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Best Mens Chukka Boots - Buying Guide

Last Updated: 04/24/2019

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  #1

BRUNO MARC NEW YORK Men's Urban-06 Suede Leather Chukka Ankle Boots

Asin: B072K95V7D

Pull off an edgy and comfortable look with these casual chelsea boots! Featuring Suede Leather upper, Slip on design, classic round toe design, elastic side panel for easy on and off. Finished with smooth fabric Lining, cushioned footbed for comfort, and non-skid outsole.

Features

  • Durable manmade sole
  • Heel measures approximately 1
  • Platform measures approximately 0.5
  • Slip On Plain-toe chukka boot featuring suede upper
  • Flexible and Comfort Chukka Boots
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Brand: BRUNO MARC NEW YORK

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  #2

Steve Madden Men's Harken Chukka Boot

Model: Harken   |    Mpn: HARKEN-203   |    PartNumber: HARKEN-203   |   Asin: B00C85OPOM

Widely spaced stitches around the outsole pop in this classic chukka from Steve Madden.

Features

  • Chukka boot featuring blind-eyelet lacing and slightly distressed finish. Textile lining
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Brand: Steve Madden   |   Manufacturer: Steve Madden Footwear Mens

Item Dimensions: 0.7 x 5 x 5 inches (1.8 x 12.7 x 12.7 cm)   |   Package Dimensions: 4 x 8 x 12 inches (10.2 x 20.3 x 30.5 cm)

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  #3

Clarks Men's Stinson Hi Chukka Boot

Model: Stinson Hi   |    Mpn: 26063446   |    PartNumber: 26063446   |   Asin: B00BM0RRWG

Classic wallabee style

Features

  • Classic leather chukka boot with two-eye lacing and blind eyelets featuring rolled moccasin toe and contrast crepe outsole
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Brand: CLARKS   |   Manufacturer: Clarks

Item Dimensions: 0.7 x 5 x 5 inches (1.8 x 12.7 x 12.7 cm)   |   Package Dimensions: 4 x 8 x 12 inches (10.2 x 20.3 x 30.5 cm)

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  #4

Skechers Men's Segment Melego Leather Chukka Waterproof Boot

Model: Segment Melego   |    Mpn: 64522-CDB   |    PartNumber: 64522-CDB   |   Asin: B00SLIQ2W8

Expand your taste in style and comfort with the Relaxed Fit Segment - Melego by SKECHERS . Smooth oiled leather upper is waterproof. Lace-up closure. Soft fabric lining. Relaxed Fit design for a roomy comfortable fit. Gel Infused Memory Foam cushioned comfort insole. Shock absorbing supportive midsole. Flexible rubber high traction outsole. Imported. Measurements: Weight: 1 lb 1 oz Product measurements were taken using size 12, width D - Medium. Please note that measurements may vary by size. Weight of footwear is based on a single item, not a pair.

Features

Brand: Skechers   |   Manufacturer: Skechers

Item Dimensions: 0.7 x 5 x 5 inches (1.8 x 12.7 x 12.7 cm)   |   Package Dimensions: 0.7 x 11 x 14 inches (1.8 x 27.9 x 35.6 cm)

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  #5

Palladium Men's Pampa Hi Canvas Boot

Model: Pampa Hi-PARENT   |    Mpn: 02352-090   |    PartNumber: 02352-090   |   Asin: B003ZYDLKY

Blending combat boot and high-top sneaker, Palladium gives you a distinctive casual look.

Palladium's original Pampa boot is so rugged it was used by the French Legion is deserts of North Africa. Bring the same durable dependability to your wardrobe with the Pampa Hi. This understated offering in canvas proves indispensable for urban maneuvers with a reinforced toe, high-walled rubber sole, and deep treads for good grip wherever you march. Complementing laces offer a sophisticated monochrome vibe that has you perfectly at ease in Palladium.

