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    Bostonian Men's Barbour Boot

    Bostonian Men's Barbour Boot

    Bostonian decorates a plain chukka style with a light burnishing for a smooth finish. more

    $59.99

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    Bostonian Men's Nicky Plain Toe Oxford

    Bostonian Men's Nicky Plain Toe Oxford

    The Bostonian Nicky Plain Toe men's lace-up dress shoe is classic and cozy. This men's chukka has a fine leather upper with a smooth lining, an open cell PU sheet footed, a nylon shank and a fabric sockliner for an extrem comfort and arch support. The... more

    $44.25

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    Bostonian Men's Evanston in Burgundy Leather

    Bostonian Men's Evanston in Burgundy Leather

    It doesn't get any more classic than this handsome men's slip-on shoe. Crafted of premium burgundy leather, it has a sleek profile and is accented with tassel and tooling details. The leather and fabric lining offer all-day comfort, while the leather... more

    $79.99

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    Timberland Earthkeepers City Lite Chukka Men's Lace-up Boots - Brown

    Timberland Earthkeepers City Lite Chukka Men's Lace-up Boots - Brown

    Free Shipping Both Ways! The Earthkeepers City Lite Chukka is the perfect complement to your favorite pair of jeans. Smooth leather upper. Simple two eye lacing. Recycled PET lining wicks moisture and helps control odor. Cushioned footbed is leather... more

    $100.00

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    Zappos.com

    (300,000+)
    Florsheim Jet Chukka Men's Dress Boots - Brown

    Florsheim Jet Chukka Men's Dress Boots - Brown

    Free Shipping Both Ways! Inspired by an Italian demi boot, this handsome dress style is definitely cobbled with a distinguished gentleman in mind. Smooth leather upper with elongated Euro style. Lace-up closure allows for a secure and adjustable fit.... more

    $135.00

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    Zappos.com

    (300,000+)
    Red Wing Heritage Work Chukka Men's Lace-up Boots - Oro-iginal

    Red Wing Heritage Work Chukka Men's Lace-up Boots - Oro-iginal

    Free Shipping Both Ways! Click for Red Wing Heritage® cleaning instructions. Whether working hard or hanging with your friends, you'll look great in the classic Heritage Work Chukka from Red Wing Heritage. Traditional desert boot suede upper with... more

    $260.00

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    Zappos.com

    (300,000+)
    Bostonian Men's Andover in Black Leather

    Bostonian Men's Andover in Black Leather

    With its traditional cap toe, five-eyelet blucher construction and classic leather sole, this elegant dress shoe in black always looks correct. A removable, leather-lined footbed cushions the foot in comfort. more

    $89.99

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    Johnston & Murphy Men's XC-Colorado Chukka - Mahogany, Size 11

    Johnston & Murphy Men's XC-Colorado Chukka - Mahogany, Size 11

    Here's a shoe from Johnston & Murphy's XC (Extreme Comfort) Collection that looks great with everything from khakis to jeans to slacks - in any weather! Rich, full-grain leather uppers sport nicely detailed double stitching with impressive precision.... more

    $165.00

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    Allen Edmonds Bellevue Chukka Boots

    Allen Edmonds Bellevue Chukka Boots

    Allen Edmonds Bellevue Chukka Boots - Allen Edmonds men's shoes are Made-in-the-USA since 1922 of fine imported leathers. We offer men's dress shoes in a variety of sizes, colors, & styles with over 100 size and width variations. With proper care,... more

    $295.00

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    Men's Bostonian Laureate - Black Smooth Leather Loafers

    Men's Bostonian Laureate - Black Smooth Leather Loafers

    The Laureate features a smooth upper, classic design and metallic buckle accent. It has a padded insole for extra comfort. more

    $72.95

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    Shoebuy.com

    (150,000+)
    Vans Alien Workshop Chukka Low Mens Shoes Grey In Sizes 11, 9, 12, 8.5, 13, 10.5, 9.5, 10, 8 For Men 216162115

    Vans Alien Workshop Chukka Low Mens Shoes Grey In Sizes 11, 9, 12, 8.5, 13, 10.5, 9.5, 10, 8 For Men 216162115

