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    Best Seller
    Madewell Shoes | New Madewell The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: Various

    Madewell Shoes | New Madewell The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: Various

    New Without Box. Line On Inside Label To Prevent In Store Returns. Color: Warm Cinnamon Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like... more

    $118.00

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    Kate Spade Shoes | Kate Spade Chelsea Rain Boot | Color: Black/Gold | Size: 8

    Kate Spade Shoes | Kate Spade Chelsea Rain Boot | Color: Black/Gold | Size: 8

    Excellent Condition, Very Gently Used Rain Boot By Kate Spade. These Are Black And Gold With Cute Spade/Bow On Back. Minimal Wear To Soles. I Just Never Worn Them. Stretch Side For Easy On And Off. more

    $65.00

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    Best Seller
    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot-Size 6.5 | Color: Brown | Size: 6.5

    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot-Size 6.5 | Color: Brown | Size: 6.5

    These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 6" Shaft Height. 1 1/2" Heel Height. Leather Upper. Leather... more

    $100.00

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    Vance Co. Shoes Vance Co. Marshall Chelsea Boot - Grey - 10.5

    Vance Co. Shoes Vance Co. Marshall Chelsea Boot - Grey - 10.5

    This boot by Vance Co. will work overtime for you, as you wear it to the office, the store, and everywhere else. The Marshall is an iconic Chelsea silhouette with a pull-tab and stretch goring on either side. This wear-it-everywhere look is made with... more

    $69.99

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    Vance Co. Shoes Vance Co. Marshall Wide Width Chelsea Boot - Brown - 13

    Vance Co. Shoes Vance Co. Marshall Wide Width Chelsea Boot - Brown - 13

    This chelsea boot by Vance Co. will work overtime for you, as you wear it to work, while running errands, and everywhere else. The Marshall is an iconic round-toe silhouette with a wide-width footbed and stretch gore on either side for the perfect fit.... more

    $69.99

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    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 11.5

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 11.5

    Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more

    $69.99

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    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Brown/Tan | Size: 7

    Moving Soon So I Really Need To Clear Out The Closet! Gently Worn Madewell Boots In Cognac Color. Totally Love These Boots But I Am Never Reaching For Them These Days. From Madewell: Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared... more

    $50.00

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    Free People Shoes | Free People James Chelsea Mustard Yellow Suede Platform Boots Size 39 | Color: Black/Yellow | Size: 8.5

    Free People Shoes | Free People James Chelsea Mustard Yellow Suede Platform Boots Size 39 | Color: Black/Yellow | Size: 8.5

    Free People James Chelsea Mustard Yellow Suede Platform Boots Size 39 (Us Size 8.5) *Good Used Condition : See Photos For Minimal Signs Of Wear : Couple Small Spots Side Of One Of The Boots. *Quality Leather Upper With Black Stretch *Pretty Color :... more

    $80.00

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    Madewell Shoes | New Madewell Size 6 Wyckoff Chelsea Lugsole Boots In True Black Leather | Color: Black | Size: 6

    Madewell Shoes | New Madewell Size 6 Wyckoff Chelsea Lugsole Boots In True Black Leather | Color: Black | Size: 6

    New Without Box. Store Display Models And May Have Minor Shelf/Try On Wear. See Pics. Line On Inside Label To Prevent In Store Returns. Size 6 Color: True Black Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And... more

    $118.00

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    Madewell Shoes | Madewell Size 6 The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: 6

    Madewell Shoes | Madewell Size 6 The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: 6

    New With Defects. Store Display Models And Have A Couple Areas Of Discoloration In The Leather - See Pics. Line On Inside Label To Prevent In Store Returns. Size 6 Color: Warm Cinnamon Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores... more

    $74.00

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    Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

    Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

    Tan Leather With Elastic Stretch On Both Side For Easy Slip On Round Toe Leather Sole Preowned But In Good Condition more

    $65.00

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    J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

