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    Pikolinos Mens Cork 07S-6811 Chukka Boot

    Pikolinos Mens Cork 07S-6811 Chukka Boot

    Let the skies become your limit with the new Pikolinos Cork 6811. Handsome, light and durable, the new Pikolinos Cork 6811 is sure to take you to the edge of the world with complete style and ease. Thanks to its padded footbed that provides underfoot... more

    $209.95

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    Pikolinos Men's Chile 5056 Chukka Boots

    Pikolinos Men's Chile 5056 Chukka Boots

    Be ruggedly stylish and comfortable with the Pikolinos Chile Chukka 5056 boot. This men's casual lace-up boot features a full grain leather upper with sporty, hiking-inspired lace-up styling and a sidewalk-worthy latex rubber sole for traction. The... more

    $165.00

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    Pikolinos Men's 05M-6030F Ankle Boot

    Pikolinos Men's 05M-6030F Ankle Boot

    The Pikolinos Glasgow 6030F men's lace-up chukka is on a mission to make a smooth fashion anoucement! This men's ankle boot is set in a fine leather upper with a round toe. A cushioned footbed, a smooth lining and a synthetic outsole lend durability,... more

    $139.95

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    Pikolinos Men's Glasgow Chukka Boot

    Pikolinos Men's Glasgow Chukka Boot

    Premium leather upper with contrast stitching and a traditional lacing system for easy on-and-off wear and a secure fit. Soft leather interior lining ensures an abrasion-free environment for all-day wear. Fully cushioned footbed massages the foot with... more

    $150.00

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

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

    Free Shipping Both Ways! 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 and a... more

    $200.00

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    Zappos.com

    (300,000+)
    Pikolinos Glasgow 05M-6030F Men's Lace-up Boots

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

    Free Shipping Both Ways! 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 and a... more

    $200.00

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    Zappos.com

    (300,000+)
    Alden Men's Chukka Boot Shell Cordovan Black Shell Boots, Size 10.5 D - 1340

    Alden Men's Chukka Boot Shell Cordovan Black Shell Boots, Size 10.5 D - 1340

    Alden Men's Chukka Boot Shell Cordovan Black Shell Boots - 1340 more

    $710.00

    FREE shipping

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    TheShoeMart

    (5,000+)
    Allen Edmonds Gobi Chukka Boots

    Allen Edmonds Gobi Chukka Boots

    Lace-up oxford casual bootsPlain-toe chukka bootsLined suede or leather upperRubber sole360 degree Goodyear welt809 LastRecraftableMade in USA more

    $177.00

    FREE shipping

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    Ahnu Harris Chukka Boots - Leather (For Men) – PORTER

    Ahnu Harris Chukka Boots - Leather (For Men) – PORTER

    Get 25% off $75 or 30% off $100 with PCZILLAUS5

    CLOSEOUTS . With a cushioned dual-density insole and genuine leather upper, Ahnu Harris chukka boots give you handsome style and long-lasting comfort. Available Colors: BLACK, OLIVE NIGHT, PORTER. Sizes: 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13. more

    $135.00 $63.71

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    (725,000+)
    Clarks Senner Drive Leather Chukka Boots (For Men) – CHOCOLATE

    Clarks Senner Drive Leather Chukka Boots (For Men) – CHOCOLATE

    Get 25% off $75 or 30% off $100 with PCZILLAUS5

    CLOSEOUTS . Clarks Senner Drive chukka boots bring fresh appeal to a traditional look with smart stitching details and toe overlays on tumbled, full-grain leather. Available Colors: CHOCOLATE. Sizes: 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13. more

    $100.00 $69.95

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    (725,000+)
    Men's Danner St. Helens 4" Chukka - Brown/Red Boots

    Men's Danner St. Helens 4" Chukka - Brown/Red Boots

    This shoe features a durable, waterproof nubuck leather and suede upper with lightweight woven nylon and a Danner Double Hook system for customizable secure fit. It has a 100% waterproof and breathable GORE-TEX® membrane with an extended comfort... more