Features

  • High top sneaker-inspired boot in canvas featuring wrap-around textured rubber outsole and logo patch on tongue
  • Lace-up
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Brand: Palladium   |   Manufacturer: Palladium

Package Dimensions: 4.65 x 9.06 x 13.15 inches (11.8 x 23.0 x 33.4 cm)

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  #6

Skechers Men's Relaxed Fit Segment - Dorton Boot

Model: 64263   |    Mpn: 64263-1   |    PartNumber: 64263-1   |   Asin: B00JA7TS34

Leather Imported: Made in China Synthetic sole Shaft measures approximately 5" from arch Platform measures approximately 0.75 inches Boot opening measures approximately 10.5" around Chelsea ankle boot featuring oiled-leather upper with concealed-goring side panels and rear pull loop Gel-infused memory foam insole Shipping Note: Shipping to Alaska, Hawaii, PO Boxes and APO addresses not available for this item

Features

  • Chelsea ankle boot featuring oiled-leather upper with concealed-goring side panels and rear pull loop
  • Gel-infused memory foam insole
  • Reinforced stitched seams
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Brand: Skechers   |   Manufacturer: Skechers

Package Dimensions: 4 x 8 x 12 inches (10.2 x 20.3 x 30.5 cm)

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  #7

Steve Madden Men's Hestonn

Model: HESTONN   |    Mpn: SMH3621806   |    PartNumber: SMH3621806   |   Asin: B07G2HKKLM

Rich, smooth leather dresses up or down in this chukka offering from Steve Madden.

Features

Brand: Steve Madden   |   Manufacturer: Steve Madden

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  #8

Kunsto Men's Leather Classic Brogue Boots

Model: 40#4649   |   Asin: B017EOO62W

About Kunsto: Kunsto's mission has been to supply the customer with top-quality comfortable, durable, contemporary casual footwear that is styled and priced right. Everything they do is driven by these five attributes: quality, comfort, durability, style. That is what makes Kunsto shoes one of the best footwear values in the market.

Features

  • Guarantee 100% Top Grain Genuine Leather Upper.
  • The ankle boots are very comfortable, fashionable, and functional.
  • Padded collar wingtip boot featuring lace-up vamp, brogue-perforated trim, recycled mesh lining, Organic cotton canvas laces, 55 inches lace length
  • Bicycle Printed on the rubber out-sole bottom
  • Distressed/Faded retro genuine Leather Upper with the mesh lining allow me keeps foot dry and clean, it's perfect for wearing to work, casual occasions...
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Brand: Kunsto

Item Dimensions: 5 x 4 x 11 inches (12.7 x 10.2 x 27.9 cm)   |   Package Dimensions: 4 x 5 x 12 inches (10.2 x 12.7 x 30.5 cm)

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  #9

London Fog Mens Belmont Chukka Boot

Model: LFM-BELMONT   |   Asin: B07DP4ZXLL

Explore the world in these London Fog Chukka Boots! London Fog is one of the oldest and most established U.S. fashion brands. For over 90 years, the brand has embodied a classic metropolitan appeal. Today, London Fog is ranked as the #1 recognized brand of outerwear in the United States. London Fog continues to enjoy iconic status.

Features

Brand: London Fog

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  #10

Timberland Men's Groveton LTT Chukka Leather & Fabric Sneaker

Model: -   |    Mpn: TB06743A001   |    PartNumber: TB06743A001   |   Asin: B01IB826UY

Uppers made with 100% premium leather from an LWG Silver-rated tannery and 100% recycled CORDURA Ecomade canvas. 50% recycled PET Lining. 15% recycled rubber outsole. Gripstick rubber. Patented L7 lug design features multi-directional leading edges with beveled lug sidewalls. Imported.

Features

  • Make sure your men's street shoes can handle your adventures! Our Groveton mixed-media chukkas feature recycled materials, cushiony footbeds, and streamlined styling that's great dressed up or down.
  • ON THE TRAIL OR THE STREET, Timberland has the styles you'll love to wear. From ankle boots & sneaker boots to sandals & boat shoes, Timberland will keep you on your feet & looking fabulous.
  • TIMBERLAND HAS YOU COVERED whether you're looking for men's boots, women's boots, or kids boots. For the best in hiking boots, rain boots, work boots, casual shoes & boots & more, choose Timberland.
  • WHAT YOU NEED IN THE OUTDOORS: Timberland has the gear you need for all your outdoor adventures, including jackets and coats for outdoor activities, backpacks and luggage & outdoor accessories.
  • THE BEST IN OUTDOORS: Trust Timberland's line of high-quality men's, women's, and kids boots. hiking boots, outdoor gear, and activewear for all your activities from the trail to the sea to the streets.
  • See more on Amazon...

