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    Discount Mens Casual Chukka Boots

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    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(Men's) -Beeswax Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Brown Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Grey Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Greystone Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Navy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Wheat Suede
    Sale
    $64.99 - $89.99
    $100.00 up to 35% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Black/Black Leather
    Sale
    Clarks Desert Boot(Men's) -Mahogany Suede
    Sale
    Clarks Desert Boot(Men's) -Navy Canvas
    Sale
    Clarks Desert Boot(Men's) -Taupe Canvas
    Sale
    $68.99 - $139.95
    $130.00 - $140.00 up to 51% off
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's) -Black/Black Leather
    Sale
    $104.99 - $140.00
    $140.00 up to 25% off
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
    Sale
    Clarks Wallabee(Men's) -Black/Black Leather
    Sale
    $135.00
    $135.00 - $160.00 up to 16% off
    Nunn Bush Lancaster Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Black Oiled Leather
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Brown Oiled Leather
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Camel Suede
    Sale
    $55.95
    $80.00 30% off
    Clarks Broyd Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Broyd Mid Chukka Boot(Men's) -Black Leather
    Sale
    Clarks Broyd Mid Chukka Boot(Men's) -Tan Leather
    Sale
    $128.99
    $140.00 8% off
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Tan Leather
    Sale
    $76.99 - $99.95
    $100.00 - $110.00 up to 30% off
    Florsheim Montinaro Chukka Boot (Men's)
    New!
    Sale
    Florsheim Montinaro Chukka Boot(Men's) -Saddle Tan Smooth Leather
    Sale
    Florsheim Montinaro Chukka Boot(Men's) -Black Smooth Leather
    Sale
    $99.95
    $109.95 9% off
    UGG Freamon Waterproof Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    UGG Freamon Waterproof Chukka Boot(Men's) -Grizzly Full Grain Leather
    Sale
    $112.95
    $150.00 25% off
    G.H. Bass & Co. Bennett Chukka (Men's)
    New!
    Sale
    G.H. Bass & Co. Bennett Chukka(Men's) -Black Tumbled Leather
    Sale
    G.H. Bass & Co. Bennett Chukka(Men's) -Brown Crazy Horse Leather
    Sale
    $89.99 - $99.99
    $110.00 - $135.00 up to 26% off
    Timberland Killington Chukka Boot (Men's)
    New!
    Sale
    Timberland Killington Chukka Boot(Men's) -Navy Full Grain Leather/Mesh
    Sale
    Timberland Killington Chukka Boot(Men's) -Navy Leather
    Sale
    $74.95 - $124.95
    $125.00 up to 40% off
    Wolverine Bedford Soft Toe Chukka Boot (Men's)
    New!
    Sale
    Wolverine Bedford Soft Toe Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    Wolverine Bedford Soft Toe Chukka Boot(Men's) -Brown Full Grain Leather
    Sale
    $88.99
    $115.00 23% off
    Clarks Stratton Limit Boot (Men's)
    New!
    Sale
    Clarks Stratton Limit Boot(Men's) -Brown Leather
    Sale
    $101.25 - $134.95
    $135.00 up to 25% off
    Cole Haan Williams Welt Chukka II (Men's)
    New!
    Sale
    Cole Haan Williams Welt Chukka II(Men's) -Chestnut Burnish Leather/Suede
    Sale
    Cole Haan Williams Welt Chukka II(Men's) -Driftwood/Driftwood Suede
    Sale
    $139.95
    $250.00 44% off
    Rockport Charson Lace Up Ankle Boot (Men's)
    New!
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Black Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
    Sale
    $98.45
    $110.00 10% off
    UGG Leighton Waterproof Chukka Boot (Men's)
    New!
    Sale
    UGG Leighton Waterproof Chukka Boot(Men's) -Chestnut Suede
    Sale
    $127.95
    $170.00 25% off
    Rockport Wynstin Chukka Boot (Men's)
    New!
    Sale
    Rockport Wynstin Chukka Boot(Men's) -Dark Bitter Chocolate Leather
    Sale
    $110.46 - $130.00
    $130.00 up to 15% off
    Lugz Mantle Mid Chukka Work Boot (Men's)
    New!
