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Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,11 W US

Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,11 W US

Chukka inspired boot featuring Hydro Shield waterproof leather upper with four pairs of blind eyelets, lightly padded collar, and gusseted tongue EVA footbed conforms to foot for personalized fit Adiprene shock absorbing cushioning TPR outsole absorbs... more

$99.00

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Rockport Men's Northfield WP Plain Toe Chukka Boot- Chocolate Waterproof-11.5 XW

Rockport Men's Northfield WP Plain Toe Chukka Boot- Chocolate Waterproof-11.5 XW

Comfort system designed to provide lightweight shock absorption. Hydro-shield construction offers waterproof leather, a seam sealed, waterproof insole, and a gusseted tongue to help keep feet dry Ethylene vinyl acetate outsole provides lightweight... more

$84.95

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Best Seller
Rockport Men's Essential Details Waterproof Dress Chukka Boot, Black, 15 M US

Rockport Men's Essential Details Waterproof Dress Chukka Boot, Black, 15 M US

Chukka inspired boot featuring Hydro Shield waterproof leather upper with four pairs of blind eyelets, lightly padded collar, and gusseted tongue EVA footbed conforms to foot for personalized fit Adiprene shock absorbing cushioning TPR outsole absorbs... more

$109.95

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Skechers USA Men's Sergeants Verdict Chukka Boot,Black Waterproof Oiled Smooth Leather,8 M US

Skechers USA Men's Sergeants Verdict Chukka Boot,Black Waterproof Oiled Smooth Leather,8 M US

Waterproof Smooth fabric shoe lining more

$63.92

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UGG Men's Neumel Waterproof Chukka Boot, Charcoal, 05 M US

UGG Men's Neumel Waterproof Chukka Boot, Charcoal, 05 M US

Waterproof leather upper Waterproof and seam sealed construction Tread lite by UGG outsole to provide maximum cushioning and traction UGGpure wool lining and insole Includes two sets of laces more

$179.95

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Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Black, 8 M US

Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Black, 8 M US

Rebound cushioning provides lasting comfort Constructed with 3mm Neo-Tech waterproof insulation DuraFresh organic bio-technology activates to fight odors BioGrip slip resistant outsole Bogs Max-Wick moves sweat away from your foot to keep you dry more

$61.70

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Columbia Men's Irvington II Chukka Leather Waterproof Boot, Cordovan, Pebble, 7.5 Regular US

Columbia Men's Irvington II Chukka Leather Waterproof Boot, Cordovan, Pebble, 7.5 Regular US

Solid non-marking rubber outsole Techlite lightweight cushioned midsole Full grain leather with metal eyelets. Wool collar lining. Waterproof seam sealed construction. more

$106.36

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UGG Men's HARKLEY Waterproof Chukka Boot, desert tan, 17 Medium US

UGG Men's HARKLEY Waterproof Chukka Boot, desert tan, 17 Medium US

Waterproof and seam-sealed leather upper UGGpure wool lining Treadlite by UGG outsole for cushion, comfort and traction UGGpure wool insole Seam sealed construction more

$94.98

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UGG Men's Neumel Waterproof Chukka Boot, black, 11 Medium US

UGG Men's Neumel Waterproof Chukka Boot, black, 11 Medium US

Waterproof and seam-sealed leather upper UGGpure wool lining Treadlite by UGG outsole for cushion, comfort and traction Cushioning foam insole lined with UGGpure wool 4.25 Inches shaft height more

$179.95

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Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Dark Brown, 14 M

Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Dark Brown, 14 M

Rebound cushioning provides lasting comfort Constructed with 3mm Neo-Tech waterproof insulation DuraFresh organic bio-technology activates to fight odors BioGrip slip resistant outsole Bogs Max-Wick moves sweat away from your foot to keep you dry more

$68.92

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Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Dark Brown, 10 M

Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Dark Brown, 10 M

Rebound cushioning provides lasting comfort Constructed with 3mm Neo-Tech waterproof insulation DuraFresh organic bio-technology activates to fight odors BioGrip slip resistant outsole Bogs Max-Wick moves sweat away from your foot to keep you dry more

$69.95

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Steve Madden Men's Cove Waterproof Chukka Boot, Brown Suede, 13 M US

Steve Madden Men's Cove Waterproof Chukka Boot, Brown Suede, 13 M US

Waterproof Men's suede chukka boot Steve Madden Men's more

$109.95

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Timberland Men's Mt. Maddsen Waterproof Chukka Boot, Dark Brown Full Grain, 090W W US

Timberland Men's Mt. Maddsen Waterproof Chukka Boot, Dark Brown Full Grain, 090W W US

Upper made with premium waterproof leather from an LWG Silver-rated tannery Timber Dry waterproof membrane Fully gusseted tongue Removable anti-fatigue foot bed Compression-molded EVA midsole more

$119.95

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UGG Men's Neumel Waterproof Chukka Boot, Chestnut, 10 M US