Brand: Timberland   |   Manufacturer: Timberland

Item Dimensions: 0.7 x 5 x 5 inches (1.8 x 12.7 x 12.7 cm)   |   Package Dimensions: 0.7 x 11 x 14 inches (1.8 x 27.9 x 35.6 cm)

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  #11

Red Wing Men's Iron Ranger 6" Boot

Model: 6" Iron Ranger   |    Mpn: 8113   |    PartNumber: 8113   |   Asin: B0032UYNKI

Handcrafted in the USA with durable stitch-down welt construction and premium quality leather, the Iron Ranger boot from Red Wing will offer years of comfortable wear. This robust boot is built on a non-marking, oil-resistant sole and handsomely detailed with contrast stitching, a cap toe, and high polish hooks and eyelets.Dear first time buyers, Red Wing Shoes tend to run larger than your regular shoe size. Please take this into consideration when purchasing a pair.Please note, in the manufacturing process, staples are used to adhere the insole to the plastic last. These staples may penetrate the surface of the insole leaving small holes and pushing up a small amount of the grain of the leather insole. Care instruction-Use warm water and a soft bristle brush to remove stuck-on dirt. Then use a clean, dry cloth to wipe away any remaining excess dirt

Handcrafted in the USA with durable stitch-down welt construction and premium quality leather, the Iron Ranger boot from Red Wing will offer years of comfortable wear. This robust boot is built on a non-marking, oil-resistant sole and handsomely detailed with contrast stitching, a cap toe, and high polish hooks and eyelets.

Features

  • The product is natural leather and its easy for scuffs to happen but they rub out.This can be removed by a soft dry cloth and lightly buffed out the scuffs. The shoe has a steel shank
  • Many customers buy Red Wing Heritage footwear 1/2 size smaller than their normal size. Goodyear welt construction, triple stitched quality
  • Features a bump toe for more room up-front. Double layer leather toe cap and leather heel pocket
  • Outsole: Nitrile Cork , Insole:Leather, Shank: Steel ; Laces: 48-inch Black/Brown Taslan Lace. Fits a variety of foot shapes
  • Care instructions -Use warm water and a soft bristle brush to remove stuck-on dirt and then use a clean, dry cloth to wipe away any remaining excess dirt
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Brand: Red Wing   |   Manufacturer: Red Wing Heritage

Package Dimensions: 4 x 8 x 12 inches (10.2 x 20.3 x 30.5 cm)

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  #12

Timberland Women's Nellie Double Waterproof Ankle Boot

Model: Nellie Double WP   |    Mpn: TL_TB023308   |    PartNumber: TL_TB023308   |   Asin: B00BCJXLIG

Rugged with the perfect touch of femininity, the Nellie Chukka from Timberland will take you on your next adventure. Waterproof full-grain leather uppers with a round toe. Easy lace-up closure with laces made from 100% PET (recycled plastic bottles). Rustproof hardware. Cushioned and removable footbeds for added comfort. Anti-fatigue midsole uses geometric cone support to provide standing comfort, shock-absorption and energy return. Rubber lug outsole offers durability and maximum traction. Breathable mesh linings and footbed covers are made from recycled plastic bottles. Imported. Measurements: Heel Height: 1 in Weight: 1 lb 4 oz Shaft: 4 in Platform Height: 1 2 in Product measurements were taken using size 7.5, width B - Medium. Please note that measurements may vary by size. Weight of footwear is based on a single item, not a pair.

