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    Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

    Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

    Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. more

    $50.00

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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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    Best Seller
    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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    Kathleen Lug Sole Block Heel Chelsea Boot - Black - Madewell Boots

    Kathleen Lug Sole Block Heel Chelsea Boot - Black - Madewell Boots

    Women's Madewell Kathleen Lug Sole Block Heel Chelsea Boot - Black - Ankle boots A stacked block heel and lug sole add a rugged contrast to a classic Chelsea boot made from smooth leather. more

    $198.00

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    The Wyckoff Chelsea Lugsole Boot - Black - Madewell Boots

    The Wyckoff Chelsea Lugsole Boot - Black - Madewell Boots

    Women's Madewell The Wyckoff Chelsea Lugsole Boot - Black - Ankle boots Ready for all your supercute fall 'fits, this leather Chelsea boot has a stretchy gore and a wear-all-day-everywhere chunky lugsole. And, cushiness alert: MWL Cloudlift Lite... more

    $198.00

    FREE shipping

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    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 D)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 D)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 EE)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 EE)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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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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    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 557201

    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 557201

    The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

    $229.95

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    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 168992

    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 168992

    The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

    $229.95

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    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 562692

    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 562692

    The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

    $229.95

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    Madewell Shoes | Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 | Color: Brown | Size: 10

    Madewell Shoes | Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 | Color: Brown | Size: 10

    Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 New Without Tag Shoe Is Store Return And May Have Minor Blemish more

    $95.00

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    Madewell Shoes | Madewell Chelsea Lonny Ankle Boots | Color: Black | Size: 8.5

    Madewell Shoes | Madewell Chelsea Lonny Ankle Boots | Color: Black | Size: 8.5

    Madewell Chelsea Lonny Ankle Boots Size 8.5 Used In Great Condition Madewell “The Lonny” Boot. Black Leather Ankle Boot. Stacked Heel, Strap Around Ankle Is Held In Place With Stylish Gold Pin/Ball. Chelsea Boot Style Elastic Sides. Heel Height Is 3... more

    $32.00

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    Madewell Shoes | Classic Madewell Chelsea Ankle Boot | Color: Brown | Size: 7.5

    Madewell Shoes | Classic Madewell Chelsea Ankle Boot | Color: Brown | Size: 7.5

    Reposhing This Item I Purchased From @Amplifyart7. Loved It, But Ready To Rotate For Something New. Small Stain On Left Toe. more

    $30.00

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    Madewell Shoes | Madewell Low Ankle Chelsea Boots Snakeskin Leather Size 6.5 Style M3463 | Color: Black/Cream | Size: 6.5

    Madewell Shoes | Madewell Low Ankle Chelsea Boots Snakeskin Leather Size 6.5 Style M3463 | Color: Black/Cream | Size: 6.5

    Madewell Low Ankle Chelsea Boots Snakeskin Leather Size 6.5 In Excellent Condition, No Flaws more

    $50.00

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    Madewell Shoes | Madewell Regan Taupe Suede Leather Stacked Heel Ankle Chelsea Boots Sz 9.5 | Color: Gray/Tan | Size: 9.5

    Madewell Shoes | Madewell Regan Taupe Suede Leather Stacked Heel Ankle Chelsea Boots Sz 9.5 | Color: Gray/Tan | Size: 9.5

    Taupe Suede Heeled Chelsea Boots From Madewell. Worn Only A Couple Times And Still In Excellent Condition. Very Cute And Great For Fall! Size 9.5 Please Let Me Know If You Have Any Questions Or Would Like Additional Photos. more

    $75.00

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    Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Suede Ankle Booties Western Oxford 8 | Color: Brown | Size: 8

    Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Suede Ankle Booties Western Oxford 8 | Color: Brown | Size: 8

    Madewell The Grayson Brogue Chelsea Boot. Saddle Brown Suede Leather Ankle Booties. Rustic Footwear With Western Kick. Wingtip Oxford Detailing, Stretch Side Gussets, Back Pull Tab To Help With Slide On / Slip On Styling. Cushioned Insoles, Leather... more

    $79.00

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    Madewell Shoes | Brand New Madewell Chelsea Ankle Boots | Color: Brown | Size: 7.5

    Madewell Shoes | Brand New Madewell Chelsea Ankle Boots | Color: Brown | Size: 7.5

    Brand New Madewell Pull-On Ankle Chelsea Boots Never Worn. Brand New With Original Tag And Shoe Box. Classical Ankle Chelsea Boots In Size 7.5. Color Is Dark Cabernet. more

    $64.00

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    Madewell Shoes | Madewell The Ainsley Brown Leather Chelsea Pull On Ankle Boots Size 8 | Color: Brown/Tan | Size: 8