UGG Men's Neumel Waterproof Chukka Boot, Chestnut, 10 M US

Waterproof full-grain leather upper 17mm UGGpure wool lining Treadlite by UGG outsole Fully waterproof and seam-sealed construction Cushioning foam insole lined with 17mm UGGpure wool more

$179.95

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Timberland Men's Mt. Maddsen Waterproof Chukka Boot, Dark Brown Full Grain, 095W W US

Timberland Men's Mt. Maddsen Waterproof Chukka Boot, Dark Brown Full Grain, 095W W US

Upper made with premium waterproof leather from an LWG Silver-rated tannery Timber Dry waterproof membrane Fully gusseted tongue Removable anti-fatigue foot bed Compression-molded EVA midsole more

$119.95

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Timberland Mens Mt. Maddsen Waterproof Chukka Boot, Black Full Grain, 9W US

Timberland Mens Mt. Maddsen Waterproof Chukka Boot, Black Full Grain, 9W US

Upper made with premium waterproof leather from an LWG Silver-rated tannery Timber Dry waterproof membrane Fully gusseted tongue Removable anti-fatigue foot bed Compression-molded EVA midsole more

$119.95

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Caterpillar Men's Parameter Waterproof Chukka Boot Black 10.5 M US

Caterpillar Men's Parameter Waterproof Chukka Boot Black 10.5 M US

Full grain leather upper delivers long-term durability and protection High cushion foam FlexFWD footbed mixed with cork and rebound foam top layer is flexible, durable and LIGHTWEIGHT Waterproof feature keeps water out and feet dry Soft, breathable... more

$124.95

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UGG Men's UNION CHUKKA WATERPROOF Boot, Stout, 10.5 M US

UGG Men's UNION CHUKKA WATERPROOF Boot, Stout, 10.5 M US

Waterproof leather upper Combination treadlite by UGG and rubber outsole Fully waterproof and seam-sealed construction UGG dynamic support platform shank for proper foot flex Flexfit bootie more

$149.95

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Chaco Men's Frontier Waterproof Chukka Boot, Mocha, 8 M US

Chaco Men's Frontier Waterproof Chukka Boot, Mocha, 8 M US

Waterproof and salt- repelling Snowplow Leather upper Seam- sealed, waterproof construction Suede padded collar for added comfort Metal hook and lacing eyelet for secure lacing Waxed cotton laces Non- marking Chaco Grip full rubber block outsole Skid-... more

$79.29

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Chaco Men's Frontier Waterproof Chukka Boot, Mocha, 11.5 M US

Chaco Men's Frontier Waterproof Chukka Boot, Mocha, 11.5 M US

Waterproof and salt- repelling Snowplow Leather upper Seam- sealed, waterproof construction Suede padded collar for added comfort Metal hook and lacing eyelet for secure lacing Waxed cotton laces Non- marking Chaco Grip full rubber block outsole Skid-... more

$110.69

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Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Java Nubuck Wp, 8.5 M US

Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Java Nubuck Wp, 8.5 M US

Classic dress chukka lace boot Waterproof Leather covered mold footbed for additional comfort more

$110.61

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Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Midnight Nubuck wp, 7 M US

Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Midnight Nubuck wp, 7 M US

Classic dress chukka lace boot Waterproof Leather covered mold footbed for additional comfort more

$214.73

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Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Java Nubuck Wp, 8.5 W US

Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Java Nubuck Wp, 8.5 W US

Classic dress chukka lace boot Waterproof Leather covered mold foot bed for additional comfort more

$228.89

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Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Midnight Nubuck wp, 8.5 M US

Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Midnight Nubuck wp, 8.5 M US

Classic dress chukka lace boot Waterproof Leather covered mold footbed for additional comfort more

$214.73

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Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Java Nubuck Wp, 7.5 M US

Cole Haan Men's Wagner Grand Apron Chukka Waterproof Boot, Java Nubuck Wp, 7.5 M US

Classic dress chukka lace boot Waterproof Leather covered mold footbed for additional comfort more

$214.73

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Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,12 M US

Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,12 M US

Chukka inspired boot featuring Hydro Shield waterproof leather upper with four pairs of blind eyelets, lightly padded collar, and gusseted tongue Sponge EVA footbed Adiprene shock absorbing cushioning TPR outsole absorbs shock and reduces foot fatigue more

$105.00

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Skechers Men's Sergeants Verdict Chukka Boot,Black Waterproof Oiled Smooth Leather,13 M US

Skechers Men's Sergeants Verdict Chukka Boot,Black Waterproof Oiled Smooth Leather,13 M US

Waterproof Smooth fabric shoe lining more

$63.92

FREE shipping

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Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Dark Green, 13 M US

Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Dark Green, 13 M US

100% Waterproof Rebound cushioning in footbed for lasting comfort DuraFresh bio-technology that activates to fight unwanted odors Footbed lined with Bogs Max-Wick to keep feet dry Non-marking BioGrip slip resistant outsole more

$76.99

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Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Black, 12 M US