    $149.95

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    Shoebuy.com

    (150,000+)
    Hugo Boss Sorreno | Suede Chukka Boot

    Hugo Boss Sorreno | Suede Chukka Boot

    Calfskin suede leather 2-hole lacing Oval toe Contrast topstitching at the quarter and heelLeather lining and sole more

    $315.00 $157.99

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    Allen Edmonds Bellevue Chukka Boots

    Allen Edmonds Bellevue Chukka Boots

    Lace-up oxford casual bootsPlain-toe chukka bootLined leather upperRubber sole360 degree Goodyear welt511 LastRecraftableMade in USA more

    $295.00

    FREE shipping

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    Georgia Boot GB1222 Barracuda Gold Chukka Wedge Boot

    Georgia Boot GB1222 Barracuda Gold Chukka Wedge Boot

    Cleaning out the stalls, hauling hay and distributing food to livestock is extremely hard work. To help you accomplish the daily tasks on the farm, you should consider wearing these Georgia Farm & Ranch Chukka Work Boots.These Chukka boots have been... more

    $114.99

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    Alden Men's Unlined Chukka Boot Flex Welt Suede Dark Brown Suede Boots, Size 9.5 D - 1492

    Alden Men's Unlined Chukka Boot Flex Welt Suede Dark Brown Suede Boots, Size 9.5 D - 1492

    Alden Men's Unlined Chukka Boot Flex Welt Suede Dark Brown Suede Boots - 1492 more

    $520.00

    FREE shipping

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    TheShoeMart

    (5,000+)
    Blackstone DM49 Suede Sport Chukka Boots (For Men) – TAUPE

    Blackstone DM49 Suede Sport Chukka Boots (For Men) – TAUPE

    Get 25% off $75 or 30% off $100 with PCZILLAUS5

    CLOSEOUTS . Blackstone s DM49 suede sport chukka boots are trying to decide whether they re a boot or a sneaker. It s not a desperate sort of identity crisis, because either way this slouchy, low-riding shoe is going to rock your casuals. In... more

    $169.00 $38.03

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    (725,000+)
    Cole Haan Men's Camden Chukka Steel Grey Boots, Size 10 M - C14136

    Cole Haan Men's Camden Chukka Steel Grey Boots, Size 10 M - C14136

    Cole Haan Men's Camden Chukka Steel Grey Boots - C14136 more

    $177.95

    FREE shipping

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    TheShoeMart

    (5,000+)
    Clarks Originals Men's Desert Trek Chukka Boot

    Clarks Originals Men's Desert Trek Chukka Boot

    Men's Clarks Desert Trek Shoes for retro style! Clarks introduced the Desert Trek about 30 years ago... and it's never looked better! Though folks will definitely take notice of the cool 2-eye, ankle-high design... they're more than just good-lookin'... more

    $57.18

    FREE shipping

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    Men's Timberland Baluster Chukka - Dark Brown Smooth Boots

    Men's Timberland Baluster Chukka - Dark Brown Smooth Boots

    This chukka boot has a leather upper, a moisture wicking textile lining, a Smart Comfort® chassis, and a rubber outsole. more

    $94.95

    FREE shipping

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    Shoebuy.com

    (150,000+)
    Harford Chukka Boot by Joseph Abboud JoS. A. Bank

    Harford Chukka Boot by Joseph Abboud JoS. A. Bank

    Save 0.22%!

