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Sperry Cutwater Chukka Rubber (Olive) Men's Boots

Sperry Cutwater Chukka Rubber (Olive) Men's Boots

When the weather turns head out in this insulated wet-weather Sperry Cutwater Chukka Rubber boot with the look and feel of a modern sneaker! Modern sneaker meets insulated wet-weather boot. Molded rubber upper. Five-eyelet lacing for a secure fit.... more

$110.00 $42.99

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Xray Men's The Windom Casual Chukka Boot 11 Brown Medium

Xray Men's The Windom Casual Chukka Boot 11 Brown Medium

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.98 $34.99

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Best Seller
Xray Men's The Windom Casual Chukka Boot 8.5 Brown Medium

Xray Men's The Windom Casual Chukka Boot 8.5 Brown Medium

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.98 $34.99

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Xray Men's The Windom Casual Chukka Boot 10 Brown Medium

Xray Men's The Windom Casual Chukka Boot 10 Brown Medium

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.98 $34.99

FREE shipping

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Xray Men's The Windom Casual Chukka Boot

Xray Men's The Windom Casual Chukka Boot

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.99 $36.00

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Xray Men's The Windom Casual Chukka Boot

Xray Men's The Windom Casual Chukka Boot

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.99 $36.00

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Xray Men's The Windom Casual Chukka Boot

Xray Men's The Windom Casual Chukka Boot

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.99 $36.00

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Guide Gear Men’s Pursuit II 9 inch Waterproof Insulated Camo Hunting Boots 400 Gram, 9.5 2e, Mossy Oak Break-Up Country

Guide Gear Men’s Pursuit II 9 inch Waterproof Insulated Camo Hunting Boots 400 Gram, 9.5 2e, Mossy Oak Break-Up Country

More. For less. How do you get it? It’s simple. You buy Guide Gear. When it’s time to invest in a new pair of boots for cold-weather hunting and outdoor pursuits, we suggest Guide Gear Pursuit Men’s Camo 9” Hunting Boots with 400 gram Thinsulate Ultra... more

$119.99 $54.09

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Guide Gear Men’s Pursuit II 9 inch Waterproof Insulated Camo Hunting Boots 400 Gram, 8.5 2e, Mossy Oak Break-Up Country

Guide Gear Men’s Pursuit II 9 inch Waterproof Insulated Camo Hunting Boots 400 Gram, 8.5 2e, Mossy Oak Break-Up Country

More. For less. How do you get it? It’s simple. You buy Guide Gear. When it’s time to invest in a new pair of boots for cold-weather hunting and outdoor pursuits, we suggest Guide Gear Pursuit Men’s Camo 9” Hunting Boots with 400 gram Thinsulate Ultra... more

$119.99 $54.09

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Guide Gear Men's Silvercliff II Insulated Waterproof Boots, 11.5 2e, Brown

Guide Gear Men's Silvercliff II Insulated Waterproof Boots, 11.5 2e, Brown

These light-on-your feet Silvercliffs zip tight in seconds for a winter-ready departure in record time. And they come off just as quick to avoid tracking outdoor slop where it doesn't belong. 100% waterproof against driving rain, freezing slush, snow... more

$69.99 $59.99

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Men's Twin Gore Pull-On Duck Boot by Haband, Brown, Size 11

Men's Twin Gore Pull-On Duck Boot by Haband, Brown, Size 11

Shoes by Haband. Comes in Brown, Size 11 M. 100% Waterproof Shell, Genuine Leather Upper with wide gore elastic for perfect fit. Thinsulate® Insulated. Anti-Slip Traction Outsole. Defined Heel. *Shipped by the manufacturer. more

$99.99

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Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 Wide, Model GB1222

Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 Wide, Model GB1222

These Georgia Farm & Ranch Chukka work boots are ideal for accomplishing daily tasks on the farm. The uppers are built with rugged SPR full-grain leather, which resists caustic chemicals and barnyard acids and is much stronger than traditional... more

$124.99

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Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 1/2 Wide, Model GB1222

Georgia Men's Farm & Ranch Chukka Work Boots - Barracuda Gold, Size 9 1/2 Wide, Model GB1222

These Georgia Farm & Ranch Chukka work boots are ideal for accomplishing daily tasks on the farm. The uppers are built with rugged SPR full-grain leather, which resists caustic chemicals and barnyard acids and is much stronger than traditional... more

$124.99

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Kenetrek Mountain Extremes 10" Waterproof 400 Gram Insulated Hunting Boots Leather and Nylon Brown Men's 10.5 E

Kenetrek Mountain Extremes 10" Waterproof 400 Gram Insulated Hunting Boots Leather and Nylon Brown Men's 10.5 E

Features2.8 mm Top grain leatherK-Talon outsolesWaterproof, Breathable Windtex membrane400 grams of Thinsulate InsulationA serious boot for rugged terrain, the 10" Kenetrek Mountain Extreme is made with a one piece vamp of 2.8 mm top grain leather on... more

