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| Best Seller  | Dryshod Sod Buster Mens Ankle Boot Moss/Grey 8 SDB-MA-MS-008 Dryshod Sod Buster Mens Ankle Boot Moss/Grey 8 SDB-MA-MS-008. 100percent waterproof top to bottom Hydrokote water repellent so water rolls off and dries in seconds only genuine hand-laid rubber (no PVC PU or TPR) reinforced tuck board with rigid shanks... more | FREE shipping go to store |
 | Xtratuf Leather 6in Ankle Deck Boot - Men's Black 8 XAL-000-BLK-080 Xtratuf Leather 6in Ankle Deck Boot - Men's Black 8 XAL-000-BLK-080. The Boatyard series is a 100percent waterproof collection of leather work boots that provide traction comfort and protection. The leather version of the beloved Ankle Deck Boot is... more | FREE shipping go to store |
| Best Seller  | Xtratuf 6 in Ankle Deck Boots - Men's Navy/Red 8 22733-NVY-080 Xtratuf 6 in Ankle Deck Boots - Men's Navy/Red 8 22733-NVY-080. Xtratuf crafted these Men's Footwear with a slip-resistant Chevron outsole that provides superior traction on even the slipperiest docks. Xtratuf Men's 6in Ankle-Height Deck Boots are... more | FREE shipping go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 2cm 100% Calf Leather, 100% Rubber. Made in Italy. more | $727.64 $593.75 FREE shipping go to store |
 | Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. more | $727.64 $593.75 FREE shipping go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 4cm, Height: 14cm, Sole: 2.5cm 100% Leather, 100% Rubber, 72% Polyester, 28% Elastane. Made in Italy. more | $694.06 $599.66 FREE shipping go to store |
 | Men's Ann Demeulemeester Stef Chelsea Ankle Boots - Black - Casual boots Synonymous with timeless elegance, the Chelsea boot gets a low-key update from Ann Demeulemeester. A menswear classic, they will go with a navy or grey suit, or with jeans and a... more | $833.99 $512.40 FREE shipping go to store |
 | Coach X Tabitha Simmons Velvet Black Chelsea Ankle Booties Velvet Upper Man-Made Leather Lining And Footbed Rubber Outsole Zip Closure Shaft: 4 1/2" Height, 9" Circumference 1" Heel This Special Collaboration Between Coach And Designer Tabitha Simmons... more | go to store |
 | Chaco Fields Chelsea Shoes - Men's Black 8.5 Medium JCH107461-8.5 Chaco Fields Chelsea Shoes - Men's Black 8.5 Medium JCH107461-8.5. Elastic gore on both sides allows you to slip in and adventure on. Specifications for Chaco Fields Chelsea Shoes - Men's: Manufacturer: Chaco Gender: Male Age Group: Adults Men's Shoe... more | FREE shipping go to store |
 | Chaco Fields Chelsea Shoes - Mens Maple Brown Suede 8 JCH108723-8 Chaco Fields Chelsea Shoes - Mens Maple Brown Suede 8 JCH108723-8. Elastic gore on both sides allows you to slip in and adventure on. Specifications for Chaco Fields Chelsea Shoes - Men's: Manufacturer: Chaco Gender: Male Age Group: Adults Men's Shoe... more | FREE shipping go to store |
 | Chaco Fields Chelsea Shoes - Mens Maple Brown Suede 8.5 JCH108723-8.5 Chaco Fields Chelsea Shoes - Mens Maple Brown Suede 8.5 JCH108723-8.5. Elastic gore on both sides allows you to slip in and adventure on. Specifications for Chaco Fields Chelsea Shoes - Men's: Manufacturer: Chaco Gender: Male Age Group: Adults Men's... more | FREE shipping go to store |
 | Reposhing This Item I Purchased From @Mltldl. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more | go to store |
 | Reposhing This Item I Purchased From @Pinetreeposh. Loved It, But They Are Too Small I’m Usually A 9 Or 9.5. These Fit So Snug, I Would Compare Them To An 8, Maybe An 8.5. more | go to store |
 | Free People Shoes | Free People Atlas Black Puffer Chelsea Ankle Boots | Color: Black | Size: 8.5 Please Read Description Above About This Brand New Puffer Boot! more | go to store |
 | Free People James Chelsea Ice Leather Clear Lug Sole Ankle Boots Women's Size Eu 39/ Us 8m. New With Defects. Store Stock Display Pair. No Tags, No Original Box. Faint Light Gray Mark On Ankle Of One Boot. A Few Imperfections On Block Heel Surface... more | go to store |
 | Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8 There Are A Euro Size 41 (Us 8) Free People Cowboy/ Chelsea Boot Style Stretchy On The Side Like A Chelsea Boot Small Heel more | go to store |
 | Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 38 | Color: Brown/Red | Size: 8 Free People Castillo Chelsea Boot - Size 38 Eu/ Us Women’s 8. Fits Size 8.5 Snug. Purchased From Free People Directly Years Ago And Held Onto Them Because They’re So Cute But Unfortunately A Little Too Small For Me. Made With Real Patent Leather And... more | go to store |
 | Madewell Shoes | Madewell Chelsea Snake Embossed Ankle Boots New! | Color: Red | Size: 8.5 Runs Small; Order 1/2 Size Up. Details An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. - 1 3/4" Heel (Size 8.5) - 3" Shaft - Pull-On Style With Elastic Gore Insets -... more | go to store |
 | Free People Shoes | Free People Vegan Chelsea Gray Ankle Boots | Color: Gray | Size: 8 Size 8 Block Heel In Good Condition more | go to store |
