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    Mens Dress Chukka Boots

    1-21 of 21 results
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    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    New!
    Sale
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Dark Bitter Chocolate 2 Suede
    New
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Black
    Rockport Total Motion Fusion Desert Boot(
Men's) -
New Dress Blues
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Rocksand
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Tan
    $149.95
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    New!
    Sale
    Stacy Adams Delaney Chukka Boot 25053(
Men's) -
Black Burnished Leather/Suede
    New
    Stacy Adams Delaney Chukka Boot 25053(
Men's) -
Brown Burnished Leather/Suede
    New
    Stacy Adams Delaney Chukka Boot 25053(
Men's) -
Cognac Burnished Leather/Suede
    New
    $104.95
    Clarks Holmby Top Chukka Boot (Men's)
    Clarks Holmby Top Chukka Boot (Men's)
    Clarks Holmby Top Chukka Boot (Men's)
    New!
    Sale
    Clarks Holmby Top Chukka Boot(
Men's) -
Black Goat Full Grain Leather
    New
    Clarks Holmby Top Chukka Boot(
Men's) -
Brown Goat Full Grain Leather
    New
    $99.95
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(
Men's) -
Coffee Lexi Leather
    ECCO Turn GORE-TEX Boot(
Men's) -
Mocha Oil Nubuck
    Sale
    $172.95 - $229.95
    $230.00 up to 25% off
    Nunn Bush Robinson Chukka Boot (Men's)
    Nunn Bush Robinson Chukka Boot (Men's)
    Nunn Bush Robinson Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Robinson Chukka Boot(
Men's) -
Black Leather
    Sale
    Nunn Bush Robinson Chukka Boot(
Men's) -
Chestnut Leather
    Sale
    $72.00
    $90.00 20% off
    Andrew Marc Dorchester Chukka (Men's)
    Andrew Marc Dorchester Chukka (Men's)
    New!
    Sale
    Andrew Marc Dorchester Chukka(
Men's) -
Caribou/Black/Dark Natural/Natural Suede
    Sale
    $89.00
    $178.00 50% off
    Dockers Merritt Chukka Boot (Men's)
    Dockers Merritt Chukka Boot (Men's)
    Dockers Merritt Chukka Boot (Men's)
    Dockers Merritt Chukka Boot (Men's)
    New!
    Sale
    Dockers Merritt Chukka Boot(
Men's) -
Black Milled Leather
    Sale
    Dockers Merritt Chukka Boot(
Men's) -
Chocolate Crazy Horse Leather
    Sale
    Dockers Merritt Chukka Boot(
Men's) -
Dark Tan Crazy Horse Leather
    Sale
    $79.99
    $110.00 27% off
    Nunn Bush Hawley Chukka Boot (Men's)
    Nunn Bush Hawley Chukka Boot (Men's)
    Nunn Bush Hawley Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Hawley Chukka Boot(
Men's) -
Black Leather
    Sale
    Nunn Bush Hawley Chukka Boot(
Men's) -
Brown Leather
    Sale
    $72.00
    $90.00 20% off
    Dockers Longden Chukka Boot (Men's)
    Dockers Longden Chukka Boot (Men's)
    Dockers Longden Chukka Boot (Men's)
    Dockers Longden Chukka Boot (Men's)
    New!
    Sale
    Dockers Longden Chukka Boot(
Men's) -
Black Burnished Full Grain Leather
    Sale
    Dockers Longden Chukka Boot(
Men's) -
Red Brown Burnished Full Grain Leather
    Sale
    Dockers Longden Chukka Boot(
Men's) -
Taupe Suede
    Sale
    $79.99
    $110.00 27% off
    Clarks Un.Elott Mid Chukka Boot (Men's)
    Clarks Un.Elott Mid Chukka Boot (Men's)
    Clarks Un.Elott Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Un.Elott Mid Chukka Boot(
Men's) -
Black Cow Full Grain Leather
    New
    Clarks Un.Elott Mid Chukka Boot(
Men's) -
Burgundy Cow Full Grain Leather
    New
    $179.95
    Caterpillar Sutter Ankle Boot (Men's)
    Caterpillar Sutter Ankle Boot (Men's)
    Caterpillar Sutter Ankle Boot (Men's)
    Caterpillar Sutter Ankle Boot (Men's)
    New!
    Sale
    Caterpillar Sutter Ankle Boot(
Men's) -
Black Full Grain Leather
    New
    Caterpillar Sutter Ankle Boot(
Men's) -
Burgundy Full Grain Leather
    New
    Caterpillar Sutter Ankle Boot(
Men's) -
Rust Full Grain Leather
    New
    $209.99
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    Timberland Newport Bay Chukka Boot (Men's)
    Description:
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    The Timberland Earthkeepers Britton Hill Chukka is an environmentally friendly twist on a classic favorite. The eco-friendly, Silver-rated-tannery-produced premium leather ...
    Timberland Earthkeepers Britton Hill Chukka Boot (Men's)
    Description:
    The Timberland Earthkeepers Britton Hill Chukka is an environmentally friendly twist on a classic favorite. The eco-friendly, Silver-rated-tannery-produced premium leather upper features perforations and contrast stitch detailing. Breathable mesh lining is made from 100% PET from recycled plastic bottles. 100% ...
    The slim, fashion-forward chukka silhouette of the Galen satisfies the dapper gentleman's need for smart design and comfort. This 3 ...
    UGG Galen Chukka Boot (Men's)
    Description:
    The slim, fashion-forward chukka silhouette of the Galen satisfies the dapper gentleman's need for smart design and comfort. This 3 eyelet chukka boot features distressed suede detail on the heel counter and pull tab. Insole: Dual density leather lined foam ...