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    Rockport City Smart - Waterproof Dress Chukka Boot Men's Boots

    Rockport City Smart - Waterproof Dress Chukka Boot Men's Boots

    Free Shipping Both Ways! Your commute to work should be a breeze, let the City Smart - H20 Dress Chukka Boot keep your feet dry and comfortable. Made with premium seam sealed Hydro-Shield® waterproof leather to keep your feet dry during wet conditions.... more

    $150.00

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    Zappos.com

    (300,000+)
    Rockport Essential Details Waterproof Dress Chukka Men's Lace-up Boots

    Rockport Essential Details Waterproof Dress Chukka Men's Lace-up Boots

    Free Shipping Both Ways! To the office and beyond, make sure you've got the look that's perfect for everyday with the Rockport® Essential Details Waterproof Dress Chukka. Premium leather upper with Hydro-Shield® waterproofing substances tanned into the... more

    $110.00

    FREE shipping

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    Zappos.com

    (300,000+)
    Cole Haan Lionel Dress Boot Men's Dress Lace-up Boots

    Cole Haan Lionel Dress Boot Men's Dress Lace-up Boots

    Free Shipping Both Ways! Look your best every time you put on these excellent Cole Haan shoes. Smooth leather upper with tonal stitching. Pull loop at heel. Lace up front closure with blind eyelets. Perforated toe detail. Leather lining and insole.... more

    $348.00

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    Zappos.com

    (300,000+)
    Men's Florsheim Duke - Cavello Kid Cognac Boots

    Men's Florsheim Duke - Cavello Kid Cognac Boots

    Part of Florsheim's Core Collection, footwear in an array of styles from classic to contemporary, for men who recognize and appreciate quality. Florsheim dress boots are coming back and riding high on the fashion best-sellers list. Bicycle front with... more

    $134.95

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    (150,000+)
    Men's Nunn Bush Bristol - Black Boots

    Men's Nunn Bush Bristol - Black Boots

    Men's dress boots that never go out of style. Smooth, genuine leather upper with a leather sole. Side zipper for easy-on and -off. more

    $80.00 $64.00

    FREE shipping

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    (150,000+)
    Florsheim Welter Boot Men's Dress Zip Boots

    Florsheim Welter Boot Men's Dress Zip Boots

    Free Shipping on all orders! Give your outfit sleek flair with the tailored look of the Welter Boot. Smooth, premium leather upper with topstitched overlay. Side zipper and back pull tab for easy on and off and twin goring for flexible comfort.... more

    $110.00 $77.99

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    EXPRESS Mens Black Leather Chukka Boot

    EXPRESS Mens Black Leather Chukka Boot

    . Named After A Period Of Play In Polo, Chukkas Do Overtime In Comfort And Style. Minimalist Lacing Sits Well Under Jeans And Dress Pants, Allowing The Smooth Leather Upper To Stand Out. A Herringbone Wool Footbed Adds Some Class To This Popular Pick.... more

    $138.00

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    Florsheim Vantage Chukka Boots - Leather (For Men) ? BROWN TUMBLED

    Florsheim Vantage Chukka Boots - Leather (For Men) ? BROWN TUMBLED

    Get 30% off $100 or more with PCZILLAUS5

    CLOSEOUTS . Men who prefer boots to shoes in casual and dress venues will embrace the comfort and polished good looks of Florsheim's Vantage chukka boots. Not only is the top line softly padded, but the Comfortechnology interior absorbs shock, supports... more

    $135.00 $94.95

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    (700,000+)
    UGG Leighton Men's Dress Lace-up Boots

    UGG Leighton Men's Dress Lace-up Boots

    Free Shipping on all orders! Find effortless luxury with the fit-in-anywhere Leighton desert boot from UGG® Australia. Rich oiled full-grain leather or suede upper in an easy lace-up silhouette for a secure fit. Soft leather lining wicks away moisture... more

    $160.00 $104.99

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    EXPRESS Mens Brown Leather Chukka Boot

    EXPRESS Mens Brown Leather Chukka Boot

    . Named After A Period Of Play In Polo, Chukkas Do Overtime In Comfort And Style. Minimalist Lacing Sits Well Under Jeans And Dress Pants, Allowing The Smooth Leather Upper To Stand Out. A Herringbone Wool Footbed Adds Some Class To This Popular Pick.... more

    $138.00

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    Giorgio Brutini Men's 80575 Dress Boot,Black,13 M

