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    Wide Mens Chukka Boots

    1-34 of 34 results
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    Timberland Earthkeepers Brook Park Chukka (Men's)
    Timberland Earthkeepers Brook Park Chukka (Men's)
    Timberland Earthkeepers Brook Park Chukka (Men's)
    New!
    Sale
    Timberland Earthkeepers Brook Park Chukka(
Men's) -
Black Smooth
    Timberland Earthkeepers Brook Park Chukka(
Men's) -
Brown Smooth
    $104.95 - $129.95
    $130.00 up to 19% off
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(
Men's) -
Beeswax Leather
    Sale
    $84.95
    $99.00 14% off
    Nunn Bush Rawson Chukka (Men's)
    Nunn Bush Rawson Chukka (Men's)
    Nunn Bush Rawson Chukka (Men's)
    New!
    Sale
    Nunn Bush Rawson Chukka(
Men's) -
Black Leather
    Sale
    Nunn Bush Rawson Chukka(
Men's) -
Chestnut Leather
    Sale
    $71.95
    $90.00 20% off
    Rockport Charson Lace Up Ankle Boot (Men's)
    Rockport Charson Lace Up Ankle Boot (Men's)
    New!
    Sale
    Rockport Charson Lace Up Ankle Boot(
Men's) -
Dark Brown Leather
    Sale
    $109.95 - $139.95
    $140.00 up to 21% off
    Rockport Sharp & Ready Charson Boot (Men's)
    Rockport Sharp & Ready Charson Boot (Men's)
    New!
    Sale
    Rockport Sharp & Ready Charson Boot(
Men's) -
Dark Bitter Chocolate/Brick Suede
    Sale
    $103.95 - $139.95
    $140.00 up to 26% off
    Timberland Premium Chukka (Men's)
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(
Men's) -
Wheat Nubuck
    Sale
    $134.95
    $145.00 7% off
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    New!
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Black Suede Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Brown Suede Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Chestnut Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Navy Suede
    Sale
    $67.45
    $100.00 33% 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
    Timberland Earthkeepers City Lite Waterproof Chukka (Men's)
    Timberland Earthkeepers City Lite Waterproof Chukka (Men's)
    Timberland Earthkeepers City Lite Waterproof Chukka (Men's)
    New!
    Sale
    Timberland Earthkeepers City Lite Waterproof Chukka(
Men's) -
Black Smooth Leather
    Sale
    Timberland Earthkeepers City Lite Waterproof Chukka(
Men's) -
Brown Oiled Nubuck
    Sale
    $94.95
    $120.00 21% off
    Clarks Newkirk Top (Men's)
    Clarks Newkirk Top (Men's)
    Clarks Newkirk Top (Men's)
    New!
    Sale
    Clarks Newkirk Top(
Men's) -
Black Leather
    Clarks Newkirk Top(
Men's) -
Dark Brown Nubuck
    $134.95
    Drew Keith (Men's)
    Drew Keith (Men's)
    Drew Keith (Men's)
    New!
    Sale
    Drew Keith(
Men's) -
Black Leather
    Drew Keith(
Men's) -
Brandy Leather
    $179.95
    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
    Caterpillar Parker Steel Toe Chukka Boot (Men's)
    Caterpillar Parker Steel Toe Chukka Boot (Men's)
    Caterpillar Parker Steel Toe Chukka Boot (Men's)
    Caterpillar Parker Steel Toe Chukka Boot (Men's)
    New!
    Sale
    Caterpillar Parker Steel Toe Chukka Boot(
Men's) -
Black Full Grain Leather
    New
    Caterpillar Parker Steel Toe Chukka Boot(
Men's) -
Dark Beige Full Grain Leather
    New
    Caterpillar Parker Steel Toe Chukka Boot(
Men's) -
Honey Reset Full Grain Leather
    New
    $129.95
    Timberland Classic TBLŪ Chukka (Men's)
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(
Men's) -
Wheat Nubuck Leather
    Sale
    $109.95
    $135.00 19% off
    Hush Puppies Roland Jester Chukka Boot (Men's)
    Hush Puppies Roland Jester Chukka Boot (Men's)
    Hush Puppies Roland Jester Chukka Boot (Men's)
    Hush Puppies Roland Jester Chukka Boot (Men's)
    Hush Puppies Roland Jester Chukka Boot (Men's)
    Hush Puppies Roland Jester Chukka Boot (Men's)
    New!
    Sale
    Hush Puppies Roland Jester Chukka Boot(
Men's) -
Dark Brown Leather
    New
    Hush Puppies Roland Jester Chukka Boot(
Men's) -
Dark Grey Suede
    New
    Hush Puppies Roland Jester Chukka Boot(
Men's) -
Cashew Leather
    Hush Puppies Roland Jester Chukka Boot(
Men's) -
Midnight Leather
    New
    Hush Puppies Roland Jester Chukka Boot(
Men's) -
Navy Suede
    New
    $138.95
    Caterpillar Parker Chukka Boot (Men's)
    Caterpillar Parker Chukka Boot (Men's)
    Caterpillar Parker Chukka Boot (Men's)
    Caterpillar Parker Chukka Boot (Men's)
    New!
    Sale
    Caterpillar Parker Chukka Boot(
Men's) -
Black Full Grain Leather
    New
    Caterpillar Parker Chukka Boot(
Men's) -
Dark Beige Full Grain Leather
    New
    Caterpillar Parker Chukka Boot(
Men's) -
Honey Reset Full Grain Leather
    New
    $124.95
    Related Products
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    Frye Luke Wingtip Chukka (Men's)
    Description:
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    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 ...
    Combining preppy, casual style with rugged sensibility, the Dorchester Chukka SE boasts a soft quilted peacoat with a slightly burnished ...
    Andrew Marc Dorchester Chukka SE (Men's)
    Description:
    Combining preppy, casual style with rugged sensibility, the Dorchester Chukka SE boasts a soft quilted peacoat with a slightly burnished heel and toe. This lace-up boot features a leather midsole, stitchdown construction and rubber sole with wooden heel inserts. Additional ...