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    Steve Madden 'Bronxxx' Chukka Boot (Men)

    Steve Madden 'Bronxxx' Chukka Boot (Men)

    Shop the Anniversary Sale + Free Shipping!

    High-shine leather shapes a sleek chukka boot with cool vintage style. Color(s): tan leather. Brand: Steve Madden. Style Name: Steve Madden 'Bronxxx' Chukka Boot (Men). Style Number: 682860_1. Manufacturer part number BRONXXX Leather upper/synthetic... more

    $125.00 $79.90

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    Nordstrom

    (1,000+)
    Roper Mens Vintage Nubuck Ankle Boots

    Roper Mens Vintage Nubuck Ankle Boots

    Vintage leather Fabric linings Removable EVA insoles Stirrup friendly rubber outsole EVA molded midsole for comfort Two eyelet chukka more

    $99.95

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    (5,000+)
    Vintage Shoe Company Derek: Men's Chukka

    Vintage Shoe Company Derek: Men's Chukka

    Chukkas: Vintage Shoe Company Derek - Male Adult - Sage Suede (Green) - Sizes 8|8.5|9.5|10|10.5|11|11.5|12|13 - Widths: Medium - Prowl the urban jungle in the timeless, handsome style of the Vintage Shoe Company Derek boot, proudly made in the U.S.A.... more

    $234.95

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    OnlineShoes.com

    (50,000+)
    Vintage Shoe Company Derek: Men's Chukka

    Vintage Shoe Company Derek: Men's Chukka

    Chukkas: Vintage Shoe Company Derek - Male Adult - Chocolate Harness (Brown) - Sizes 8|9|9.5|10|10.5|13 - Widths: Medium - Prowl the urban jungle in the timeless, handsome style of the Vintage Shoe Company Derek boot, proudly made in the U.S.A.... more

    $234.95

    FREE shipping

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    OnlineShoes.com

    (50,000+)
    Vintage Shoe Company Derek: Men's Chukka

    Vintage Shoe Company Derek: Men's Chukka

    Chukkas: Vintage Shoe Company Derek - Male Adult - Cork Suede (Tan) - Sizes 8|8.5|9|9.5|10|10.5|11|11.5|12|13 - Widths: Medium - Prowl the urban jungle in the timeless, handsome style of the Vintage Shoe Company Derek boot, proudly made in the U.S.A.... more

    $234.95

    FREE shipping

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    OnlineShoes.com

    (50,000+)
    Frye James Chukka Men's Lace-up Boots - Dark Brown Soft Vintage Leather

    Frye James Chukka Men's Lace-up Boots - Dark Brown Soft Vintage Leather

    Free Shipping Both Ways! It's time to take a breath. The next jump is going to be into a world of style and prestige with the James Chukka by Frye. Antiqued leather upper material. Lace-up closure for a secure and snug fit. Comfortable, leather-lined... more

    $268.00

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    Zappos.com

    (300,000+)
    Frye James Crepe Chukka Men's Lace-up Boots - Cognac Soft Vintage Leather

    Frye James Crepe Chukka Men's Lace-up Boots - Cognac Soft Vintage Leather

    Free Shipping Both Ways! Take that leap into something amazing with the Frye James Crepe Chukka boot. Antiqued leather upper material. Lace-up closure for a secure and snug fit. Comfortable, leather-lined interior. Cushioned leather footbed. Crepe... more

    $258.00

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    Zappos.com

    (300,000+)
    Frye Phillip Chukka Men's Lace-up Boots - Cognac Soft Vintage Leather

    Frye Phillip Chukka Men's Lace-up Boots - Cognac Soft Vintage Leather

    Free Shipping Both Ways! The Phillip Chukka offers the perfect amount of sophistication that can be dressed up or down. Soft vintage leather upper. Lace closure. Smooth leather lining. Cushioned leather insole. Durable leather outsole. Imported.... more

    $278.00

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    Zappos.com

    (300,000+)
    Men's Marc New York by Andrew Marc Hudson - Lead/Light Grey Suede Boots

    Men's Marc New York by Andrew Marc Hudson - Lead/Light Grey Suede Boots

    The vintage-inspired Hudson boot delivers a smart look that can be dressed up or down. This classic ankle high chukka boot has a soft suede upper, stitchdown construction and a durable rubber sole. more

    $127.99 $100.00

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    Shoebuy.com

    (150,000+)
    John Varvatos Dylan Laceless Chukka Boots - Leather (For Men) ? DARK BROWN

    John Varvatos Dylan Laceless Chukka Boots - Leather (For Men) ? DARK BROWN

    CLOSEOUTS . A waxed and hand-burnished leather upper gives John Varvatos Dylan laceless chukka boots a refined vintage appearance that pairs well with jeans or trousers for a worn, sophisticated look. Available Colors: BLACK, DARK BROWN. Sizes: 7, 7.5,... more

