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    Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

    Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

    Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more

    $69.99

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    Chelsea Ankle Boots

    Chelsea Ankle Boots

    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

    $694.65 $566.83

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    Best Seller
    Chelsea Ankle Boots

    Chelsea Ankle Boots

    Men's Tod's Chelsea Ankle Boots - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more

    $587.78 $479.63

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    Chelsea Ankle Boots

    Chelsea Ankle Boots

    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

    $662.59 $572.48

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    J. Crew Shoes | J. Crew Gray Leather Ankle Chelsea Boot W/ Ankle Strap And Gold Hardware- Size 8 | Color: Gray | Size: 8

    J. Crew Shoes | J. Crew Gray Leather Ankle Chelsea Boot W/ Ankle Strap And Gold Hardware- Size 8 | Color: Gray | Size: 8

    J. Crew Gray Leather Chelsea Ankle Boot. Made In Italy With 2 Inch Heel, Ankle Strap And Gold Hardware. 03868 Color: Gray Size: Women's 8 more

    $36.00

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    WIDE FIT Darcy Chelsea Boot - black

    WIDE FIT Darcy Chelsea Boot - black

    Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more

    $99.99 $69.99

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    J. Crew Shoes | J. Crew Leather Chelsea Boots Pull On Ankle Boot | Color: Black | Size: 10

    J. Crew Shoes | J. Crew Leather Chelsea Boots Pull On Ankle Boot | Color: Black | Size: 10

    J. Crew Leather Chelsea Boots Pull On Ankle Boot Black Smooth Buttery Leather Size 10 In Great Condition! Finish Your Fall Look In The Smooth Leather J.Crew Chelsea Lexi Boot Featuring A Breathable Leather Lining And Lightly Cushioned, Stationed Insole... more

    $125.00

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    Madewell Shoes | Madewell The Carina Boot In Snake Embossed Leather Ankle Chelsea Boot Booties | Color: Black/Yellow | Size: 6

    Madewell Shoes | Madewell The Carina Boot In Snake Embossed Leather Ankle Chelsea Boot Booties | Color: Black/Yellow | Size: 6

    Excellent Condition Madewell The Carina Boot In Snake Embossed Leather Ankle Chelsea Boot Booties Brand: Madewell Size: Women’s Size 6 Style: 2030756 Carina Color: Burnt Clay Multi 1.5” Stacked Block Heel 5.5” Tall Leather Upper Snakeskin Print Yellow... more

    $68.00

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    Purl Sock Bootie - Blue - Eileen Fisher Boots

    Purl Sock Bootie - Blue - Eileen Fisher Boots

    Women's Eileen Fisher Purl Sock Bootie - Blue - Ankle boots A stretch knit upper provides texture and a custom fit for a streamlined bootie set on a low block heel. more

    $225.00

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    Jemma Lace-up Platform Stretch Knit Bootie - Black - Eileen Fisher Boots

    Jemma Lace-up Platform Stretch Knit Bootie - Black - Eileen Fisher Boots

    Women's Eileen Fisher Jemma Lace-up Platform Stretch Knit Bootie - Black - Ankle boots A lace-up vamp and rear pull-tab lend easy wear to a knit bootie lifted by a subtle platform and chunky block heel. more

    $235.00 $141.00

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    Rhlan Bootie - Black - Eileen Fisher Boots

    Rhlan Bootie - Black - Eileen Fisher Boots

    Women's Eileen Fisher Rhlan Bootie - Black - Ankle boots An elastic gore inset offers a flexible fit in this bootie crafted of supple nubuck leather in a wrap-front design and set on a low block heel. more

    $255.00 $153.00

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    Henry Ankle Chelsea Boot

    Henry Ankle Chelsea Boot

    Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. more

    $732.05 $597.36

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    Henry Country Ankle Chelsea Boot

    Henry Country Ankle Chelsea Boot

    Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. more

    $732.05 $597.36

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    Burgundy Ankle Strap Chelsea Boots

    Burgundy Ankle Strap Chelsea Boots

    Women's Toga Burgundy Ankle Strap Chelsea Boots - Black - Ankle boots Ankle-high buffed calfskin Chelsea boots in burgundy. Signature hardware throughout. more

    $605.00 $315.00

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    Larue Chelsea Ankle Boots

    Larue Chelsea Ankle Boots

    Men's Moncler Larue Chelsea Ankle Boots - Blue - Casual boots Larue Chelsea ankle boots in leather. Round toe Elasticated side panels Rear pull tab Rear logo ring Embossed logo at midsole Debossed logo at heel cap. 100% Leather. more

    $795.00

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    Madewell Shoes | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged | Color: Tan | Size: 8.5

