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    Best Seller
    Madewell Shoes | Madewell Side-Gore Chelsea Boots In Leather | Color: Brown | Size: 9

    Madewell Shoes | Madewell Side-Gore Chelsea Boots In Leather | Color: Brown | Size: 9

    Only Worn 2 Times. In Great Condition. Color -English Saddle. more

    $85.00

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    Free People Shoes | Free People Charm Double V-Cutout Chelsea Boots, Camel Suede - Nib | Color: Brown/Tan | Size: Various

    Free People Shoes | Free People Charm Double V-Cutout Chelsea Boots, Camel Suede - Nib | Color: Brown/Tan | Size: Various

    Classically Cool Pointed Toe Leather Ankle Boots Features A Pull-On Style With V-Cutouts At Both Sides And A Stacked Heel. Features: * Buttery Soft Suede Leather * Pointed Toes * Leather Lining * Cushioned Leather Insole * Imported Measurements (Based... more

    $148.00

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    Best Seller
    Gucci Shoes | Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots | Color: Black | Size: 10.5

    Gucci Shoes | Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots | Color: Black | Size: 10.5

    Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots Size 40.5 Black Leather Matelasse Leather Double G 2 Inches Made In Italy Comes With Original Box, Tags, Dust Bags, Booklets more

    $950.00

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    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Blue - 10.5

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Blue - 10.5

    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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    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 10.5

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 10.5

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

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Blue - 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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    Free People Shoes | Free People Vance Double Tab Chelsea Boot Crackle Size Eu 36 Us 6 | Color: Blue | Size: 6

    Free People Shoes | Free People Vance Double Tab Chelsea Boot Crackle Size Eu 36 Us 6 | Color: Blue | Size: 6

    Free People Vance Double Tab Chelsea Boot Crackle Patent Leather Navy Eu 36 Us 6 Retail $298 New W/O Box-Sole Marked To Prevent Return To Retail Store Wood Platform Leather Upper Ankle-High Chelsea Boot Shaft Closed Round Toe Pull-On Style With Front... more

    $224.00

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    Free People Shoes | Free People Navy Blue Vance Double Tab Cracked Patent Leather Chelsea Boot 38 8 | Color: Blue | Size: 8

    Free People Shoes | Free People Navy Blue Vance Double Tab Cracked Patent Leather Chelsea Boot 38 8 | Color: Blue | Size: 8

    Free People Vance Double Tab Chelsea Boot Crackle Patent Leather Navy Blue Inside Zipper * Brown Trim * Wood Platform New Without Box * Size: 38/ 8 Retail Price: $298.00 2.25" Rubber Lug Heel more

    $100.00

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    Free People Shoes | Free People Santa Fe Arlo Chelsea Boots Croc Embossed Leather Boots Croc Nwob | Color: Brown/Tan | Size: 7

    Free People Shoes | Free People Santa Fe Arlo Chelsea Boots Croc Embossed Leather Boots Croc Nwob | Color: Brown/Tan | Size: 7

    An Elastic Gore Inset Makes For Easy-On Styling In This Leather Bootie That'll Carry You Through Every Season. Leather And Textile Upper/Textile Lining/Rubber Sole Made In Spain more

    $118.00

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    Free People Shoes | Free People Santa Fe Arlo Chelsea Boots Croc Embossed Leather Boots | Color: Black | Size: Various

    Free People Shoes | Free People Santa Fe Arlo Chelsea Boots Croc Embossed Leather Boots | Color: Black | Size: Various

    An Elastic Gore Inset Makes For Easy-On Styling In This Leather Bootie That'll Carry You Through Every Season. Leather And Textile Upper/Textile Lining/Rubber Sole Eu Size 38 And 38.5 Nwob Location Bin 36 more

    $100.00

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    Free People Shoes | Free People Santa Fe Arlo Chelsea Boots Croc Embossed Leather Boots Dust Storm | Color: Gray | Size: 8.5

    Free People Shoes | Free People Santa Fe Arlo Chelsea Boots Croc Embossed Leather Boots Dust Storm | Color: Gray | Size: 8.5