Features

  • CLASSIC STYLE: Our comfy, customer-favorite Nellie boots are the perfect blend of rugged and feminine. Styled with everything from skirts to ripped jeans, wear these waterproof boots year-round. Featuring premium full-grain waterproof leather uppers.
  • NOT JUST FOR THE TRAIL: Whether you're trekking the mountains or hiking downtown streets, Timberland has the styles you'll love to wear. From ankle boots & sneaker boots to sandals & boat shoes, Timberland will keep you on your feet & looking fabulous.
  • TIMBERLAND BOOTS are synonymous with quality workmanship. Whether you're looking for mens boots, womens boots, or kids boots, Timberland has you covered. For the best in hiking boots, rain boots, work boots, casual shoes & boots & more, choose Timberland.
  • WHAT YOU NEED IN THE OUTDOORS: Timberland isn't just for high-quality mens, womens, and kids boots. We have the gear you need for all your outdoor adventures, including jackets and coats for outdoor activities, backpacks and luggage & outdoor accessories.
  • THE BEST IN OUTDOORS: See how Timberland's line of outdoor wear stacks up to hiking boots, casual shoes, and street boots from brands like Keen, Lucky, Toms, Dansko, Doc Martens, Uggs, Skechers, Vionic, Maelstrom, Justin, Hunter, Bogs, Nike, or Sorel.
  • See more on Amazon...

Brand: Timberland   |   Manufacturer: Timberland

Item Dimensions: 0.7 x 5 x 5 inches (1.8 x 12.7 x 12.7 cm)   |   Package Dimensions: 4 x 8 x 12 inches (10.2 x 20.3 x 30.5 cm)

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  #13

UGG Men's Neumel Chukka Boot

Model: Neumel   |    Mpn: 3236   |    PartNumber: 3236   |   Asin: B01MSWOVEY

UGG DNA meets California leisure in the Neumel, which has become an icon of street style for its soft wool lining and chukka silhouette. Crafted from soft suede, this best-selling boot is cushioned, durable, and pairs with anything. Wear indoors as a slipper or out with your favorite denim. Cushioning foam insole with UGGpure wool lining to naturally wick away moisture

Features

  • DETAILS: Suede / UGGpure wool lining / Cushioning foam insole with UGGpure wool lining to naturally wick away moisture / Lightweight and flexible EVA / 4.25" shaft height.
  • COMFORT: Women, men, young, old, teens or tweens can rock these! Add comfort to your day look, work, beach, traveling, shopping, boating, walking or just to relax in. Pair it with any type of outfit from casual to sporty and everywhere in between. Great gift idea!
  • COASTAL CLASSIC: By the 80's, the UGG brand had become a symbol of relaxed southern California culture. UGG stepped into the world of high fashion in 2011 with UGG Collection, fusing the timeless craft of Italian shoemaking with the luxe feel of sheepskin.
  • ANIMAL WELFARE: UGG only purchases sheepskin from suppliers that comply with our strict animal welfare policy. They DO NOT get sheepskin from; the Middle East or North Africa or from countries that do not have standards that regulate the treatment of animals.
  • AUTHENTIC: Counterfeiters try to benefit from the popularity by fooling customers into purchasing fake products. We can assure you this is an authentic product. Renowned for the luxurious comfort of twin-faced sheepskin and exceptional craftsmanship.
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Brand: UGG   |   Manufacturer: UGG

Item Dimensions: 5.5 x 9.5 x 14 inches (14.0 x 24.1 x 35.6 cm)   |   Package Dimensions: 5.5 x 9.5 x 14 inches (14.0 x 24.1 x 35.6 cm)

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  #14

BRUNO MARC NEW YORK Men's Classic Original Suede Leather Desert Storm Chukka Boots

Asin: B01A7D0YEG

Give your outfit a classy look with these chukka Featuring suede upper, three eyelets lace up with elastic panel design for easy on/off wear, and contrast stitch detailing on vamp for added style, and classic plain toe Design, Finished with smooth suede and textile Lining, cushioned footbed for comfort, and non-skid outsole.

Features

  • manmade sole
  • Heel measures approximately 1
  • Platform measures approximately 0.5
  • Plain-toe chukka boot featuring suede upper and lace-up front closure
  • Midsole stripe
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Brand: BRUNO MARC NEW YORK

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  #15

Clarks Originals Men's Desert Boot

Model: 3169   |    Mpn: CLK_03683   |    PartNumber: CLK_03683   |   Asin: B0007MCUTK

Clarks remakes its signature desert boots in supple suede. 4 tonal eyelets at the lace-up vamp. Contrast welt stitches at the gum sole. Cushion leather insole.