    Giorgio Brutini Men's 80575 Dress Boot,Black,13 M

    Giorgio Brutini is an enduring name that evokes fashion and quality. The supple leathers, the hand finished detailing and the superior quality materials are all hallmarks of this established brand. more

    $50.58

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    Bass Men's Amsterdam Ankle Boot,Black,11.5 M US

    Bass Men's Amsterdam Ankle Boot,Black,11.5 M US

    The Amsterdam dress shoe by Bass is the perfect dressy boot for this fall. They feature genuine leather uppers that mold to your feet, two elastic panels on the side for easy wear, padded footbed for comfort, and a man made sole. Shaft 5" Style: Amsterdam more

    $69.99

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    Johnston & Murphy Men's Larsey Dress Boot,Tan Italian Calfskin,11.5 M US

    Johnston & Murphy Men's Larsey Dress Boot,Tan Italian Calfskin,11.5 M US

    Side-zip entry and a heel pull make stepping into this sleek dress boot easy and comfortable. more

    $119.97

    FREE shipping

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    Men's Rockport Insider Details Chelsea Boot - Black Leather Boots

    Men's Rockport Insider Details Chelsea Boot - Black Leather Boots

    Free Shipping & Free Returns!

    Equal parts functional and sophisticated, our Insider Details Collection of men's dress shoes will support you during any activity. Paired perfectly with a suit or jeans on the weekends, these are a must have closet essential. Built with an EVA footbed... more

    $124.95

    FREE shipping

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    (150,000+)
    Steve Madden M-Boost Men's Dress Zip Boots

    Steve Madden M-Boost Men's Dress Zip Boots

    Free Shipping on all orders! Give your ego a boost in these stylishly attractive boots! ; Synthetic leather upper. Strap and buckle detail highlight the ankle. Side-zip closure. Cushioned footbed. Fabric lining. Man-made sole. Imported. Measurements: ;... more

    $79.99 $40.99

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    Crown by Born Aston Wingtip Shoes - Leather (For Men) ? DARK BROWN VEG

    Crown by Born Aston Wingtip Shoes - Leather (For Men) ? DARK BROWN VEG

    Get 30% off $100 or more with PCZILLAUS5

    CLOSEOUTS . Handsomely updated and a bit less formal than its conservative predecessors, the Aston leather wingtip shoe from Crown by Born is a winning accompaniment to dress denims. Available Colors: DARK BROWN VEG. Sizes: 9, 9.5, 10, 10.5, 11, 11.5, 12. more

    $180.00 $81.16

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    (700,000+)
    Born Men's Hemlock Boot

    Born Men's Hemlock Boot

    Rugged meets tailored in this versatile boot, the Born Hemlock. Set in a full-grain leather upper, this men's Born boot features goring panels for a flexible fit. A pull tab makes pulling on this Born mens ankle boot a cinch. For chic, sleek style, the... more

    $98.95

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    Men's Born 'Julian' Chelsea Boot

    Men's Born 'Julian' Chelsea Boot

    Tough construction defines a rugged Chelsea boot crafted from weathered suede. Color(s): anthracite suede. Brand: Born. Style Name: Born 'Julian' Chelsea Boot. Style Number: 560859_1. Manufacturer part number H01758 Suede upper/leather lining/rubber... more

    $140.00

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    Nordstrom

    (1,000+)
    Ferrini Suede Alligator Belly Print Cowboy Boots - Wide Square Toe

    Ferrini Suede Alligator Belly Print Cowboy Boots - Wide Square Toe

    Ferrini boots for the man who likes to dress to impress!. Suede vamp in an alligator belly print . Fancy butterfly embroidery decorates shaft . Comfortable cushioned insole . Leather outsole . Vendor Style: 40793-29 . Ferrini boots are handcrafted with... more

    $194.99

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    Ariat Quantum Pro Cowboy Boots - Leather, Round Toe (For Men) ? WEATHERED CHESTNUT

    Ariat Quantum Pro Cowboy Boots - Leather, Round Toe (For Men) ? WEATHERED CHESTNUT

    Get 30% off $100 or more with PCZILLAUS5

    CLOSEOUTS . Infused with Ariat's Quantum Technology for 360-degree, heel-to-toe comfort, Ariat's Quantum Pro cowboy boots offer workday-level comfort in a classy, burnished design that's suitable for everything from dress duds to boot-scootin' night... more

