day comfort, Waterproof, Rubber outsole, Not eligible for promotions, Ships only within the... Wolverine Cort Chukka Boot

Wolverine Cort Chukka Boot

American Eagle Outfitters
$170.00
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, 14 2e

Irish Setter Men's SoftPaw Waterproof...

Sportsman's Guide
Irish Setter
$159.99
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, 11d

Irish Setter Men's SoftPaw Waterproof...

Sportsman's Guide
Irish Setter
$159.99
Top-notch travel boots, these waterproof winter chukkas feature warm insulation and are finished with grippy soles for improved traction. Sale Shoe Sale [North Face, Northface,... The North Face Men's THERMOBALL Versa Chukkas II Waterproof Boots (Size: 13): Black (Past Season)

The North Face Men's THERMOBALL Versa...

The North Face
The North Face
$120.00 $84.00
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30%

Off
No matter what weather you find yourself in, these waterproof, full-grain leather chukkas will keep your feet dry and comfortable. Men's Casual [North Face, Northface, thenorthface, the... The North Face Men's Bridgeton Chukka Waterproof Boots (Size: 7.5): Bone Brown

The North Face Men's Bridgeton Chukka...

The North Face
The North Face
$160.00
Free Shipping
No matter what weather you find yourself in, these waterproof, full-grain leather chukkas will keep your feet dry and comfortable. Men's Casual [North Face, Northface, thenorthface, the... The North Face Men's Bridgeton Chukka Waterproof Boots (Size: 7.5): Rope Brown

The North Face Men's Bridgeton Chukka...

The North Face
The North Face
$160.00
Free Shipping
Rugged and casual, these waterproof leather boots are equally at home on city streets and in mountain towns. Crafted with IcePick temperature-sensitive lugs for sure footing on varied... The North Face Men's Ballard II Chukka Waterproof Boots (Size: 9): Museum Brown

The North Face Men's Ballard II...

The North Face
The North Face
$130.00
Free Shipping
No matter what weather you find yourself in, these waterproof, full-grain leather chukkas will keep your feet dry and comfortable. Men's Casual [North Face, Northface, thenorthface, the... The North Face Men's Bridgeton Chukka Waterproof Boots (Size: 10): Rope Brown

The North Face Men's Bridgeton Chukka...

The North Face
The North Face
$160.00
Free Shipping