    An Elastic Gore Inset Makes For Easy-On Styling In This Leather Bootie That'll Carry You Through Every Season. Leather And Textile Upper/Textile Lining/Rubber Sole Eu Size 38.5 Nwob Location Bin 36 more

    $100.00

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    Madewell Shoes | Madewell Sonia Low Leather Chelsea Boot Snakeskin Print Nwt (New With Box) | Color: Black/Brown | Size: 9.5

    Madewell Shoes | Madewell Sonia Low Leather Chelsea Boot Snakeskin Print Nwt (New With Box) | Color: Black/Brown | Size: 9.5

    Ankle Booties With 1 3/4” Stacked Heel, Leather Upper With Pull-On Elastic Gore, Cushioned Footbed more

    $60.00

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    Burberry Shoes | Burberry Men’s Tanner Check Pull On Wingtip Chelsea Boots Size 11 (44) | Color: Brown | Size: 11

    Burberry Shoes | Burberry Men’s Tanner Check Pull On Wingtip Chelsea Boots Size 11 (44) | Color: Brown | Size: 11

    These Burberry Boots Feature Elastic Gores For A Flexible Fit,A Pull Tap At Heel,A Decorative Broguing At Upper And Backstay,A Check Pattern At Gores,Leather Upper,Lining And Sole.Fits True To Size.Made In Italy.Authenticity Guarantee By Poshmark For... more

    $875.00

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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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    Madewell Shoes | Madewell Ivy Chelsea Brown Croc Ankle Boots 5 | Color: Brown/Tan | Size: 5

    Madewell Shoes | Madewell Ivy Chelsea Brown Croc Ankle Boots 5 | Color: Brown/Tan | Size: 5

    In Overall Great Condition. Smoke Free Home. Size: 5 Brown Croc Pull On Leather Casual Neutral Elastic Side Gore more

    $75.00

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    Free People Shoes | Free People | James Heeled Lug Sole Chelsea Boot Black Size 39 | Color: Black/Tan | Size: 9

    Free People Shoes | Free People | James Heeled Lug Sole Chelsea Boot Black Size 39 | Color: Black/Tan | Size: 9

    Free People James Chelsea Boot Lug Sole And Chunky Heel Elastic Gore Side Zipper Leather Upper Muted Black With Light Tan Sole A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets... more

    $60.00

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    Coach Shoes | Coach Chelsea Leather Ankle Boot | Color: Green | Size: 10

    Coach Shoes | Coach Chelsea Leather Ankle Boot | Color: Green | Size: 10

    Leather Upper Man-Made Leather Lining And Footbed Leather Outsole Pull On Side Gore In Darker Green Nwot. Box Not Included. Smells Of Leather. No Flaws. Fast Shipping. more

    $118.00

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    Madewell Shoes | Madewell Snake Print Leather Chelsea Ankle Boot 9m | Color: Brown/Tan | Size: 9

    Madewell Shoes | Madewell Snake Print Leather Chelsea Ankle Boot 9m | Color: Brown/Tan | Size: 9

    New Nordstrom's Rack Store Display, Madewell's Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To This Chelsea Boot That Is Versatile And Comfortable Enough To Go From Work-To-Weekend Style. -- Pull-On Style With Elastic Gore Insets -... more

    $49.00

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    Madewell Shoes | Madewell Wyckoff Chelsea Suede Lugsole Boot | Color: Black/Gray | Size: 8

    Madewell Shoes | Madewell Wyckoff Chelsea Suede Lugsole Boot | Color: Black/Gray | Size: 8

    New Without Box. Ready For All Your Supercute Fall Fits, These Suede Chelsea Boots Have Stretchy Gores And Wear-Alllday-Everywhere Chunky Lugsoles. Suede Upper. Leather Lining. Man-Made Sole. more

    $125.00

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    Free People Shoes | Free People James Chelsea Boots Size 39cream | Color: Black/Cream | Size: 9

    Free People Shoes | Free People James Chelsea Boots Size 39cream | Color: Black/Cream | Size: 9

