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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 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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    Best Seller
    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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    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 10 D)

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

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 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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    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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    Calf Hair Ankle Boots Boots, Ankle Boots

    Calf Hair Ankle Boots Boots, Ankle Boots

    Men's Lidfort Calf Hair Ankle Boots Boots, Ankle Boots - Black - Casual boots Calf hair ankle boots with leather sole and aelastic detail. Colours: Black Composition: 100% calf leather Dimension: UK MEN 25 mm heels MPN: 625CAVALLINONERO. 100% calf... more

    $828.00 $457.00

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    HONEYWELL SERVUS 11003/L Overboots,PVC,Blk/Ylw,4in,L,Sz 11-13,PR

    HONEYWELL SERVUS 11003/L Overboots,PVC,Blk/Ylw,4in,L,Sz 11-13,PR

    Overshoe, Ankle, Footwear Sole Pattern Lug, Toe Type Plain, Black, Fits Shoe Size 11 to 13, Style Number 11003, Boot Height 4 in, Men's, Metatarsal Guard No, Size L, Waterproof Yes, Upper Material PVC, 1 Pair more

    $26.19

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    DUNLOP 8610433 Size 13 Men's Steel Rubber Boot, Black

    DUNLOP 8610433 Size 13 Men's Steel Rubber Boot, Black

    Rubber Boot, Shoe Style Ankle, Toe Type Steel, Footwear Sole Pattern Cleated, Insulated No, Size 13, Footwear Width D, Men's, Boot Height 6 in, Metatarsal Guard No, Waterproof Yes, 1 Pair more

    $43.49

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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

    FREE shipping

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    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

    FREE shipping

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    WIDE FIT Sarah Ankle Boot - black

    WIDE FIT Sarah Ankle Boot - black

    Our Sarah Ankle Boot is an elevated addition to your footwear collection. With its faux leather fabrication, faux fur lining, and front lace-up detail this boot is a stylish piece that brings the perfect finishing touch to your look. Key Features... more

    $109.99 $76.99

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    WIDE FIT Sarah Ankle Boot - black

    WIDE FIT Sarah Ankle Boot - black

    Our Sarah Ankle Boot is an elevated addition to your footwear collection. With its faux leather fabrication, faux fur lining, and front lace-up detail this boot is a stylish piece that brings the perfect finishing touch to your look. Key Features... more

    $109.99 $76.99

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    WIDE FIT Sarah Ankle Boot - black

    WIDE FIT Sarah Ankle Boot - black

    Our Sarah Ankle Boot is an elevated addition to your footwear collection. With its faux leather fabrication, faux fur lining, and front lace-up detail this boot is a stylish piece that brings the perfect finishing touch to your look. Key Features... more

    $109.99 $76.99

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    GEORGIA BOOT GR530 Size 10.5 Men's Chelsea Boot Steel Work Boot, Soggy Brown

    GEORGIA BOOT GR530 Size 10.5 Men's Chelsea Boot Steel Work Boot, Soggy Brown

    Chelsea Boot, Style Family Chelsea Boot, Metatarsal Guard No, ASTM Standards Met Compression (C/75), Impact (I/75), Closure Slip On, Chemical Resisting Sole Yes, Color Soggy Brown, Width M, Gender Men's, Heel Definition Defined Heel, Non Metallic Upper... more

    $132.00

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    Georgia Boot Athens Chelsea Waterproof 5 inch Work Boot - Men's Dark Brown 10 Wide GB00156-100W

    Georgia Boot Athens Chelsea Waterproof 5 inch Work Boot - Men's Dark Brown 10 Wide GB00156-100W

    Georgia Boot Athens Chelsea Waterproof 5 inch Work Boot - Men's Dark Brown 10 Wide GB00156-100W. This men's Chelsea boot's upper is made from a supple full-grain leather and also includes elastic twin gores. The twin gores make the boot easy to slip on... more

    $165.00

    FREE shipping

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    Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 8.5 GB00315-085W

    Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 8.5 GB00315-085W

    Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 8.5 GB00315-085W. The upper is constructed from full-grain SPR leather with twin gore panels and nylon pull tabs. The Georgia Waterproof System will keep your feet protected... more

    $165.00

    FREE shipping

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    Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 12 GB00315-120W

    Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 12 GB00315-120W

    Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 12 GB00315-120W. The upper is constructed from full-grain SPR leather with twin gore panels and nylon pull tabs. The Georgia Waterproof System will keep your feet protected... more

    $165.00

    FREE shipping

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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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    Free People Shoes | Free People Atlas Puffer Chelsea Ankle Boots New | Color: Black | Size: Various

    Free People Shoes | Free People Atlas Puffer Chelsea Ankle Boots New | Color: Black | Size: Various

    Nwob, No Flaws! Free People Atlas Chelsea Puffer Boot, Black These Adorable Boots Sold Out Instantly Everywhere! Multiple Sizes Avail Gleaming Studs And Scalloped Edges Contrast Against The Puffy Profile Of A So-Cool Chelsea Boot Crafted From Leather.... more

    $82.00

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    Free People Shoes | Free People Gold Croc Embossed Beau Western Chelsea Boot Ankle Booties | Color: Gold/Red | Size: Various

    Free People Shoes | Free People Gold Croc Embossed Beau Western Chelsea Boot Ankle Booties | Color: Gold/Red | Size: Various

    So Stunning And Effortlessly Eye-Catching, These Cool Ankle Boots Are Featured In A Western-Style Silhouette And Buttery Soft Leather With Elastic Side Panels, A Minimal Wooden Block Heel, And Bold Pointy Toe. Pull On Style Pull Tabs At Heel Cushioned... more

    $160.00

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    Madewell Shoes | Madewell Leather Ivy Chelsea Ankle Boots. Lug Sole. Light Chestnut Brown. Size 7 | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell Leather Ivy Chelsea Ankle Boots. Lug Sole. Light Chestnut Brown. Size 7 | Color: Brown/Tan | Size: 7

    Gorgeous Madewell Chelsea Ankle Boots. A Beautiful Light Chestnut Color. Lug Soles For Fall, Winter And Spring Weather. Soft Pebbled Leather. Pull-On With Elastic.Size 7. Wore A Couple Of Times, So Leather Creased A Little. They Are Extremely... more

    $81.00

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    Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8 | Color: Black/Cream | Size: 8

    Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8 | Color: Black/Cream | Size: 8

    New With Box Size 38.5 / Us 8.5 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... more

    $170.00

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    Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8.5 | Color: Black/Cream | Size: 8.5

    Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8.5 | Color: Black/Cream | Size: 8.5

    New With Box Size 38.5 / Us 8.5 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... more

    $180.00

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    Free People Shoes | Free People Black Croc Embossed Beau Western Chelsea Boot Ankle Booties | Color: Black | Size: Various

    Free People Shoes | Free People Black Croc Embossed Beau Western Chelsea Boot Ankle Booties | Color: Black | Size: Various

    So Stunning And Effortlessly Eye-Catching, These Cool Ankle Boots Are Featured In A Western-Style Silhouette And Buttery Soft Leather With Elastic Side Panels, A Minimal Wooden Block Heel, And Bold Pointy Toe. Pull On Style Pull Tabs At Heel Cushioned... more

    $160.00

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    Free People Shoes | Free People Boots James Chelsea Ice Leather Light Blue Casual Heeled Ankle | Color: Blue/Gray | Size: 37eu

    Free People Shoes | Free People Boots James Chelsea Ice Leather Light Blue Casual Heeled Ankle | Color: Blue/Gray | Size: 37eu

    Free People Boots James Chelsea Ice Leather Light Blue Casual Heeled Ankle Womens Size: 37 Gorgeous Boots With A Light Blue Tone. Beautiful For Everyday Wear. Light Enough They Kind Of Look Off White So Could Be Pretty Neutral. New Without Tags, Some... more

    $75.00

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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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    J. Crew Shoes | J. Crew Grunge Black Leather “Chelsea” Boots Size 6.5 Streetwear Punk | Color: Black | Size: 6.5

    J. Crew Shoes | J. Crew Grunge Black Leather “ChelseaBoots Size 6.5 Streetwear Punk | Color: Black | Size: 6.5

    Size 6.5, Excellent Condition With Minimal Wear To The Outer Leather And Mild Wear To The Soles-So They Should Be Perfectly Broken In, Sold Out, Msrp $238! Our Chelsea Boots Are Designed In Supple Leather With Elastic Panels At The Ankle, So They're... more

    $100.00

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    Free People Shoes | Free People Monroe White Chelsea Boots Size 39 | Color: Black/White | Size: 8.5