    $413.60 $229.95

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    (700,000+)
    Creative Recreation Vito Mens Shoes Olive In Sizes 8.5, 11, 9.5, 13, 10, 12, 8, 9, 10.5 For Men 230444531

    Creative Recreation Vito Mens Shoes Olive In Sizes 8.5, 11, 9.5, 13, 10, 12, 8, 9, 10.5 For Men 230444531

    Creative Recreation's Vito is an updated version of the classic chukka--a smart necessity in any man's closet. slub chambray with brown suede accents and merry mesh lining. Suede tongue label with debossed logo. Vintage cupsole construction. Rubber... more

    $79.99

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    (50,000+)
    John Varvatos Dylan Laceless Chukka Boots - Leather (For Men) ? BLACK

    John Varvatos Dylan Laceless Chukka Boots - Leather (For Men) ? BLACK

    CLOSEOUTS . A waxed and hand-burnished leather upper gives John Varvatos Dylan laceless chukka boots a refined vintage appearance that pairs well with jeans or trousers for a worn, sophisticated look. Available Colors: BLACK, DARK BROWN. Sizes: 7, 7.5,... more

    $413.60 $229.95

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    (700,000+)
    Men's Danner Tramline Marquam - Black Full Grain Leather Boots

    Men's Danner Tramline Marquam - Black Full Grain Leather Boots

    The Tramline Marquam brings easy wearing chukka style to Danner's original mountain boot aesthetic. Hand-crafted in Portland, OR, this boot features Armortred outsoles and all around great styling. Leather lined for a vintage look and feel, with... more

    $309.95

    FREE shipping

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    Shoebuy.com

    (150,000+)
    Clarks Originals 'Desert' Boot (Men)

    Clarks Originals 'Desert' Boot (Men)

    Shop the Anniversary Sale + Free Shipping!

    Crepe outsole provides added cushioning and comfort for a vintage-style chukka boot. Color(s): beeswax. Brand: Clarks Originals. Style Name: Clarks Originals 'Desert' Boot (Men). Style Number: S04840_30. Manufacturer part number 78358 Suede upper and... more

    $120.00

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    Nordstrom

    (1,000+)
    Clarks Originals 'Desert' Chukka Boot (Men)

    Clarks Originals 'Desert' Chukka Boot (Men)

    Shop the Anniversary Sale + Free Shipping!

    Crepe outsole provides added cushioning and comfort for a vintage-style chukka boot. Color(s): sand nubuck/ green sole, taupe nubuck orange sole. Brand: Clarks Originals. Style Name: Clarks Originals 'Desert' Chukka Boot (Men). Style Number: 625225.... more

    $120.00

    FREE shipping

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    Nordstrom

    (1,000+)
    Pikolinos Glasgow 05M-6030F Men's Lace-up Boots

    Pikolinos Glasgow 05M-6030F Men's Lace-up Boots

    Free Shipping on all orders! Add a Euro-inspired look with vintage appeal to your everyday wear with the Glasgow 05M-6030F chukka from Pikolinos®. Premium leather upper with contrast stitching and a traditional lacing system for easy on-and-off wear... more

    $200.00 $109.99

    FREE shipping

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    6pm.com

    (25,000+)
    Lloyd Nash Men's Lace-up Boots

    Lloyd Nash Men's Lace-up Boots

    Free Shipping on all orders! A fun update on the classic chukka silhouette, these Lloyd® shoes are sure to be your go-to look for every day wear. Supple suede upper with vintage-inspired brogue detailing and contrast stitching. Lace-up design allows... more

    $249.00 $111.99

    FREE shipping

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    6pm.com

    (25,000+)
    Marc New York Marc New York Hudson Suede Boots-Green-Size 13

    Marc New York Marc New York Hudson Suede Boots-Green-Size 13

    The vintage-inspired Hudson boot delivers a smart look that can be dressed up or down. This classic ankle high chukka boot has a soft suede upper, stitchdown construction and a durable rubber sole. more

    $69.99

    FREE shipping

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    Overstock.com

    (600,000+)
    Mens Andrew Marc Greenwich Espresso/black/deep Natural Leather

    Mens Andrew Marc Greenwich Espresso/black/deep Natural Leather

    Designed for the modern man, the vintage inspired Greenwich boot adds a casual sophistication to the wardrobe. This chukka boot features a semi-nubuck leather upper, leather and cotton drill interior lining, stitchdown construction more

    $130.00

    FREE shipping

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    Overstock.com

    (600,000+)
    Marc New York Hudson Suede Boots

    Marc New York Hudson Suede Boots

    The vintage-inspired Hudson boot delivers a smart look that can be dressed up or down. This classic ankle high chukka boot has a soft suede upper, stitchdown construction and a durable rubber sole. more

    $69.99

    FREE shipping

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    Overstock.com

    (600,000+)

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