Men's Brunello Cucinelli Suede ChukkaBoot - Brown - Casual boots Clean lines and minimal detailing keep things casual and relaxed in a chukkaboot that sets brushed Italian suede on a bright rubber sole. Lace-up style Leather upper and lining/rubber... more
Men's ugg(r) Neumel Water Resistant High Top ChukkaBoot - Black - Casual boots Supple suede wraps a cozy, adventure-ready chukkaboot updated with a high-top inspired silhouette and durable Treadlite sole. The cushy fit is enhanced with UGGplush... more
Men's Clarks(r) Torhill Hi ChukkaBoot - Brown - Casual boots Creamy suede and soft sheepskin lining enrich a handsome boot in a classic silhouette with a chunky rubber sole. more
Men's To Boot New York Richard ChukkaBoot - Brown - Casual boots Soft suede adds a laid-back vintage-inspired touch to this dapper Italian-made chukkaboot built on a sturdy leather sole featuring grippy rubber tread. Leather upper and lining/rubber... more
Men's Bruno Magli Taddeo Leather ChukkaBoots - Black - Casual boots Bruno Magli "Taddeo" chukkaboots in soft Italian calf leather 1.25 in / 30 mm stacked heel Round toe Laceup vamp Branded tongue and pull tab Boot shaft, approx. 6.0"H Rubber outsole... more
Men's Sorel Madson Ii Waterproof ChukkaBoot - Brown - Casual boots Combining a chukka silhouette with rugged performance and durability, this waterproof boot is an easy choice for your everyday adventures. more
Rocky Boots Tmc Postal-approved Public Service ChukkaBoots - FQ0005005BK7W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For The... more
These Deer Stags® Bangor ChukkaBoots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more
Men's Blake McKay Dixon ChukkaBoot - Brown - Casual boots Premium suede lends old-world charm to this water-repellent Chukkaboot with breathable linings and a cushy antimicrobial insole for all-day comfort. more
Men's Blake McKay Toby ChukkaBoot - Brown - Casual boots Natural rubber crepe soles cushion every step you take in these versatile chukkaboots that develop more interesting character with wear. Leather upper and lining/rubber sole Made in Brazil. more
Men's Dockers Dartford ChukkaBoot - Brown - Casual boots Your casual style gets a sophisticated touch with the Dartford chukkaboot from Dockers. With its Supreme Comfort massaging footbed, moisture-wicking sock cover and a fabric lining, this boot... more
Men's Crosby Square Thorne ChukkaBoot - Brown - Casual boots A rear pull-tab lends easy entry to a supple suede chukkaboot grounded by a cushioned footbed and flexible crepe sole. Lace-up style Cushioned footbed with arch support Leather upper and... more
Men's Warfield & Grand Arlington ChukkaBoot - Brown - Casual boots Burnished Italian calfskin enriches a classic chukkaboot built with cushioned arch support for superior comfort. more
Rocky Boots Tmc Postal-approved Public Service ChukkaBoots - FQ0005005BK85W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more
Rocky Boots Tmc Postal-approved Public Service ChukkaBoots - FQ0005005BK8W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For The... more
Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank and... more
Men's Blake McKay Colton ChukkaBoot - Brown - Casual boots Contrast stitching highlights the classic silhouette of a smooth leather chukkaboot grounded by a cushioned, arch-supporting OrthoLite® footbed. more
Men's Clarks(r) Corston Db Waterproof ChukkaBoot - Brown - Casual boots This sleek Chukkaboot is ready for all weather conditions with it's waterproof upper and cozy faux-shearling lining. The textured rubber sole provides excellent traction on... more
Men's Anthony Veer Bushwick ChukkaBoot - Brown - Casual boots Accent a casual look with the sharp Bushwick chukkaboot from Anthony Veer. This suede pair sports an OrthoLite footbed for added cushioning. Suede upper. Lace-up closure. Round toe.... more
Men's Nunn Bush Otto Plain Toe ChukkaBoot - Black - Casual boots The classic design of the Otto plain toe chukkaboot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more