Bogs Men's Sauvie Slip On Low Height Chukka Waterproof Rain Boot, Black, 12 M US

Rebound cushioning provides lasting comfort Constructed with 3mm Neo-Tech waterproof insulation Durafresh organic bio-technology activates to fight odors Biogrip slip resistant outsole Bogs Max-Wick moves sweat away from your foot to keep you dry more

$67.57

FREE shipping

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Columbia Men's Irvington II Chukka Leather Waterproof Boot, Cordovan, Pebble, 8 Regular US

Columbia Men's Irvington II Chukka Leather Waterproof Boot, Cordovan, Pebble, 8 Regular US

Solid non-marking rubber outsole Techlite lightweight cushioned midsole Full grain leather with metal eyelets. Wool collar lining. Waterproof seam sealed construction. more

$114.45

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UGG Men's Neumel Waterproof Chukka Boot, black, 12 Medium US

UGG Men's Neumel Waterproof Chukka Boot, black, 12 Medium US

Waterproof and seam-sealed leather upper UGGpure wool lining Treadlite by UGG outsole for cushion, comfort and traction Cushioning foam insole lined with UGGpure wool more

$179.95

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UGG Men's HARKLEY Waterproof Chukka Boot, Desert tan, 18 Medium US

UGG Men's HARKLEY Waterproof Chukka Boot, Desert tan, 18 Medium US

Waterproof and seam-sealed leather upper UGGpure wool lining Treadlite by UGG outsole for cushion, comfort and traction UGGpure wool insole Seam sealed construction more

$94.98

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UGG Men's HARKLEY WATERPROOF Chukka Boot, desert tan, 15 Medium US

UGG Men's HARKLEY WATERPROOF Chukka Boot, desert tan, 15 Medium US

Waterproof and seam-sealed leather upper UGGpure wool lining Treadlite by UGG outsole for cushion, comfort and traction UGGpure wool insole Seam sealed construction more

$190.00

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Nunn Bush Men's Nantucket Waterproof Cap Toe Chukka Boot Lace-Up, Black, 8 W US

Nunn Bush Men's Nantucket Waterproof Cap Toe Chukka Boot Lace-Up, Black, 8 W US

STYLE: The Nantucket Waterproof Classic Cap Toe Chukka Boot features classic and timeless styling. Perfect for casual and dress occasions especially when inclement weather calls for waterproof footwear COMFORT: Our proprietary Comfort Gel full length... more

$59.95

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Nunn Bush Men's Nantucket Waterproof Cap Toe Chukka Boot Lace-Up, Black, 9.5

Nunn Bush Men's Nantucket Waterproof Cap Toe Chukka Boot Lace-Up, Black, 9.5

STYLE: The Nantucket Waterproof Classic Cap Toe Chukka Boot features classic and timeless styling. Perfect for casual and dress occasions especially when inclement weather calls for waterproof footwear COMFORT: Our proprietary Comfort Gel full length... more

$59.95

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UGG Men's Freamon Waterproof Chukka Boot, chestnut, 7 Medium US

UGG Men's Freamon Waterproof Chukka Boot, chestnut, 7 Medium US

Chukka boot energy comfort insole with built-in arch support Treadlite by UGG outsole Waterproof suede and nubuck upper more

$139.95

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Timberland Men's Mt. Maddsen Waterproof Chukka Boot, Dark Brown Full Grain, 075M M US

Timberland Men's Mt. Maddsen Waterproof Chukka Boot, Dark Brown Full Grain, 075M M US

Upper made with premium waterproof leather from an LWG Silver-rated tannery Timber Dry waterproof membrane Fully gusseted tongue Removable anti-fatigue foot bed Compression-molded EVA midsole more

$117.68

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UGG Men's HARKLEY Waterproof Chukka Boot, Black TNL, 8 M US

UGG Men's HARKLEY Waterproof Chukka Boot, Black TNL, 8 M US

Waterproof full-grain leather upper 17mm UGGpure wool lining Treadlite by UGG outsole Fully waterproof and seam-sealed construction Cushioning foam insole lined with 17mm UGGpure wool more

$179.95

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UGG Men's HARKLEY Waterproof Chukka Boot, Black TNL, 12 M US

UGG Men's HARKLEY Waterproof Chukka Boot, Black TNL, 12 M US

Waterproof full-grain leather upper 17mm UGGpure wool lining Treadlite by UGG outsole Fully waterproof and seam-sealed construction Cushioning foam insole lined with 17mm UGGpure wool more

$179.95

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Caterpillar Men's Parameter Waterproof Chukka Boot, Dark Cafe, 7.5 M US

Caterpillar Men's Parameter Waterproof Chukka Boot, Dark Cafe, 7.5 M US

Full grain leather upper delivers long-term durability and protection High cushion foam FlexFWD footbed mixed with cork and rebound foam top layer is flexible, durable and LIGHTWEIGHT Waterproof feature keeps water out and feet dry Soft, breathable... more

$124.95

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