    Madewell Shoes | Madewell The Ainsley Brown Leather Chelsea Pull On Ankle Boots Size 8 | Color: Brown/Tan | Size: 8

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

    $35.00

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    Madewell Shoes | Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim | Color: Black | Size: 9

    Madewell Shoes | Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim | Color: Black | Size: 9

    Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim 1 1/2” Heel 4 1/2” Shaft Height Leather, Suede Upper Man-Made Sole Style # Mb834 Slight Scuffing On Rim Of Front Toes But Not Noticeable When Wearing more

    $32.00

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    Madewell Shoes | Madewell Ainsley Black Leather Chelsea Pull On Ankle Boots Size 9.5 | Color: Black | Size: 9.5

    Madewell Shoes | Madewell Ainsley Black Leather Chelsea Pull On Ankle Boots Size 9.5 | Color: Black | Size: 9.5

    Black Leather Upper Chelsea Side Panels Ankle Height Really Great Condition Gently Worn more

    $36.00

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    Madewell Shoes | Madewell Carina Chelsea Ankle Boots 6.5 | Color: Tan | Size: 6.5

    Madewell Shoes | Madewell Carina Chelsea Ankle Boots 6.5 | Color: Tan | Size: 6.5

    Questions? Leave A Comment Below! more

    $61.00

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    Madewell Shoes | Madewell Bryce Black Suede Chelsea Ankle Boot Size 9.5 | Color: Black | Size: 9.5

    Madewell Shoes | Madewell Bryce Black Suede Chelsea Ankle Boot Size 9.5 | Color: Black | Size: 9.5

    Madewell Black Ankle Boot Size: 9.5 Style Name: Byrce Style: M4674 Msrp: Was $158 Condition: Pre-Owned In Excellent Condition. Upper Suede Is In Pristine Condition, Outsole Has Minor Wear Heel: 3.25" Block Heel Features: Leather Upper And Lining,... more

    $69.00

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    Madewell Shoes | Madewell Brown Leather Chelsea Ankle Boots | Color: Brown | Size: 7

    Madewell Shoes | Madewell Brown Leather Chelsea Ankle Boots | Color: Brown | Size: 7

    Worn A Handful Of Times, In Fabulous Condition, Perfect For Fall more

    $45.00

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    Madewell Shoes | Madewell The Grayson Brogue Chelsea Ankle Boot Tan | Color: Tan | Size: 7.5

    Madewell Shoes | Madewell The Grayson Brogue Chelsea Ankle Boot Tan | Color: Tan | Size: 7.5

    Our Design Team Took Age-Old Western Boot Details, A Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforations And Cut Them Low On The Ankle To Make Your Legs Look Even Longer A Pull-On Style For In-Between Weather Extra Layer Of Padding To Make Them... more

    $88.00

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    Madewell Shoes | Madewell Walker Chelsea Olive Green Suede 2” Heeled Ankle Boot - Size 9 | Color: Green | Size: 9

    Madewell Shoes | Madewell Walker Chelsea Olive Green Suede 2” Heeled Ankle Boot - Size 9 | Color: Green | Size: 9

    Madewell Walker Chelsea Suede Ankle Boot - Size 9 Retail Price $$188.00 + Tax In Supersoft Suede, These Sleek Chelsea Boots Give A Low-Key Nod To Timeless '60s Styles. The Not-Too-High Heel Is Made For Adventuring Day Or Night. 2" Heel. Suede Upper.... more

    $75.00

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    Madewell Shoes | Madewell Sonia Chelsea Low Ankle Boots Snake Embossed Leather Natural Size 6 | Color: Black/Tan | Size: 6

    Madewell Shoes | Madewell Sonia Chelsea Low Ankle Boots Snake Embossed Leather Natural Size 6 | Color: Black/Tan | Size: 6

    Madewell Leather Chelsea Boots Embossed Snake Size 6 Excellent Used Condition, No Major Flaws Slip On Style Low Ankle Height Short Block Heel Slightly Pointed Toe Leather Upper/Lining/Sock Synthetic Sole more

    $40.00

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    Madewell Shoes | Madewell The Grayson Brogue Chelsea Bootie Western Cut Suede Ankle Boots | Color: White | Size: 7

    Madewell Shoes | Madewell The Grayson Brogue Chelsea Bootie Western Cut Suede Ankle Boots | Color: White | Size: 7

    Size 8 In Good Condition And I Didn't Find Any Flaws more

    $60.00

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    Madewell Shoes | Madewell Walker Chelsea Boot Ankle Booties In Black Suede Size 9 | Color: Black | Size: 9

    Madewell Shoes | Madewell Walker Chelsea Boot Ankle Booties In Black Suede Size 9 | Color: Black | Size: 9