$479.95

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MidwayUSA

(950,000+)
Men's Rockport Classic Break Chukka Boot - Dark Brown Leather Boots

Men's Rockport Classic Break Chukka Boot - Dark Brown Leather Boots

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For the young Urban professional who wants business attire with a little attitude. Sophisticated and fashion-forward, the Chukka Boot from Rockport's Classic Break Collection offers a bevy of mod work-to-weekend profiles that pack enough personality to... more

$120.00 $106.45

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shoes.com

(175,000+)
Men's Ariat Conquest Round Toe H2O Insulated 400G Cowboy Boot Boots

Men's Ariat Conquest Round Toe H2O Insulated 400G Cowboy Boot Boots

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Ariat's Conquest Round Toe H2O Insulated 400G Cowboy Boot is the perfect choice for outdoor activities. The Duratread™ outsole offers wear-resistance and flexibility, and the ATS® Pro technology that features a lightweight, composite forked shank... more

$189.95

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shoes.com

(175,000+)
Muck Wetland 16.5" Waterproof Insulated Hunting Boots Rubber and Nylon Bark Men's 15 D

Muck Wetland 16.5" Waterproof Insulated Hunting Boots Rubber and Nylon Bark Men's 15 D

FeaturesComfort rating of -20 to 50 FAnti-microbialWrap-up toe bumper5mm nylon bootieThe Muck Wetland boot is ideal for mid to late season wear while in the woods or the swamp. With a 5mm CR flex-foam bootie, the Wetland features a comfort rating of... more

$154.95

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MidwayUSA

(950,000+)
Muck Chore Mid 12" Waterproof Insulated Work Boots Rubber and Nylon Black Men's 11 D

Muck Chore Mid 12" Waterproof Insulated Work Boots Rubber and Nylon Black Men's 11 D

FeaturesStretch-fit topline binding snugs calf to keep warmth in and cold out 5mm CR flex-foam bootie with four-way stretch nylon, 100% waterproof, lightweight and flexible Seamless, quick-clean rubber overlay Additional achilles reinforcement for... more

$99.95

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MidwayUSA

(950,000+)
Men's Baffin Impact Snow Boot - Snow Camo Boots

Men's Baffin Impact Snow Boot - Snow Camo Boots

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Keep your feet toasty and dry with the Impact Snow Boot. The insulated nylon upper has reflective piping, a built-in locking snow collar, and easily adjustable double buckle closures. The added benefit of Baffin's removable multi-layer inner boot... more

$156.95

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shoes.com

(175,000+)
Fin & Feather Men's Chukka Brown Boot 13 E

Fin & Feather Men's Chukka Brown Boot 13 E

*Footwear designed to take you off the trail where the going can be treacherous *Tumbled full grain leather upper *Multi-layer CUSH-N-EEZ® construction for added stability and shock-absorbency *Velvet-eez® cushioned innersole *DRI-LEX® two-zone comfort... more

$125.95

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ShoeMall.com

(50,000+)
Work America Men's Work Chukka Black Boot 13 E

Work America Men's Work Chukka Black Boot 13 E

*WORK AMERICA's premium leather chukka is sturdy enough to hold up to rugged work conditions, yet comfortable enough for long hours on your feet *Premium leather upper *CUSH-N-CREPE Forward Glide® tapered sole is designed to enhance your natural... more

$114.95

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ShoeMall.com

(50,000+)
Muk Luks Charlie Men's Chukka Boots, Tan, 12 Medium

Muk Luks Charlie Men's Chukka Boots, Tan, 12 Medium

Muk Luks Mens Chukka Boots more

$104.00

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(25,000+)
Spring Step Men Mathias Chukka Boots - Black Black

Spring Step Men Mathias Chukka Boots - Black Black

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, durable cotton waxed laces, soft textile lining, a removable... more

$99.99

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Boscov's

(50,000+)
Men's Totes Insulated Boots, Black, Size 8.5

Men's Totes Insulated Boots, Black, Size 8.5

Shoes by Totes. Comes in Black, Size 8. 5 M. Perfect for rain, sleet or snow, these lightweight boots retain heat and repel water to keep you warmer and drier. Synthetic upper with Thermolite insulation, fleece lining, traction molded TPR rubber sole... more

$49.99

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Blair.com

(475,000+)
Men's Totes Insulated Boots, Black, Size 7

Men's Totes Insulated Boots, Black, Size 7

Shoes by Totes. Comes in Black, Size 7 M. Perfect for rain, sleet or snow, these lightweight boots retain heat and repel water to keep you warmer and drier. Synthetic upper with Thermolite insulation, fleece lining, traction molded TPR rubber sole and... more

$49.99

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Blair.com

(475,000+)
Men's Totes Insulated Boots, Black, Size 11

Men's Totes Insulated Boots, Black, Size 11

Shoes by Totes. Comes in Black, Size 11 M. Perfect for rain, sleet or snow, these lightweight boots retain heat and repel water to keep you warmer and drier. Synthetic upper with Thermolite insulation, fleece lining, traction molded TPR rubber sole and... more