    The Chukka Low's collaboration between Alien Workshop and Vans is showcased in the Alien Workshop seasonal colors. These shoes were the result of Vans manufacturing and team rider input. The Chukka Low features Pro Vulc construction, Ultracush HD... more

    $64.99 $49.97

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    (50,000+)
    Bostonian Men's Wenham Black Smooth Leather Shoes, Size 11 M - 25805

    Bostonian Men's Wenham Black Smooth Leather Shoes, Size 11 M - 25805

    Bostonian Men's Wenham Black Smooth Leather Shoes - 25805 more

    $90.00

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    TheShoeMart

    (5,000+)
    Bostonian Men's Bolton Brown Smooth Leather Shoes, Size 15 W - 25896

    Bostonian Men's Bolton Brown Smooth Leather Shoes, Size 15 W - 25896

    Bostonian Men's Bolton Brown Smooth Leather Shoes - 25896 more

    $90.00

    FREE shipping

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    TheShoeMart

    (5,000+)
    Vans Chukka Low Mens Shoes Medium Grey/Deep Sky In Sizes 8.5, 9.5, 10, 12, 10.5, 13, 11, 8, 9 For Men 229472115

    Vans Chukka Low Mens Shoes Medium Grey/Deep Sky In Sizes 8.5, 9.5, 10, 12, 10.5, 13, 11, 8, 9 For Men 229472115

    Vans Chukka Low lace-up deck shoes. Pieced suede and textile upper. Heavily padded tongue and collar. Small Vans side label. Vulcanized rubber midsole. Rubber Vans "Off the Wall" heel badge. Gum rubber waffle outsole. Imported. more

    $64.99 $59.97

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    (50,000+)
    Bostonian Men's Denver in Black/Black Milled

    Bostonian Men's Denver in Black/Black Milled

    Clean, elegant styling in glossy brush-off leather. This classic plain-toe blucher lace-up in black is finished with a stacked heel and features a cushioned footbed and flexible rubber outsole that adds support to each step. more

    $79.99

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    Wenger Men's Alpine Chukka - Brown, Size 7.5

    Wenger Men's Alpine Chukka - Brown, Size 7.5

    Wenger's best Alpine Chukka uses Hydrofoil 3D Waterproof Membrane to seal snow and slush out, while letting body moisture escape. Your feet will stay warm and dry, even in subzero conditions - and even sloshing through slush-clogged parking lots. The... more

    $69.95

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    Men's Bostonian Ipswich - Brown Smooth Leather Oxfords

    Men's Bostonian Ipswich - Brown Smooth Leather Oxfords

    Lightweight and instantly comfortable, this updated blucher lace-up cushions the foot with a padded topline, foam-padded linings, removable footbed and the Flexlite® outsole that combines the performance of an athletic shoe with the look of a dress shoe. more

    $90.00 $79.95

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    Shoebuy.com

    (150,000+)
    Nike Lunar Flyknit Chukka Men's Shoes - Squadron Blue

    Nike Lunar Flyknit Chukka Men's Shoes - Squadron Blue

    The Nike Lunar Flyknit Chukka: Springy cushioning, unique style Built with a patented one-piece weave on top and resilient Lunarlon foam cushioning underfoot, the Nike Lunar Flyknit Chukka Men's Shoe combines a bold look and comfort in a mid-cut... more

    $170.00 $134.97

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    Nike.com

    (2,500+)
    Men's Børn® Boyd Chukka Boots, Dk Brown 10.5M null

    Men's Børn® Boyd Chukka Boots, Dk Brown 10.5M null

    Børn Boyd Chukka Boots - Classic chukka boots from Børn, with textured, full-grain leather upper (Charcoal has suede-leather upper), and leather lining. Opanka construction ensures superior comfort, flexibility and durability. Steel shank provides... more

    $140.00

    FREE shipping

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    Allen Edmonds Chukkamok Chukka Boots

    Allen Edmonds Chukkamok Chukka Boots

    Lace-up oxford casual bootsLong wingtip chukka bootsUnstructured leather upperRough CollectionRubber sole360 degree Goodyear welt234 LastRecraftableMade in USA more

    $157.00

    FREE shipping

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