    Sale
    Lugz Mantle Mid Chukka Work Boot(Men's) -Black Synthetic
    Sale
    Lugz Mantle Mid Chukka Work Boot(Men's) -Golden Wheat/Tan-Khaki/Gum Synthetic
    Sale
    $43.99
    $54.99 20% off
    Clarks Atticus Limit Chukka Boot (Men's)
    New!
    Sale
    Clarks Atticus Limit Chukka Boot(Men's) -Navy Nubuck
    Sale
    Clarks Atticus Limit Chukka Boot(Men's) -Taupe Nubuck
    Sale
    $107.99 - $134.95
    $135.00 up to 20% off
    Wolverine Bedford Steel Toe Chukka Boot (Men's)
    New!
    Sale
    Wolverine Bedford Steel Toe Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    Wolverine Bedford Steel Toe Chukka Boot(Men's) -Brown Full Grain Leather
    Sale
    $92.99
    $120.00 23% off
    Cole Haan Pinch Weekender Chukka (Men's)
    New!
    Sale
    Cole Haan Pinch Weekender Chukka(Men's) -Black Suede
    Sale
    Cole Haan Pinch Weekender Chukka(Men's) -Navy Ink Suede
    Sale
    Cole Haan Pinch Weekender Chukka(Men's) -Woodbury Suede
    Sale
    $69.95 - $98.95
    $150.00 up to 53% off
    UGG Freamon Hyperweave Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Black Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Marino Textile
    Sale
    $81.95 - $89.95
    $150.00 up to 45% off
    Cole Haan Original Grand Chukka (Men's)
    New!
    Sale
    Cole Haan Original Grand Chukka(Men's) -Black Rubber
    Sale
    Cole Haan Original Grand Chukka(Men's) -Dark Roast/Cobblestone Leather
    Sale
    $125.95
    $180.00 30% off
    Dansko Jake Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Dansko Jake Plain Toe Chukka Boot(Men's) -Black Antiqued Calf
    Sale
    Dansko Jake Plain Toe Chukka Boot(Men's) -Taupe Milled Nubuck
    Sale
    $129.95
    $194.95 33% off
    Deer Stags Seattle Boot (Men's)
    New!
    Sale
    Deer Stags Seattle Boot(Men's) -Black
    Sale
    Deer Stags Seattle Boot(Men's) -Luggage
    Sale
    $59.99
    $80.00 25% off
    Rockport Classic Break Chukka Boot (Men's)
    New!
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
    Sale
    $106.45
    $120.00 11% off
    Florsheim Navigator Chukka Boot (Men's)
    New!
    Sale
    Florsheim Navigator Chukka Boot(Men's) -Cocoa Nubuck
    Sale
    $89.95
    $120.00 25% off
    Steve Madden Herrin Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Herrin Chukka Boot(Men's) -Tan Leather
    Sale
    $63.00 - $89.95
    $90.00 up to 30% off
    Altra Footwear Smith Chukka Boot (Men's)
    New!
    Sale
    Altra Footwear Smith Chukka Boot(Men's) -Blue/Lime
    Sale
    $83.95
    $120.00 30% off
    Drew Keith (Men's)
    New!
    Sale
    Drew Keith(Men's) -Black Leather
    Sale
    Drew Keith(Men's) -Brandy Leather
    Sale
    $149.95 - $169.95
    $190.00 up to 21% off
    ECCO Turn GORE-TEX Chukka Tie Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Black Cow Oil Nubuck
    Sale
    $195.50
    $230.00 15% off
    Cole Haan GrandPro Chukka Sneaker (Men's)
    New!
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Black Leather
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Black Oiled Velour Suede
    Sale
    $97.50 - $112.95
    $150.00 up to 35% off
    Dockers Tulane Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Dockers Tulane Plain Toe Chukka Boot(Men's) -Black Oily Tumbled Full Grain
    Sale
    Dockers Tulane Plain Toe Chukka Boot(Men's) -Chocolate Oily Tumbled Full Grain
    Sale
    Dockers Tulane Plain Toe Chukka Boot(Men's) -Dark Tan Burnished Crazyhorse
    Sale
    $69.99
    $90.00 22% off