    $269.95 $129.46

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    (700,000+)
    Men's Magnanni 'Ciro' Chelsea Boot

    Men's Magnanni 'Ciro' Chelsea Boot

    Richly burnished leather and a square toe define a sleek Chelsea dress boot that's detailed with a buckled strap. Color(s): black. Brand: MAGNANNI. Style Name: Magnanni 'Ciro' Chelsea Boot (Men). Style Number: 719334. Manufacturer part number 14565-1... more

    $425.00

    FREE shipping

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    Nordstrom

    (1,000+)
    Men's Born 'Mac' Chelsea Boot

    Men's Born 'Mac' Chelsea Boot

    Durable full-grain leather forms an updated Chelsea boot designed to fuse comfort and style. Color(s): black, grey. Brand: Born. Style Name: Born 'Mac' Chelsea Boot (Men). Style Number: 697124. Manufacturer part number H11403 Leather upper and... more

    $119.00

    FREE shipping

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    Nordstrom

    (1,000+)
    Fulinken Genuine Leather Pointed Toe Chat Zip Men Formal Shoes Dress Boots Ankle Boots

    Fulinken Genuine Leather Pointed Toe Chat Zip Men Formal Shoes Dress Boots Ankle Boots

    Pointy toe with zip. Soft and comfortable top layer cow leather, sole stitching reinforcement of double insurance and rubber outsole, to create a classic and fashion formal dress business boots. more

    $120.00

    FREE shipping

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    Alpine Swiss Mens Chelsea Boots Suede Lined Pull On Ankle Shoes

    Alpine Swiss Mens Chelsea Boots Suede Lined Pull On Ankle Shoes

    Men's Sion Slip-On Boots By: Alpine Swiss Have these sleek boots be your new go-to shoe for any of your casual or dress looks!   Product Features: Measures: 4.5" Shafts, 1.5" Heel Weight: 1.75 lbs  Breathable Suede Leather Lining Heel Tab for Easy Pull... more

    $34.99

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    Twisted X Mens Western - Silver Buckle Collection 13" Cowboy Boots Bomber/Bomber

    Twisted X Mens Western - Silver Buckle Collection 13" Cowboy Boots Bomber/Bomber

    Designed for the fella that prefers a traditional western look. The technology and components were developed for all-day comfort without giving up stability and durability. This is the perfect boot for casual and dress wear. Includes a... more

    $169.95

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    EXPRESS Mens Tan Suede Lace Up Boot

    EXPRESS Mens Tan Suede Lace Up Boot

    . These Work-inspired, Ankle Covering Lace Ups Will Add A Touch Of Texture To Your Jeans And Dress Pants Alike. Durable Rubber Soles Mean You Can Kick It In These For A Long Time. Plus, They've Got A Rugged Plaid Lining For Warmth And A Bit Of Fun.... more

    $138.00

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    Allen Edmonds Cronmok Wingtip Leather Dress Ankle Boots Mens Brown 8

    Allen Edmonds Cronmok Wingtip Leather Dress Ankle Boots Mens Brown 8

    100% Authentic guaranteed ALLEN EDMONDS Cronmok * First quality guaranteed * Brand new in box *Wingtip premium leather upper *Lace up closure for adjustable fit *Leather footbed *V tread leather rubber outsole * 360 degrees Goodyear welted construction... more

    $234.99

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    Born Stock Mens Brown Ankle Boots Shoes M2775 Medium

    Born Stock Mens Brown Ankle Boots Shoes M2775 Medium

    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 6.5 7 more

    $109.93

    FREE shipping

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    Allen Edmonds Cronmok Wingtip Leather Dress Ankle Boots Mens Brown 9

    Allen Edmonds Cronmok Wingtip Leather Dress Ankle Boots Mens Brown 9

    100% Authentic guaranteed ALLEN EDMONDS Cronmok * First quality guaranteed * Brand new in box *Wingtip premium leather upper *Lace up closure for adjustable fit *Leather footbed *V tread leather rubber outsole * 360 degrees Goodyear welted construction... more

    $234.99

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    Men's Kennebec Casual Chukka Boots 11.5 M(D) Gray

    Men's Kennebec Casual Chukka Boots 11.5 M(D) 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 10.5 W(Ee) Gray

    Men's Kennebec Casual Chukka Boots 10.5 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

    go to store
    (2,500+)
    Men's Kennebec Casual Chukka Boots 10.5 M(D) Gray

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

    go to store
    (2,500+)

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