$49.99

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Blair.com

(475,000+)
Carolina Men's 8 Inch Waterproof Insulated Logger Work Boots - Brown, Size 7 Extra Wide, Model CA4821

Carolina Men's 8 Inch Waterproof Insulated Logger Work Boots - Brown, Size 7 Extra Wide, Model CA4821

Tough Carolina 8in. logger work boots feature rugged waterproof Crazy Horse leather uppers for great looks and durability. 100 waterproof/breathable membrane will keep your feet dry and comfortable all day long. Has 600 grams of Thinsulate insulation... more

$144.99

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Men's Twin Gore Pull-On Duck Boot by Haband, Brown, Size 9

Men's Twin Gore Pull-On Duck Boot by Haband, Brown, Size 9

Shoes by Haband. Comes in Brown, Size 9 M. 100% Waterproof Shell, Genuine Leather Upper with wide gore elastic for perfect fit. Thinsulate® Insulated. Anti-Slip Traction Outsole. Defined Heel. *Shipped by the manufacturer. more

$99.99

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English Laundry Easby Chukka Boot (Men) at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

English Laundry Easby Chukka Boot (Men) at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

A suede saddle textures the sides of a streamlined chukka boot shaped from polished leather with a versatile plain toe and traditional two-hole lacing.Sizing: Runs large; order next size down. Round toe. Lace-up style. Grip sole. Approx. 3.5" shaft... more

$185.00 $79.97

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CAMPER' Neuman Leather Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

CAMPER' Neuman Leather Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Whole sizes only; for 1/2 sizes, order next size up. Reference size chart for European conversion. Round toe. Lace-up vamp closure. Reptile embossed leather construction. Removable padded footbed. Approx. 4" shaft height. Grip sole. Imported more

$185.00 $79.97

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H By Hudson Magrey Suede Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

H By Hudson Magrey Suede Chukka Boot at Nordstrom Rack - Mens Shoes - Mens Boots - Mens Chukkas

Whole sizes only; for 1/2 sizes, order next size up. Round toe. Lace-up vamp closure. Topstitched detail. Lightly padded footbed. Grip sole. Approx. 4" shaft height. Imported more

$165.00 $59.97

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Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Walnut-9.5-Medium Model: 387704

Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Walnut-9.5-Medium Model: 387704

Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Walnut-9.5-Medium Model: 387704. 5-Medium more

$185.00

FREE shipping

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Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Dark Shadow-8-Medium Model: 331984

Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Dark Shadow-8-Medium Model: 331984

Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Dark Shadow-8-Medium Model: 331984. Oboz Bridger 8 inch Insulated BDry Hiking Boot - Men's-Dark Shadow-8-Medium more

$185.00

FREE shipping

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Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Walnut-10.5-Medium Model: 387706

Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Walnut-10.5-Medium Model: 387706

Oboz Footwear Bridger 8 Inch Insulated Bdry Hiking Boot - Men's-Walnut-10.5-Medium Model: 387706. 5-Medium more

$185.00

FREE shipping

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Nunn Bush Men's Hatch Plain Toe Chukka Chukka Boot

Nunn Bush Men's Hatch Plain Toe Chukka Chukka Boot

The nunn bush hatch plain toe chukka boot provides a current fashion look that can be worn either in a casual or dress occasion. more

$52.52

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Nunn Bush Men's Hatch Plain Toe Chukka Chukka Boot

Nunn Bush Men's Hatch Plain Toe Chukka Chukka Boot

The nunn bush hatch plain toe chukka boot provides a current fashion look that can be worn either in a casual or dress occasion. more

$93.50

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Rockport Men's Marshall Chukka Chukka Boot, Dark Brown Leather, 11.5 M US

Rockport Men's Marshall Chukka Chukka Boot, Dark Brown Leather, 11.5 M US

Casual friday' isn't just for fridays anymore. smart-yet-relaxed attire has been the standard for years now and the marshall collection is designed to complement that look more

$91.29

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Xray Men's The Windom Casual Chukka Boot 10 Blue Medium

Xray Men's The Windom Casual Chukka Boot 10 Blue Medium

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.98 $34.99

FREE shipping

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Xray Men's The Windom Casual Chukka Boot 7.5 Grey Medium

Xray Men's The Windom Casual Chukka Boot 7.5 Grey Medium

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.98 $34.99

FREE shipping

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Xray Men's The Windom Casual Chukka Boot 12 Blue Medium

Xray Men's The Windom Casual Chukka Boot 12 Blue Medium

Insulated by its incredible looks, the Windom is just right for wearing with just about everything. It pairs well with a plaid and some jeans, and also looks fresh with your favorite suit.Upper: 100% Full suede,Outsole: TPR,Lining: Polyurethane,Heel... more

$74.98 $34.99

FREE shipping

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