    A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides. Side Zip Closure Cushioned Insole Leather Upper And Lining/Rubber Sole more

    $50.00

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    Free People Shoes | Free People James Chelsea Chunky Lug Sole Boot 11 | Color: Tan | Size: 11

    Free People Shoes | Free People James Chelsea Chunky Lug Sole Boot 11 | Color: Tan | Size: 11

    This Cool And Fashion Forward Bootie Is From Free People. A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides. Features: Lug Sole Style, Elastic Panels On Both... more

    $125.00

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    Tory Burch Shoes | Chelsea Boots | Color: Brown/Tan | Size: Various

    Tory Burch Shoes | Chelsea Boots | Color: Brown/Tan | Size: Various

    The Quintessential Chelsea Boot Flat, Comfortable And Ultra-Versatile. The Sixties Silhouette Is Updated With A Ribbed Elastic Back Gore And Exaggerated Welt Set Against Smooth Leather. The Low Stacked Heel Looks Great With Cropped Pants And Longer... more

    $250.00

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    Madewell Shoes | Madewell Bradley Chelsea Lugsole Boot | Color: Black | Size: 8

    Madewell Shoes | Madewell Bradley Chelsea Lugsole Boot | Color: Black | Size: 8

    Super Comfy But Selling To Downsize My Shoe Collection. Never Worn Was Final Sale. Hit The Streets In This Classic Pull-On Chelsea Boot With Superchunky Lug Soles. The Wide Elastic Gore Not Only Looks Cool, But Also Makes On-And-Offs So Easy. And,... more

    $150.00

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    Free People Shoes | Free People James Chelsea Black Boot 9.5 | Color: Black | Size: 9.5

    Free People Shoes | Free People James Chelsea Black Boot 9.5 | Color: Black | Size: 9.5

    A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides And Cushioned Footbed. Style With Light-Wash Distressed Jeans, Graphic Tee And Your Favorite Plaid... more

    $115.00

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    Free People Shoes | Free People James Chelsea Boot | Color: Tan | Size: 9

    Free People Shoes | Free People James Chelsea Boot | Color: Tan | Size: 9

    Free People James Chelsea Boot. Size 39. Tan Leather With Clear Sole. Barely Worn- Like New. Runs Narrow. Hidden Elastic-Gore Insets At The Sides. Size 39 = 9 3.5" Heel Height more

    $90.00

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    Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boot Ng679 | Color: Brown/Purple | Size: Various

    Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boot Ng679 | Color: Brown/Purple | Size: Various

    Hit The Streets In This Classic Pull-On Chelsea Boot With Superchunky Lug Soles. The Wide Elastic Gore Not Only Looks Cool, But Also Makes It Easier To Take On And Off. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On... more

    $91.00

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    Free People Shoes | Free People James Chelsea Boots Us Size 9 | Color: Black/Cream | Size: Various

    Free People Shoes | Free People James Chelsea Boots Us Size 9 | Color: Black/Cream | Size: Various

    Free People James Chelsea Boot New Without Box A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides. Make A Statement In These Leather Chelsea Boots Featuring A... more

    $59.00

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    Tory Burch Shoes | Chelsea Boots | Color: Brown/Tan | Size: 8.5

    Tory Burch Shoes | Chelsea Boots | Color: Brown/Tan | Size: 8.5

    The Quintessential Chelsea Boot Flat, Comfortable And Ultra-Versatile. The Sixties Silhouette Is Updated With A Ribbed Elastic Back Gore And Exaggerated Welt Set Against Smooth Leather. The Low Stacked Heel Looks Great With Cropped Pants And Longer... more

    $250.00

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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 Benning Chelsea Boot | Color: Gold/Tan | Size: 6.5

    Madewell Shoes | Madewell The Benning Chelsea Boot | Color: Gold/Tan | Size: 6.5

    Preowned In Great Condition! Madewell 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. When You Select Your... more

    $82.00

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    Madewell Shoes | Madewell Harvest Moon Cream Chelsea Lugsole Heeled Ankle Boots Size 8 Nh199 | Color: Black/Cream | Size: 8