    Chukka boot in soft suede uppers by Joseph Abboud features genuine suede leather uppers with leather linings and a cushioned footbed with full rubber outsoles for long lasting comfort. 100% leather. Imported. Spot clean. Harford Chukka Boot by Joseph... more

    $165.00 $129.00

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    Timberland Men's Baluster Chukka

    Timberland Men's Baluster Chukka

    The Timberland 54568 boots feature a leather upper with a moc toe. The man-made outsole lends lasting traction and wear. more

    $79.95

    FREE shipping

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    Men's Corbin Chukka Boot

    Men's Corbin Chukka Boot

    Find comfort, quality and style in the Corbin Boot. It features a durable upper, laces for good fit, mesh lining, Dexter's signature Comfort Insole for all-day support, and a textured outsole. Manmade materials. more

    $59.99 $44.99

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    Men's Mark Nason Skechers Elmwood - Black Boots

    Men's Mark Nason Skechers Elmwood - Black Boots

    Stylish and handsome meets comfort in the Mark Nason SKECHERS Elmwood boot. Smooth premium leather upper in a lace up low ankle height dress casual chukka boot with stitching accents and Memory Foam insole. Stitching accents. Rounded plain toe front.... more

    $123.95

    FREE shipping

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    Shoebuy.com

    (150,000+)
    Tommy Bahama Relaxology Rivington Suede Chukka Boot

    Tommy Bahama Relaxology Rivington Suede Chukka Boot

    Tommy Bahama Relaxology Rivington Suede Chukka Boot give you a relaxed, comfortable, lightweight feel. Theri design gives you support and shock absorption and strobel construction for greater strength and flexibility. more

    $91.08

    FREE shipping

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    Men's Corbin Chukka Boot

    Men's Corbin Chukka Boot

    Find comfort, quality and style in the Corbin Boot. It features a durable upper, laces for good fit, mesh lining, Dexter's signature Comfort Insole for all-day support, and a textured outsole. Manmade materials. more

    $59.99 $44.99

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    Hugo Boss Urdon | Leather Chukka Boot

    Hugo Boss Urdon | Leather Chukka Boot

    Naturally grained semi-lustrous finishTooling at quarters and heel counters4-hole lace-up vamp Round toeUnlined100% buffalo leather more

    $345.00

    FREE shipping

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    Hugo Boss Sorreno | Suede Chukka Boot

    Hugo Boss Sorreno | Suede Chukka Boot

    Calfskin suede leather 2-hole lacing Oval toe Contrast topstitching at the quarter and heelLeather lining and sole more

    $315.00 $157.99

    FREE shipping

    go to store
    Allen Edmonds Bellevue Chukka Boots

    Allen Edmonds Bellevue Chukka Boots

    Lace-up oxford casual bootsPlain-toe chukka bootLined leather upperRubber sole360 degree Goodyear welt511 LastRecraftableMade in USA more

    $295.00

    FREE shipping

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    Men's Corbin Chukka Boot

    Men's Corbin Chukka Boot

    Find comfort, quality and style in the Corbin Boot. It features a durable upper, laces for good fit, mesh lining, Dexter's signature Comfort Insole for all-day support, and a textured outsole. Manmade materials. more

    $59.99 $44.99

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    Justin Sport Chukka Boots

    Justin Sport Chukka Boots

    Sporty style for the weekend & beyond.. Rugged leather uppers. Easy-wearing cushion insoles. Lace-up shafts give a better fit. Rubber soles for extra traction when you need it. Vendor Style: 988. Take Justin on the trail, or across town - wherever your... more

    $159.99

    FREE shipping

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    Reebok Chukka Work Boots - USPS Approved

    Reebok Chukka Work Boots - USPS Approved

    Made with genuine leather. MIL-33 moisture-wicking lining. Removable PI-1000 cushion insert. 100% non-metallic - Airport safe!. USPS approved. Maxum-Lite slip and oil-resistant polyurethane sole. Vendor Style: CP8500. Reeboks chukka boot is a solid... more

    $178.99

    FREE shipping

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    Timberland Oakwell Moc Toe Chukka - Mens - Wheat