Men's Stacy Adams Tilden ChukkaBoot - Blue - Casual boots You can only up your dapper quo pairing the Tilden chukkaboot by Stacy Adams with your outfit. This suede boot is highlighted with contrast welt and stitching details for a stylish look.... more
Rocky Boots Tmc Postal-approved Public Service ChukkaBoots - FQ0005005BK8M. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For The... more
Rocky Boots Tmc Postal-approved Public Service ChukkaBoots - FQ0005005BK10M. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more
Men's Thomas & Vine Aldridge ChukkaBoot - Brown - Casual boots The Aldridge chukkaboot from Thomas & Vine is an essential footwear for casual occasions. This lace-up shoe includes an embossed suede heel for added flair and a second pair of contrast... more
Men's Gordon Rush Austin ChukkaBoot - Black - Casual boots Elevate your work-to-weekend look in this refined Italian-leather chukkaboot featuring Blake stitch construction, breathable lining and an Ortho Lite® insole. more
Men's Ron White Larrado Weatherproof ChukkaBoot - Black - Casual boots A leather upper and soft flannel collar add modern elements to a sophisticated chukkaboot grounded by a cushioned footbed and durable lug sole. Multilayered, PORON®-cushioned... more
Men's Clarks(r) Wallabee ChukkaBoot - Brown - Casual boots A classic crepe-rubber sole grounds a chunky leather chukkaboot complete with a smartly stitched toe. more
Men's Sandro Moscoloni Shawn ChukkaBoot - Blue - Casual boots The Shawn chukkaboot from Sandro Moscoloni proves a versatile must-have with a classic design to finish off favorite fits. This leather pair's cushioned footbed adds a comfortable layer.... more
Men's Barbour Reverb ChukkaBoot - Brown - Casual boots The brand's iconic tartan makes a discreet appearance at the pull-tab of a streamlined chukkaboot crafted from buttery-smooth, matte-finish nubuck leather. Lace-up style Removable, cushioned... more
Men's Taft Livingston ChukkaBoot - Black - Casual boots Keep your look distinguished with the Livingston chukkaboot from Taft. A wingtip toe with brogue accentuation creates a tasteful look to the leather and wool boot, made cozy with a cushioned... more
Men's Sperry Top-Sider Cold Bay Chukka Duck Boot - Brown - Casual boots Take on chilly days in the Sperry Cold Bay Chukka duck boot. The cushioned details and rubber sole with Wave-SipingTM combine for a comfortable and secure addition to your... more
Men's Steve Madden Manoa ChukkaBoot - Brown - Casual boots With a classic design and a leather construction, the Manoa chukkaboot from Steve Madden is an easy add to your everyday looks. The versatile option features a simple silhouette, complete... more
Men's Santoni Rock ChukkaBoot - Brown - Casual boots Burnished suede lends handsome appeal to a laceless chukkaboot set on a robust lug sole. Leather upper and lining/rubber sole Made in Italy. more
Men's Propet Kenton ChukkaBoot - Brown - Casual boots The Kenton chukkaboot by Propet upgrades your off-duty style. DuroCloudTM foam embedded midsole provides supreme cushioning, while high density Open Cell foam at the insole ensures superior air... more
Men's Karl Lagerfeld Side Zip Leather ChukkaBoots - Brown - Casual boots Karl Lagerfeld Paris chukkaboots in box leather 1.25 in / 30 mm stacked heel Round toe Laceup vamp Side zip eases on and off Pulltab at backstay Embossed metal ring at backstay... more
Men's Allen Edmonds Chandler ChukkaBoot - Brown - Casual boots Premium, finely napped suede elevates a classic chukkaboot handcrafted with a comfortable cork insole, durable bench welt and rubber grip sole. 360o welt construction for durability and... more
Men's Blake McKay Alder ChukkaBoot - Brown - Casual boots Crafted from rich, breathable leather and durable rubber, this flexible chukkaboot is a wardrobe workhorse that's sure to be on heavy rotation all year long. The antimicrobial insole means a... more
Men's Steve Madden Harken ChukkaBoot - Black - Casual boots Boasting a classic look ready to pair with favorite formal or professional looks, the Harken chukkaboot is sure to please. The contrast stitching makes for an eye-catching statement, while... more
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