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    Timberland rightfully has earned a rock-solid reputation for boots, shoes and other premium products with a refined sense of rugged. Pioneers in the...

    Timberland

    Timberland Mens Chukka Boots

    1-22 of 22 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)
    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
    Timberland Earthkeepers Brook Park Chukka(
Men's) -
Red Brown Smooth
    Sale
    $104.95 - $129.95
    $130.00 up to 19% off
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    New!
    Sale
    Timberland Grantly Chukka Boot(
Men's) -
Black Full Grain Leather/Suede
    Timberland Grantly Chukka Boot(
Men's) -
Brown Full Grain Leather/Suede
    Timberland Grantly Chukka Boot(
Men's) -
Dark Brown Full Grain Leather/Suede
    $139.95
    Timberland Groveton Leather and Fabric Chukka Boot (Men's)
    Timberland Groveton Leather and Fabric Chukka Boot (Men's)
    Timberland Groveton Leather and Fabric Chukka Boot (Men's)
    Timberland Groveton Leather and Fabric Chukka Boot (Men's)
    Timberland Groveton Leather and Fabric Chukka Boot (Men's)
    Timberland Groveton Leather and Fabric Chukka Boot (Men's)
    New!
    Sale
    Timberland Groveton Leather and Fabric Chukka Boot(
Men's) -
Black Iris Monochromatic Nubuck
    New
    Timberland Groveton Leather and Fabric Chukka Boot(
Men's) -
Black Tech Tuff Dual Original Full Grain Leather
    New
    Timberland Groveton Leather and Fabric Chukka Boot(
Men's) -
Chili Pepper Monochromatic Nubuck
    New
    Timberland Groveton Leather and Fabric Chukka Boot(
Men's) -
New Gourd Monochromatic Nubuck
    New
    Timberland Groveton Leather and Fabric Chukka Boot(
Men's) -
Wheat Nubuck/Canvas
    $79.95
    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
    Timberland Britton Hill Waterproof Chukka Boot (Men's)
    Timberland Britton Hill Waterproof Chukka Boot (Men's)
    Timberland Britton Hill Waterproof Chukka Boot (Men's)
    New!
    Sale
    Timberland Britton Hill Waterproof Chukka Boot(
Men's) -
Black Quartz with Buttersoft
    Sale
    Timberland Britton Hill Waterproof Chukka Boot(
Men's) -
Chestnut Quartz with Buttersoft
    Sale
    $140.95
    $180.00 22% 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
    Timberland Groveton Moc Toe Chukka (Men's)
    Timberland Groveton Moc Toe Chukka (Men's)
    Timberland Groveton Moc Toe Chukka (Men's)
    Timberland Groveton Moc Toe Chukka (Men's)
    New!
    Sale
    Timberland Groveton Moc Toe Chukka(
Men's) -
Black Tech Tuff Dual Original Full Grain Leather
    New
    Timberland Groveton Moc Toe Chukka(
Men's) -
Blackout Nubuck
    Timberland Groveton Moc Toe Chukka(
Men's) -
Wheat Nubuck
    $99.95
    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
    Related Products
    Slip into this classic lace-up smooth leather chukka boot featuring lightweight and comfort construction. Crafted with bold stitch detailing, a ...
    Flexi Fabiano Chukka Boot 69802 (Men's)
    Description:
    Slip into this classic lace-up smooth leather chukka boot featuring lightweight and comfort construction. Crafted with bold stitch detailing, a fully-padded footbed, and a low heel. This style has a flexible crepe and non-slip outsole. Additional Info Slip-Resistant (Non-Skid) , ...
    Classic construction contributes to a nostalgic sensibility in the Steve Madden Harken chukka boot. Genuine leather upper with contrast stitching ...
    Steve Madden Harken Chukka Boot (Men's)
    Description:
    Classic construction contributes to a nostalgic sensibility in the Steve Madden Harken chukka boot. Genuine leather upper with contrast stitching and lace-up front. Select styles features a fabric quarter section. Textile liner and man-made sole. Leather upper Lace-up front Fabric ...
    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 ...