    J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

    J Crew Cognac Brown Leather Chelsea Boots With Stretch Panels For Easy Pull-On. Tag Size 8. Fits 7.5-8 In My Opinion. Style Eo824 Preowned. Shows Signs Of Wear Including Scuffs On Toes, Wear On Back Heels, Wear On Bottoms Of Soles, Creasing In Midfoot... more

    $50.00

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    Madewell Shoes | Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 | Color: Brown/Tan | Size: 7

    Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 Brand: Madewell Size: 7 Color: Tan And Brown Pattern: Leopard Material: Leather Condition: Preloved, In Good Condition, Stretch Band Shows Minimal Features: Slip On Closure... more

    $125.00

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    Free People Shoes | Fp & Faryl Robyn Collaboration Janice Chelsea Boot | Color: Black/Pink | Size: 9

    Free People Shoes | Fp & Faryl Robyn Collaboration Janice Chelsea Boot | Color: Black/Pink | Size: 9

    So Unique Chelsea Boot From Fp And Faryl Robyn...Worn A Couple Times And In Excellent Preowned Condition. Only Wear Is Shown On Bottom Of Shoe And That’s Because We Have A Very Pebbly Path Heals Are In Great Condition And Leather’s Still Stiff And... more

    $80.00

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    Madewell Shoes | Https://Www.Madewell.Com/The-Benning-Chelsea-Boot-Nn017.Html | Color: Brown | Size: 9

    Madewell Shoes | Https://Www.Madewell.Com/The-Benning-Chelsea-Boot-Nn017.Html | Color: Brown | Size: 9

    Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. Leather Upper. Leather Lining. Man-Made Sole. Do Well:... more

    $80.00

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    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Chocolate Leather Size 11 Nn020 | Color: Brown | Size: 11

    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Chocolate Leather Size 11 Nn020 | Color: Brown | Size: 11

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know.6" Shaft Height1 1/2"... more

    $78.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 6

    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 6

    Size 6 No Box Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. When You Select Your Size, "H"... more

    $60.00

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    Free People Shoes | Free People Brooks Lug Sole Chelsea Boot | Color: Black | Size: 8

    Free People Shoes | Free People Brooks Lug Sole Chelsea Boot | Color: Black | Size: 8

    Free People Brooks Lug Sole Chelsea Boot In Good Pre Owned Condition. Some Parts Can Use A Brushing As Can Be Expected With Suede. Some Very Minimal Creasing On Ankle Part. Please See All Pictures For Wear. Minor Wear On Soles. Features A Super-Chunky... more

    $105.00

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    J. Crew Shoes | J. Crew Pull On Chelsea Boots In Desert Sand Suede Size 8 And Size 9 Nib | Color: Tan | Size: Various

    J. Crew Shoes | J. Crew Pull On Chelsea Boots In Desert Sand Suede Size 8 And Size 9 Nib | Color: Tan | Size: Various

    J. Crew Beige Suede Pull On Chelsea Boots Nib Size: 8 And 9 Color: Desert Sand With Black Condition: New In Box Content: Suede Upper Leather Lining Synthetic Sole Pull On Styling Black Stretch Panels On Side Walkable Chelsea Boots In Soft Suede With A... more

    $124.00

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    Madewell Shoes | Madewell Like New The Chelsea Rain Boot | Color: Black | Size: 5

    Madewell Shoes | Madewell Like New The Chelsea Rain Boot | Color: Black | Size: 5

    Madewell Like New The Chelsea Rain Boot Like New Condition No Box Rudder Boot Chelsea Style Stretch Sides Black Size 5 more

    $45.00

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    Madewell Shoes | Madewell The Benning Chelsea Boot Sz 6 Nn017 | Color: Black | Size: 6

    Madewell Shoes | Madewell The Benning Chelsea Boot Sz 6 Nn017 | Color: Black | Size: 6

    Boots Are New Without Box, Display Item, So The Bottoms Are A Tad Dirty Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On... more

    $80.00

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    Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

    Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. When You Select Your... more

    $78.00

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    Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