    Madewell Booties In Very Good Used Condition Black Suede Is Soft And Clean And Ready For A Fall Or Winter Of Wear! Size Women’s 9 Slip On, Pull On, Casual, Dressy, Classy, Classic, Minimalist, Office, Neutral, Versatile, Capsule Piece, more

    $75.00

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    Madewell Shoes | Madewell Chelsea Snake Embossed Ankle Boots New! | Color: Red | Size: 8.5

    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

    $68.00

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    Madewell Shoes | Madewell 1937 Footwear Chelsea Leather Ankle Boot | Color: Brown | Size: 8.5

    Madewell Shoes | Madewell 1937 Footwear Chelsea Leather Ankle Boot | Color: Brown | Size: 8.5

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

    $25.00

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    Madewell Shoes | Madewell The Kat Camel Tan Suede Block Heel Chelsea Ankle Boots 8.5m | Color: Tan | Size: 8.5

    Madewell Shoes | Madewell The Kat Camel Tan Suede Block Heel Chelsea Ankle Boots 8.5m | Color: Tan | Size: 8.5

    Size 8.5m. Camel Tan Suede. 2.5" Block Heel. Slip On. Great Condition. more

    $55.00

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    Madewell Shoes | Madewell - The Grayson Brogue Tan Suede Chelsea Western Ankle Boot Size 8.5 | Color: Brown/Tan | Size: 8.5

    Madewell Shoes | Madewell - The Grayson Brogue Tan Suede Chelsea Western Ankle Boot Size 8.5 | Color: Brown/Tan | Size: 8.5

    Madewell - The Grayson Brogue Chelsea Tan Suede Ankle Boot Size 8.5 Excellent Condition Small Scratches On Bottom Of Boot Size 8.5 Heel Height - 2.5 Western Boot Details Stacked Raw Leather Heels Pointy Toe Pull On Style 3” Shaft Height Suede Upper... more

    $89.00

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    Madewell Shoes | Madewell Regan Black Leather Chelsea Pull On Ankle Boot - Size 9.5 Cloud J8307 | Color: Black | Size: 9.5

    Madewell Shoes | Madewell Regan Black Leather Chelsea Pull On Ankle Boot - Size 9.5 Cloud J8307 | Color: Black | Size: 9.5

    Madewell Regan Black Leather Chelsea Pull On Ankle Boot Size 9.5 Heel = 2.75". Style J8307 Modern Style Chelsea Boot In Black Leather, Looks Great With Anything! Comfortable Block Heel And Easy Pull On Style. Msrp $178. Gently Used Condition With Minor... more

    $110.00

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    Madewell Shoes | Madewell Bryce Suede Chelsea Black Ankle Boot | Color: Black | Size: 9

    Madewell Shoes | Madewell Bryce Suede Chelsea Black Ankle Boot | Color: Black | Size: 9

    Reposhing This Item I Purchased From @Sealedmanila. Loved It, But Ready To Rotate For Something New. Worn A Few Times! Thought I Could Use Suede Instead Of Leather But It Didn’t Work With The Outfit. Questions? Leave A Comment Below! more

    $50.00

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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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    Madewell Shoes | Madewell Ryan Black Leather Chelsea Ankle Boot Size 9.5 | Color: Black | Size: 9.5

    Madewell Shoes | Madewell Ryan Black Leather Chelsea Ankle Boot Size 9.5 | Color: Black | Size: 9.5

    Madewell Black Ankle Boot Size: 9.5 Style Name: Ryan Style #: E2331 Msrp: Was $158 Condition: Pre-Owned In Excellent Condition. The Upper Leather Is In Pristine Condition, Lower Has Normal Wear And Tear. Heel: 3.25" Features: Slip On Styling With... more

    $66.00

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    Madewell Shoes | Madewell Regan Chelsea Ankle Boot In English Saddle Size 7.5 | Color: Brown | Size: 7.5

    Madewell Shoes | Madewell Regan Chelsea Ankle Boot In English Saddle Size 7.5 | Color: Brown | Size: 7.5

    Madewell Regan Chelsea Ankle Boot In English Saddle. Made Of Rich Leather, These Cool Pull-On Boots Have Block Heels For A Little Extra Height. Color: Brown Size 7.5 Condition : Preloved, No Rips, Holes Or Tears. Normal Signs Of Wear. No Modeling... more

    $70.00

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    Madewell Shoes | Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 | Color: Gray | Size: 9

    Madewell Shoes | Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 | Color: Gray | Size: 9

    Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 Pointed Toe Very Small Heeled Sole, Less Than 1" Pull On Style Stretch Panel For Ease Getting On And Off Great Condition, A Few Tiny Marks As Shown more

    $100.00

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