    Madewell Shoes | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged | Color: Tan | Size: 8.5

    Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged Made Of Water-Resistant Suede With A Rugged Lug Sole, These Pull-On Chelsea Boots Are Fully Lined In Real Shearling To Up The Cozy Factor. Basically: All-Weather Boots You'll... more

    $97.00

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    Madewell Shoes | Madewell Ivy Croc Leather Chelsea Boots Lug Sole Platform Ankle Boots Like New | Color: Brown | Size: 8

    Madewell Shoes | Madewell Ivy Croc Leather Chelsea Boots Lug Sole Platform Ankle Boots Like New | Color: Brown | Size: 8

    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

    $75.00

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    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Brown/Tan | Size: 7

    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Brown/Tan | Size: 7

    Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more

    $128.00

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    Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot J8292, Western Cut Ankle Boot. | Color: Brown/Tan | Size: 8

    Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot J8292, Western Cut Ankle Boot. | Color: Brown/Tan | Size: 8

    Reposhing This Item I Purchased From @Deenajwhennen. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more

    $54.00

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    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Tan | Size: Various

    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Tan | Size: Various

    Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more

    $128.00

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    Free People Shoes | Free People Essential Chelsea Boots In Natural Cream Ankle Boots Size 38 Euc | Color: Cream | Size: 8

    Free People Shoes | Free People Essential Chelsea Boots In Natural Cream Ankle Boots Size 38 Euc | Color: Cream | Size: 8

    Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more

    $90.00

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    Madewell Shoes | Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots | Color: Black | Size: 9

    Madewell Shoes | Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots | Color: Black | Size: 9

    Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots Wear To Toes- Scuffing. Rubbing. Minor Scratching At Heels. Gently Used. Good Condition. Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut... more

    $50.00

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    Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | Color: White | Size: 9

    Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | Color: White | Size: 9

    Brand: Free People Style: James Chelsea Boots Heeled Ankle Booties Color: White Material: Leather With Rubber Gum Sole Size: Eu 40, Fits Like A 9 Has A Slightly Narrow Fit In My Opinion, Though I Do Better With Wider Fit Shoes Condition: New, No Box.... more

    $54.00

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    Free People Shoes | Free People Mark Fisher Alexis Ankle Boots Turquoise 9.5 $$228.00 Pre-Owned | Color: Green | Size: 9.5

    Free People Shoes | Free People Mark Fisher Alexis Ankle Boots Turquoise 9.5 $$228.00 Pre-Owned | Color: Green | Size: 9.5

    Free People Mark Fisher Alexis Ankle Boots Turquoise 9.5 Retail $228.00 Pre-Owned Details Style No. 79162384; Color Code: 070 Stand Out With These Statement-Making Ankle Boots, Featuring Wild Textured Uppers And An Architectural Block Heel To Catch All... more

    $140.00

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    Collin Peep Toe Bootie - Black - Eileen Fisher Boots

    Collin Peep Toe Bootie - Black - Eileen Fisher Boots

    Women's Eileen Fisher Collin Peep Toe Bootie - Black - Ankle boots A stretchy knit upper and padded footbed bring flexibility and comfort to every step you take in a peep-toe bootie elevated by a sturdy stacked block heel. more

    $215.00

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    Alpine Genuine Shearling Wedge Bootie - Black - Eileen Fisher Boots

    Alpine Genuine Shearling Wedge Bootie - Black - Eileen Fisher Boots

    Women's Eileen Fisher Alpine Genuine Shearling Wedge Bootie - Black - Wedge boots On-trend style and plush, warm comfort are all the reasons you need to make this shearling-lined wedge bootie your automatic go-to for the season. more

    $275.00 $165.00

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    Quill Platform Wedge Bootie - Black - Eileen Fisher Boots

    Quill Platform Wedge Bootie - Black - Eileen Fisher Boots

    Women's Eileen Fisher Quill Platform Wedge Bootie - Black - Wedge boots Contrast trim along the sole highlights the wedge heel of a modern knit bootie lifted by a wedge heel. more

    $255.00 $100.00

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    J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5

    J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5

    These Are Black Chelsea Ankle Boots That I Wore So Religiously That I Bought Two Pairs When They Were On Sale As Back Up. I Don’t Need Two Extra Pairs Tho So I’m Selling These Now. Have Hardly Been Worn But Were In Storage For A While And They Deserve... more

    $60.00

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    Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 38 | Color: Brown/Red | Size: 8

    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

    $40.00

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    Kate Spade Shoes | Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots | Color: Black/Gray | Size: 7

    Kate Spade Shoes | Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots | Color: Black/Gray | Size: 7

    Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots Beautiful Graphite Dark Truffle Gray Slip On Style With Side Gore Panels Feminine Scallop Details Sweet Back Heel Bow Round Toe Cushioned Insole Leather Sole 3” Block Heel Made In... more

    $70.00

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    Free People Shoes | Heiress X Free People Caleb Chelsea Gold Metallic Ankle Boot - Size 7 | Color: Black/Gold | Size: 7

    Free People Shoes | Heiress X Free People Caleb Chelsea Gold Metallic Ankle Boot - Size 7 | Color: Black/Gold | Size: 7

    In Good Condition, See Last Pictures For Some Slight Scratches (Not Visible While Wearing!) Textured Rubber Heel. Pull Tab In Back For An Easy On/Off. Padded Footbed. more

    $50.00

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    Free People Shoes | Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) | Color: Brown | Size: 6.5

    Free People Shoes | Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) | Color: Brown | Size: 6.5

    Rare Find! Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) Made In Portugal With Real Patent Leather And Meant To Look Distressed. Wooden Sole And Chunky Metal Accents. Slight Creases Near Toes But Not Not Effect The Functionality Of The... more

    $89.00

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    J. Crew Shoes | J. Crew Chelsea Leather Ankle Boot, Size 9 | Color: Black | Size: 9

    J. Crew Shoes | J. Crew Chelsea Leather Ankle Boot, Size 9 | Color: Black | Size: 9

    These Are In Great Condition Although They Are Used. I Did Not Find Any Scuffs Except A Few On The Heel - Please See The Last Picture. Leather. Size 9. Black. more

    $40.00

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    Madewell Shoes | Madewell Chelsea Boots 6 Tan The Henry Lugsole Suede Leather Pull On Ankle Zip | Color: Tan | Size: 6

    Madewell Shoes | Madewell Chelsea Boots 6 Tan The Henry Lugsole Suede Leather Pull On Ankle Zip | Color: Tan | Size: 6

    Condition: Pre-Owned With Natural Cosmetic Wear Noted, See Photos. Size: 6 Color: Tan Material: Suede Leather Upper Measurements: Shaft Height: 4.5 In Heel Height: 1.75 In Made Of Textured Suede With A Comfy Elasticized Shaft And Grippy Lugsoles, This... more

    $20.00

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    Madewell Shoes | Bnib Madewell Sonia Snakeskin Chelsea Ankle Boots 6 | Color: Black/Tan | Size: 6

    Madewell Shoes | Bnib Madewell Sonia Snakeskin Chelsea Ankle Boots 6 | Color: Black/Tan | Size: 6

    Python Snake Print Heather Natural Leather Chelsea Booties With Almond Toe And Stacked Wooden Heel, Comes With Box 1.75'' Heel 3'' Shaft Pull-On With Elastic Gore Insets Tapered, Stacked Heel Cushioned Footbed Leather Upper Leather Lining more

    $55.00

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    Free People Shoes | Free People Brooks Chelsea Ankle Boots | Color: Green | Size: 6.5

    Free People Shoes | Free People Brooks Chelsea Ankle Boots | Color: Green | Size: 6.5

    Leather Upper Ankle-High Chelsea Boot Shaft Zipper Closure Lightly Cushioned Footbed Lug Outsole Pull-On New Without Box Size 36.5 (6.5) more

    $110.00

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    Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: Black | Size: 8

    Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: Black | Size: 8

    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

    $100.00

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    Madewell Shoes | Madewell Carina Ankle Chelsea Boot Bootie | Color: Brown | Size: 7

    Madewell Shoes | Madewell Carina Ankle Chelsea Boot Bootie | Color: Brown | Size: 7

    Excellent Condition! Size 7 Cognac Color more

    $85.00

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    Gucci Shoes | Gucci Worsh Black Leather Chelsea Ankle Boots | Color: Black | Size: 11

    Gucci Shoes | Gucci Worsh Black Leather Chelsea Ankle Boots | Color: Black | Size: 11

    Only Wore Once To Big It Comes With Original Box And Dust Bags As Well In Great Condition No Scratches Or Marks more

    $950.00

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    Anthropologie Shoes | Anthropologie Silent D Uvika Chelsea Suede Leather Ankle Boots In Honey Brown | Color: Brown/Tan | Size: 7

    Anthropologie Shoes | Anthropologie Silent D Uvika Chelsea Suede Leather Ankle Boots In Honey Brown | Color: Brown/Tan | Size: 7

    Reach New Heights In A Pair Where Elevated Neutrals And A Wedge Heel Take Center Stage. In Great Preowned Condition. Minor Wear To The Outer Sole. One Mark At The Inner Side Gore Panel Of The Left Boot. See Photos. Suede Leather Upper Leather Lining... more

    $75.00

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