For a classic that s graced men s fashion for over 50 years, check out this Desert boot from Clarks. This chukka features a leather upper with a two-eyelet lace-up for a casual fit. Beneath, a plantation crepe sole delivers legendary cushioning for all-day comfort.

Features

  • Stabilizing suede-lined heel counter
  • Platform measures approximately 0.5 inch
  • Heel measures approximately 1 inch
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Brand: CLARKS   |   Manufacturer: Clarks

Item Dimensions: 5 x 8 x 20 inches (12.7 x 20.3 x 50.8 cm)   |   Package Dimensions: 4 x 8 x 12 inches (10.2 x 20.3 x 30.5 cm)

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  #16

Rockport Men's Rugged Bucks Waterproof Boot

Model: Rugged Bucks WP Boot   |    Mpn: V74355-001   |    PartNumber: V74355-001   |   Asin: B00AZX45N0

Rugged readiness comes in a remarkably handsome package.

Features

  • Rugged, mid-cut boot with padded collar and added bounce-back features
  • Comfort system designed to provide lightweight shock absorption.
  • Hydro-Shield waterproofing construction
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Brand: Rockport   |   Manufacturer: Rockport Footwear Mens

Item Dimensions: 0.7 x 5 x 5 inches (1.8 x 12.7 x 12.7 cm)   |   Package Dimensions: 4 x 8 x 12 inches (10.2 x 20.3 x 30.5 cm)

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  #17

Men's Eddie Bauer K-6 Boot

Model: 91900025   |    Mpn: 91900025   |    PartNumber: 91900025   |   Asin: B077GDS63W

We're proud to reintroduce the K-6 hiking boot that first appeared in the Eddie Bauer catalog in 1964. Finely crafted of waterproof full-grain leather using Goodyear welt construction, this is a boot that will last a lifetime. WeatherEdge waterproof/breathable membrane provides maximum protection from the wet.

Features

  • InsoFit Pro ergonomic polyurethane footbed with stabilizing heel cup and superior forefoot support
  • Sure-footed Vibram outsole
  • Comes with two lace colors
  • Men's sizes 8-12, 13, 14
  • Cushioning EVA midsole
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Brand: Eddie Bauer   |   Manufacturer: Eddie Bauer

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  #18

Steve Madden Men's Dazier Chukka Boot

Model: DAZI01M1   |   Asin: B07HRNQ95Z

Sporty meets classic on the dazier, a high top lace up featuring a white sporty sole on a classic upper.

Features

Brand: Steve Madden   |   Manufacturer: Steve Madden

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  #19

Jeffrey Tyler Mens Greenwich Chukka Boot Shoes

 PartNumber: JTYLERGreenwich   |   Asin: B07PM847VL

Uptown sleek meets downtown cool in the Greenwich men's chukka boot from Jeffrey Tyler. Cut with an always-classic chukka silhouette, it's the perfect match for your easygoing attitude. Brand: Jeffrey Tyler. Department: Men. Style Name: Greenwich. Materials: PU Upper, TPR Outsole. Lace Up Front Closure With A Classic Chukka Silhouette. Traction Sole For Secure Footing. Shaft Height Measures Approximately 4" From Heel. Boot Opening Measures Approximately 11" Around. Heel Height Measures Approximately 1". NOTE: All Measurements Taken On Size US 11. Measurements Will Vary By Size. Made In China.

Features

  • PU Upper, TPR Outsole
  • Lace Up Front Closure With A Classic Chukka Silhouette
  • Traction Sole For Secure Footing
  • Shaft Height Measures Approximately 4 From Heel
  • Heel Height Measures Approximately 1
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Brand: Jeffrey Tyler   |   Manufacturer: Jeffrey Tyler

Item Dimensions: 5 x 9 x 14 inches (12.7 x 22.9 x 35.6 cm)   |   Package Dimensions: 5 x 9 x 14 inches (12.7 x 22.9 x 35.6 cm)

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  #20

Steve Madden Men's Noland Chukka Boot

Model: NOLA01M1   |   Asin: B07J2627PF

Although laid-back in silhouette, the no land chukka looks polished with a quality leather upper and will blend seamlessly into business-casual and weekend getups alike.