    Free People Shoes | Free People Monroe White Chelsea Boots Size 39 | Color: Black/White | Size: 8.5

    Free People Monroe White Chelsea Boots Size 39 Make A Statement In These So Cool Leather Chelsea Boots Featured In An Ankle-High Style With A Chunky Platform Sole And Bold Elastic Side Accents. Pull-On Style Cushioned Insole Rounded Toe Fit Tip: This... more

    $80.00

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    Free People Shoes | Free People Monroe Chelsea Boots In Brown Leather | Color: Brown | Size: 10

    Free People Shoes | Free People Monroe Chelsea Boots In Brown Leather | Color: Brown | Size: 10

    Make A Statement In These So Cool Leather Chelsea Boots Featured In An Ankle-High Style With A Chunky Platform Sole And Bold Elastic Side Accents. Pull-On Style Cushioned Insole Rounded Toe Fit Tip: This Style Runs True To Size. Fp Collection Artisan... more

    $120.00

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    Free People Shoes | Free People Monroe Chelsea Boot Eu 38 Us 7.5 | Color: Black/Cream | Size: Eu 38 Us 7.5

    Free People Shoes | Free People Monroe Chelsea Boot Eu 38 Us 7.5 | Color: Black/Cream | Size: Eu 38 Us 7.5

    Lightly Worn But In Great Condition! Fast Shipping! Light Marks On Side As Shown In Photos. Make A Statement In These So Cool Leather Chelsea Boots Featured In An Ankle-High Style With A Chunky Platform Sole And Bold Elastic Side Accents. Pull-On Style... more

    $163.00

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    Free People Shoes | Free People Monroe White Chelsea Boots Size 39 | Color: Black/White | Size: 8.5

    Free People Shoes | Free People Monroe White Chelsea Boots Size 39 | Color: Black/White | Size: 8.5

    Free People Monroe White Chelsea Boots Size 39 Make A Statement In These So Cool Leather Chelsea Boots Featured In An Ankle-High Style With A Chunky Platform Sole And Bold Elastic Side Accents. Pull-On Style Cushioned Insole Rounded Toe Fit Tip: This... more

    $82.00

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    Madewell Shoes | Brand New Western Suede Ankle Boots Taupe Madewell 6, Could Be 6.5 | Color: Tan | Size: 6

    Madewell Shoes | Brand New Western Suede Ankle Boots Taupe Madewell 6, Could Be 6.5 | Color: Tan | Size: 6

    Brand New Madewell Western Chelsea Boots In Oiled Suede, Size 6, Could Be 6.5. Walnut Shell. Never Worn. For Reference, I Am Between A 6 And 6h. I Find Madewell Boots To Run A Bit Bigger So Size 6 Works Well For Me. I Usually Wear 37 Or 6h In J Crew... more

    $90.00

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    Anthropologie Shoes | Anthro Madison Harding Blue Velvet Ankle Boots | Color: Blue | Size: 8

    Anthropologie Shoes | Anthro Madison Harding Blue Velvet Ankle Boots | Color: Blue | Size: 8

    To Die For Blue Velvet Booties By Madison Harding. Cool & Unique Party Shoe In A Chelsea Boot/Beatle Boot Shape. Marked 8.5 (My Normal Size) But Run Small So Listing As An 8. Great Condition. Only Worn One Or 2 Times Since They Were Too Small On Me. more

    $34.00

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    Free People Shoes | Free People Vance Double Tab Chelsea Boot - Black | Color: Black | Size: 6

    Free People Shoes | Free People Vance Double Tab Chelsea Boot - Black | Color: Black | Size: 6

    Free People Vance Double Tab Chelsea Boot - Black Worn Twice Perfect Condition, Like New! Patent Leather Top With 1-12” Wood/Rubber Chunky Platform Heel Side Zipper, Easy To Slide On, Ankle Bootie No Box Size Us 6 / Eu 36 Made In Spain Thank You So... more

    $95.00

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    Free People Shoes | Free Peoples Lug Sole Chunky Heel Ankle Bootie James Chelsea White Leather New | Color: White | Size: Various

    Free People Shoes | Free Peoples Lug Sole Chunky Heel Ankle Bootie James Chelsea White Leather New | Color: White | Size: Various

    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 Insole... more

    $150.00

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    More information about Men's Shoes

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