    Timberland Oakwell Moc Toe Chukka - Mens - Wheat

    Wheat size 7.0

    Don't let cold and wet conditions keep you from showcasing your style, trust the Timberland Oakwell Moc Toe Chukka boots to keep you in prime condition all season long. Premium nubuck leather upper for comfort, durability, and long-lasting wear. 100%... more

    $109.99 $59.99

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    Foot Locker

    (175,000+)
    Frye Mens Walter Chukka Shoes

    Frye Mens Walter Chukka Shoes

    This expertly crafted chukka boot is made from rich smooth full grain leather that has been hand oiled and burnished. Bench crafted in the USA.Smooth Full Grain leather upper. Leathe lined. Leather outsole. Goodyear welt construction. Made in USA. Size... more

    $378.00

    FREE shipping

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    Bass Plano Chukka Boots Men's Shoes

    Bass Plano Chukka Boots Men's Shoes

    Bass Plano Chukka Boots Men's Shoes Shoes MEN Complete casual outfits with these classic suede chukka boots from Bass. more

    $89.00

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    Rockport Casual Plain-Toe Path to Greatness Chukka Boots Men's Shoes

    Rockport Casual Plain-Toe Path to Greatness Chukka Boots Men's Shoes

    Rockport Casual Plain-Toe Path to Greatness Chukka Boots Men's Shoes Shoes MEN The chukka from Rockport is back and better than ever with more comfort features. Crafted in richly colored suede to pair with everything from chinos to jeans. more

    $115.00 $85.99

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    Timberland Earth Keepers Ryker Mens Dark Brown Waterproof Leather Chukka Boots

    Timberland Earth Keepers Ryker Mens Dark Brown Waterproof Leather Chukka Boots

    5 5.5 6 6.5 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13 5 5.5 6 6.5 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 12.5 13 14 15 16 17 18 19 20 0 1 2 3 4 5 6 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 12.5 13 13.5 1 1.5 2 2.5 3 3.5 4 4.5 5 5.5 6 more

    $147.89

    FREE shipping

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    Johnston And Murphy Kholson Chukka Mens Black Or Mohogany Leather Casual Boots

    Johnston And Murphy Kholson Chukka Mens Black Or Mohogany Leather Casual Boots

    5 5.5 6 6.5 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13 5 5.5 6 6.5 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 12.5 13 14 15 16 17 18 19 20 0 1 2 3 4 5 6 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 12.5 13 13.5 1 1.5 2 2.5 3 3.5 4 more

    $66.15

    FREE shipping

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    $505 Italy Dsquared2 Suede-leather Chukka-boot High-top Sneakers 43-it 10-us

    $505 Italy Dsquared2 Suede-leather Chukka-boot High-top Sneakers 43-it 10-us

    Italy DSQUARED2 Suede-Leather Chukka-Boot High-Top Sneakers Italian Soft Suede Leather. Fully Leather Lined Interior.Made In Italy.Retails For Over $500 USD. Brand New w/ Original Box Men's Size: 43-IT / 10-USA Outsole Measurements: Outsole Bottom... more

    $136.91

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    Men's Kennebec Casual Chukka Boots 11 W(Ee) Gray

    Men's Kennebec Casual Chukka Boots 11 W(Ee) Gray

    Designed to feel like your favorite pair of sneakers, this lightweight boot is the evolution of dress casual. Boasting a perfect combination of classic style and sporty comfort, it is the only boot you'll want to wear whether you're in the workplace or... more

    $99.00 $89.99

    FREE shipping

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    (2,500+)
    Men's Kennebec Casual Chukka Boots, Leather 10.5 M(D) Brown

    Men's Kennebec Casual Chukka Boots, Leather 10.5 M(D) Brown

    Designed to feel like your favorite pair of sneakers, this lightweight boot is the evolution of dress casual. Boasting a perfect combination of classic style and sporty comfort, it is the only boot you'll want to wear whether you're in the workplace or... more

    $109.00

    FREE shipping

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    (2,500+)

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