Features

Brand: Steve Madden   |   Manufacturer: Steve Madden

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  #21

UGG Men's Beach Moc Chukka Boot

Model: 1101502   |   Asin: B07DP1RFSB

The perfect boat shoe and chukka hybrid. Featuring an energy comfort insole system and drainage ports for quick dry and breathability. Fully machine washable, making this the perfect every day shoe.

Features

  • enerG comfort insole system
  • Treadlite by UGG outsole
  • Machine washable
  • Soft-full grain nubuck upper with moccasin detail
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Brand: UGG   |   Manufacturer: UGG

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  #22

Timberland Men's Premium Wp Chukka Newman

Asin: B07B6CK1QS

Amazon carries Timberland footwear for men, women, and kids: sandals, boots, casual oxfords, tall boots, hiking boots, waterproof boots, winter boots, and women's shoes and boots. Timberland makes rugged, durable, comfortable waterproof leather boots. Timberlands are premium and popular, bringing style, comfort, performance and eco-conscious elements to their leather waterproof shoes and boots. Timberland wheat six inch boot is waterproof, insulated, and a best seller.

Features

  • Upper made with premium leather from an LWG Silver-rated tannery
  • Seam-sealed construction
  • Padded Collar
  • Nylon shank for arch support
  • Rubber lug outsole
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Brand: Timberland   |   Manufacturer: Timberland

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  #23

Blundstone Mens Active Series Boots, Brown

Model: 1388   |    Mpn: 1388   |    PartNumber: 1388   |   Asin: B07PXG7Y8V

Made for warm-weather adventures, Blundstone Summer boots combine breathability with an ultra lightweight design. Built for comfort, they flex and support your feet with every step you take

Features

  • Water repellent suede
  • Ultra lightweight and breathable
  • Feather flex technology supports and flexes
  • Comfort footbed for ultimate shock absorption
  • Anti-microbial lining
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Brand: Blundstone   |   Manufacturer: Blundstone

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Looking For Something Else? Search

Most Popular
New Releases

  1. Men's Eddie Bauer K-6 Boot
  2. Steve Madden Men's Dazier Chukka Boot
  3. Jeffrey Tyler Mens Greenwich Chukka Boot Shoes
  4. Steve Madden Men's Noland Chukka Boot
  5. UGG Men's Beach Moc Chukka Boot
  6. Timberland Men's Premium Wp Chukka Newman
  7. Blundstone Mens Active Series Boots, Brown

Most Wished For

  1. Kunsto Men's Leather Classic Brogue Boots
  2. BRUNO MARC NEW YORK Men's Urban-06 Suede Leather Chukka Ankle Boots
  3. London Fog Mens Belmont Chukka Boot
  4. Clarks Men's Stinson Hi Chukka Boot
  5. Timberland Men's Groveton LTT Chukka Leather & Fabric Sneaker
  6. Red Wing Men's Iron Ranger 6" Boot
  7. Timberland Women's Nellie Double Waterproof Ankle Boot
  8. Steve Madden Men's Harken Chukka Boot

Most Gifted

  1. BRUNO MARC NEW YORK Men's Urban-06 Suede Leather Chukka Ankle Boots
  2. UGG Men's Neumel Chukka Boot
  3. Clarks Men's Stinson Hi Chukka Boot
  4. BRUNO MARC NEW YORK Men's Classic Original Suede Leather Desert Storm Chukka Boots
  5. Timberland Women's Nellie Double Waterproof Ankle Boot
  6. Clarks Originals Men's Desert Boot
  7. Rockport Men's Rugged Bucks Waterproof Boot

Top Selling

  1. BRUNO MARC NEW YORK Men's Urban-06 Suede Leather Chukka Ankle Boots
  2. Steve Madden Men's Harken Chukka Boot
  3. Clarks Men's Stinson Hi Chukka Boot
  4. Skechers Men's Segment Melego Leather Chukka Waterproof Boot
  5. Palladium Men's Pampa Hi Canvas Boot
  6. Skechers Men's Relaxed Fit Segment - Dorton Boot
  7. Steve Madden Men's Hestonn



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