    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

    $45.00

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    J. Crew Shoes | J. Crew Pull-On Chelsea Suede Boots In Desert Sand | Color: Black/Tan | Size: 9

    J. Crew Shoes | J. Crew Pull-On Chelsea Suede Boots In Desert Sand | Color: Black/Tan | Size: 9

    J. Crew Pull-On Chelsea Suede Boots In Desert Sand Feature A Leather Lining, Soft Suede With A Stretchy Side Panel, Just Pull 'Em On And Go! You'll Want To Reach For Our Easy Oh-So-Walkable Chelsea Boots Everyday. Item Does Not Include The Original Box. more

    $150.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5

    Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5

    Madewell Leather Ankle Boots Gently Worn Elastic Stretch On Interior And Exterior Side Ankle Minor Scuffing On Left Shoe Shown In Photo more

    $47.00

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    Anthropologie Shoes | Cecelia New York Chelsea Boots - Black | Color: Black | Size: 8

    Anthropologie Shoes | Cecelia New York Chelsea Boots - Black | Color: Black | Size: 8

    New In Box, Anthropologie, Cecelia Black Chelsea Boots. Pull On Styling (Stretch Goring Side Panels) Suede Upper Leather Insole Eva Sole & Heel 2¼" Heel 1" Platform more

    $175.00

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    Coach Shoes | Coach Bowery Beadchain Chelsea Boots Black - 8 | Color: Black | Size: 8

    Coach Shoes | Coach Bowery Beadchain Chelsea Boots Black - 8 | Color: Black | Size: 8

    Gorgeous Bowery Beadchain Chelsea Boots From Coach. Black Leather With Beadchain Detailing Around The Ankle. Pull On Style With Stretch Panels For A Comfortable Fit. Essential Style For Every Day Wear. New In Box. Size 8b more

    $125.00

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    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot Sz 9.5 Nn020 | Color: Black/White | Size: 9.5

    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot Sz 9.5 Nn020 | Color: Black/White | Size: 9.5

    New Without Box, Some Very Subtle Black Marks On Boots Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like... more

    $95.00

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    J. Crew Shoes | J. Crew Pull On Chelsea Boots In Desert Sand Suede Size 9 New Without Box | Color: Tan | Size: 9

    J. Crew Shoes | J. Crew Pull On Chelsea Boots In Desert Sand Suede Size 9 New Without Box | Color: Tan | Size: 9

    J. Crew Beige Suede Pull On Chelsea Boots Size 9 Color: Desert Sand With Black Condition: New Without Box Suede Upper Leather Lining Synthetic Sole Pull On Black Stretch Panels On Side Walkable Chelsea Boots In Soft Suede With A Stretchy Side Panel more

    $36.00

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    J. Crew Shoes | J. Crew Pull On Chelsea Boots In Desert Sand Suede Size 8 And Size 9 Nib | Color: Tan | Size: Various

    J. Crew Shoes | J. Crew Pull On Chelsea Boots In Desert Sand Suede Size 8 And Size 9 Nib | Color: Tan | Size: Various

    J. Crew Beige Suede Pull On Chelsea Boots Nib Size: 8 And 9 Color: Desert Sand With Black Condition: New In Box Content: Suede Upper Leather Lining Synthetic Sole Pull On Styling Black Stretch Panels On Side Walkable Chelsea Boots In Soft Suede With A... more

    $99.00

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    Tory Burch Shoes | $520 Tory Burch Expedition Chelsea Boot Chunky Square Toe Black 8 (Me10) | Color: Black | Size: 8

    Tory Burch Shoes | $520 Tory Burch Expedition Chelsea Boot Chunky Square Toe Black 8 (Me10) | Color: Black | Size: 8

    Floor Model And Tried On Excellent Back Tabs Are Missing - Please See Pictures!! Size Info True To Size. Details & Care A Rubber Toe Caps Off This Expedition-Seeking Leather Boot Crafted With Stretchy Side Goring And Balanced On A Block Heel For Steady... more