 | Free People Shoes | Free People Brown Leather Chelsea Ankle Booties 38 | Color: Brown | Size: 8 Free People Brown Leather Chelsea Ankle Booties - Zip Up Heels - Leather Sole - Heel Height: 1” Size: Euro 38 / 8 (Hj) more | go to store |
 | Kate Spade Shoes | Kate Spade Leah Leopard Print Chelsea Ankle Boots | Color: Brown/Tan | Size: 8.5 - Condition 7.5/10, Minimal Wear, Main Flaw Is Rubbing On Front Of Toe, (Not Too Noticeable, Look At Photos For Flaws) - Kate Spade Leah Calf Hair Leopard Print Ankle Boots, Features Chelsea / Stretch Panels On The Side, A Block Heal, Kate Spade Emblem... more | go to store |
 | Madewell Bryce Chelsea Camel Brown Suede Ankle Booties Boots Size 8.5 Good Preowned Condition Streamlined And Undeniably Cool, This Suede Chelsea Boot Has A A Low-Key Western Vibe We Love. Cuff Up Or Tuck In Your Jeansthese Hit Right At The Ankle. -... more | go to store |
 | Zara Shoes | Brown Suede Chelsea Ankle Boot | Color: Brown/Tan | Size: 8 Tall Ankle Boot Suede Chelsea Boot From Zara, Worn Once! more | go to store |
 | Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more | go to store |
 | Reposhing This Item I Purchased From @Ellenjv. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more | go to store |
 | Sz 39 Eu Sz 8.5 Us Great Condition, Very Light Signs Of Wear 3” Heel Made In Spain more | go to store |
 | Madewell The Ryan Black Chelsea Leather Pull On Ankle Boots In Size 8.5. In Good Preowned Condition With Some Scuffs And Wear As Shown. Bin Hg3 more | go to store |
 | Bran New In A Box. Size 7.5 But They Run 1 Size Bigger =8.5. Genuine Embossed Croc Leather. Black Elastic Sides, Pointy Toe. Curved Hills 1.75” more | go to store |
 | Never Worn Out Of The Home. Smoke And Pet Free Home. Amazing Condition more | go to store |
 | Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede Size 38/Us 8 Nwob New Without Box. Store Display Model. Minor Wear From Being Tried On In A Retail Environment. Please See Photos. Never Worn Outside. Smoke Free Home. Fast... more | go to store |
 | Follow Us, New Items Posted Almost Daily. Plus Bundle 3 Or More And Save Automatically 25% Off (Lowest Offer) Offers, Questions, And Comments Always Welcome. Fast Shipping Always, Please Throughly Check All Photos For Wear, Condition, And Style. more | go to store |
 | Soft Light Tan Leather Booties Buckle Strap And Adjustable Closure 3” Sturdy Heel Little Leather Bows On The Back Heel With The Kate Spade Logo Super Cute And Versatile Good Condition, Some Light Water Marks See All Photos For Condition I Ship Quickly... more | go to store |
 | Reposhing This Item I Purchased From @Sydney_coop21. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more | go to store |
 | J. Crew Shoes | J Crew Sherpa Lined Chelsea Ankle Boot | Color: Black | Size: 8 Awesome Pair Of Barely Worn Ankle Chelsea Style Leather Boots In Excellent Pre-Owned Condition. more | go to store |
 | Madewell Size 8 The Ivy Croc Embossed Leather Chelsea Boots Ankle Boots In Brown Platform Utilitarian Lug Soles In Excellent Almost Like New Condition. Very Clean Inside & Out. Tags: Classic Chunky Lug Soles Neutral Versatile Business Casual Office... more | go to store |
 | Madewell Shoes | Madewell Chelsea Ankle Bootie | Color: Black | Size: 8 Leather, Slip-On Chelsea Ankle Bootie In Black. 2 1/4” Block Heel. Size 8. Worn But Still In Good Condition With Plenty Of Life Left. more | go to store |
 | Kenetrek Everstep Orthopedic Boots - Men's Brown 8.5 US Medium ES-420-OPNI 8.5 Med Kenetrek Everstep Orthopedic Boots - Men's Brown 8.5 US Medium ES-420-OPNI 8.5 Med. Some of Kenetrek's customers have had surgeries a series of foot and ankle issues or just spent most of their lives pursuing activities that led to overuse... and they... more | FREE shipping go to store |
 | Zamberlan Vioz Lux GTX RR Backpacking Shoes - Men's Wide Waxed Brick 8 1996WBM-W-42-8 Zamberlan Vioz Lux GTX RR Backpacking Shoes - Men's Wide Waxed Brick 8 1996WBM-W-42-8. Made from full-grain waxed leather these Men's Hiking Boots & Shoes are waterproof and provide excellent ankle support to help you stay steady even on inclines and... more | FREE shipping go to store |
 | Zamberlan Vioz Lux GTX RR Backpacking Shoes - Men's Waxed Brick 8.5 US Medium 1996WBM-42.5-8.5 Zamberlan Vioz Lux GTX RR Backpacking Shoes - Men's Waxed Brick 8.5 US Medium 1996WBM-42.5-8.5. Made from full-grain waxed leather these Men's Hiking Boots & Shoes are waterproof and provide excellent ankle support to help you stay steady even on... more | FREE shipping go to store |
 | Zamberlan Vioz Lux GTX RR Backpacking Shoes - Men's Waxed Brick 8 US Medium 1996WBM-42-8 Zamberlan Vioz Lux GTX RR Backpacking Shoes - Men's Waxed Brick 8 US Medium 1996WBM-42-8. Made from full-grain waxed leather these Men's Hiking Boots & Shoes are waterproof and provide excellent ankle support to help you stay steady even on inclines... more | FREE shipping go to store |
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