    $270.00

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    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Nib Free People James Chelsea Ankle Boots Side Zip Closure Stretch Side Panels For Easy On Cushion Footbed Color Is White But Looks More Like A Cream Color Leather Uppers 6” Shaft Height 3.5” Chunky Heel 1” Platform more

    $85.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 9

    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 9

    Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. When You Select Your Size, "H" Equals A Half... more

    $100.00

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    Free People Shoes | Free People Chelsea Textile Atlas Boots Blue Kilm Western Ankle Scallop 40 | Color: Blue | Size: 40eu

    Free People Shoes | Free People Chelsea Textile Atlas Boots Blue Kilm Western Ankle Scallop 40 | Color: Blue | Size: 40eu

    Excellent Condition ... No Flaws!! Bundle And Save 20%... Free Shipping On All Bundles! ~ Offers Welcome! ~ Fast Shipping! ~ For Offers European Size 40 Appreciate Your Wonderful Sense Of Style And Make A Statement In These Jaw-Dropping Chelsea Boots... more

    $98.00

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    Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

    Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

    A Contemporary Spin On The Classic Chelsea Style, These Timeless Ankle-Covering Boots Feature A Chunky Sole For An Exaggerated Look. A Neutral Boot To Pop Any Outfit Fp Collection Color Chalk Artisan Crafted From Fine Leathers And Premium Materials, Fp... more

    $25.00

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    Madewell Shoes | Madewell The Ainsley Chelsea Boot | Color: Black | Size: 7.5

    Madewell Shoes | Madewell The Ainsley Chelsea Boot | Color: Black | Size: 7.5

    Love These Boots, But Only Wore Twice - They’re Too Narrow For My Feet In This Size.* Both Casual And Stylish Leather Booties, With Cloudlift Lite Padding. *They Run Narrow, But Will Stretch With Wear. Go Up A Size If You Have A Wider Foot Or Want To... more

    $90.00

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    Coach Shoes | Coach Elijah Chelsea Boots | Color: Red | Size: 8

    Coach Shoes | Coach Elijah Chelsea Boots | Color: Red | Size: 8

    Coach Elijah Chelsea Boots In Good Used Condition. Has Creases From Normal Wear. Polished Calf Leather Gives This Tomboyish Boot A Rich Sheen, While The Saddle-Colored Stripe On The Sole Is A Nod To Heritage Coach(Tm) Craftsmanship. Fashion Meets... more

    $95.00

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    Free People Shoes | Free People Atlas Textile Chelsea Ankle Boots | Color: Black/Blue | Size: 38eu

    Free People Shoes | Free People Atlas Textile Chelsea Ankle Boots | Color: Black/Blue | Size: 38eu

    Rounded Toes ~ Ankle Height Shaft ~ Dual/Two Stretchy Gore Panels On The Sides Of The Ankle Shafts ~ Leather Panels On Toes And Heels ... With Scalloped Leather Trims Trimming The Gore/Stretch Panels ~ Woven Textile Panels On Top Of The Foot And On The... more

    $72.00

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    Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

    Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

    Brand - Free People Size - Eu 39.5 / Us 9.5 Excellent Preowned Condition Ankle, Chelsea, Studded Trim, Scalloped Lace Trim, Pull On, Side Stretch, Suede, Leather, Round Toe, Comfortable, Hiking, Causal, Winter, Fall, Combat, Booties more

    $85.00

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    Michael Kors Shoes | Michael Kors Leather Chelsea Wedge Boot | Color: Black | Size: 7.5

    Michael Kors Shoes | Michael Kors Leather Chelsea Wedge Boot | Color: Black | Size: 7.5

    Michael Kors Black Leather Bootie! Heel Is Around 3 1/2 Inches. Excellent Condition. Slight Scuffs On Heel And Elastic Slight Stretch At Top Of Boot As Shown In Pictures. more

    $75.00

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    More information about Men's Shoes

    Best prices on Muck boots outscape chelsea boot, Stretchable, Shoes in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.