    Madewell Shoes | Madewell Harvest Moon Cream Chelsea Lugsole Heeled Ankle Boots Size 8 Nh199 | Color: Black/Cream | Size: 8

    In Excellent Preowned Condition Madewell Boots. Size 8. Platform Chelsea Boot. Pull-On Style With Elastic Gore Insets. Classic Round Toe Silhouette. Pull Tab In Back For Easy On And Off Access. Leather And Textile Upper. Leather And Textile Insole.... more

    $130.00

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    Free People Shoes | Free People James Chelsea Boot Lugged Sole Size 38 | Color: Black/Cream | Size: 38eu

    Free People Shoes | Free People James Chelsea Boot Lugged Sole Size 38 | Color: Black/Cream | Size: 38eu

    Condition: Excellent Pre Owned, Worn Less Than An Hour Once. No Damage Or Flaws. A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides. Reviews Recommend They Run... more

    $97.00

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    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot Sz 10 Nn020 | Color: Black | Size: 10

    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot Sz 10 Nn020 | Color: Black | Size: 10

    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

    $89.00

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    J. Crew Shoes | Madewell The Wyckoff Chelsea Lugsole Boot | Color: Black | Size: 8.5

    J. Crew Shoes | Madewell The Wyckoff Chelsea Lugsole Boot | Color: Black | Size: 8.5

    New But Little Strap Thing On Heel Of One Shoe Broke. See Photo. I’m Sure It Could Be Fixed 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... more

    $99.00

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    Free People Shoes | Free People Lola Lugged Sole Chelsea Boots - Nib | Color: Black | Size: Various

    Free People Shoes | Free People Lola Lugged Sole Chelsea Boots - Nib | Color: Black | Size: Various

    These Handcrafted Pull-On Chelsea Boots Feature Italian Polished Leather With A Lug Sole For An Edgy Update On The Classic Chelsea Silhouette. Features: * Pull-On Style With Elastic Gore Insets * 1 3/4" Heel * 4 1/2" Shaft * Cushioned Footbed * Leather... more

    $248.00

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    Free People Shoes | Free People James Chelsea Boot, White Leather | Color: Black/White | Size: Various

    Free People Shoes | Free People James Chelsea Boot, White Leather | Color: Black/White | Size: Various

    Free People James Chelsea Boot In White Leather - New In Box! A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides. Side Zip Closure Cushioned Insole Leather Upper... more

    $125.00

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    Free People Shoes | Free People James Chelsea Boot - Size 10 | Color: Cream | Size: 10

    Free People Shoes | Free People James Chelsea Boot - Size 10 | Color: Cream | Size: 10

    Color: White - More Of An Off White/Cream Color A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides. Side Zip Closure Cushioned Insole Leather Upper And... more

    $45.00

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    Columbia Shoes | Columbia Fairbanks Rover Men’s Chelsea Waterproof Boots Size 10 Cordovan Sand | Color: Brown | Size: 10

    Columbia Shoes | Columbia Fairbanks Rover Men’s Chelsea Waterproof Boots Size 10 Cordovan Sand | Color: Brown | Size: 10

    Columbia Fairbanks Rover Men’s Chelsea Waterproof Boots Size 10 Cordovan Sand Shoe Features Waterproof Leather Upper With Gore Details To Create A Easy On, Easy Off Omni-Heat Reflective Lining 200g Insulation Techlite: Lightweight Midsole For Long... more

    $90.00

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    Free People Shoes | Free People James Chelsea Boot, Tan Leather | Color: Tan | Size: 38.5eu

    Free People Shoes | Free People James Chelsea Boot, Tan Leather | Color: Tan | Size: 38.5eu

    Free People James Chelsea Boot In Tan Leather - New In Box! A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides. Side Zip Closure Cushioned Insole Leather Upper And... more

    $125.00

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    Free People Shoes | Free People Atlas Chelsea Boots | Color: Tan | Size: 11

    Free People Shoes | Free People Atlas Chelsea Boots | Color: Tan | Size: 11

    Size 11 (41) Leather/Suede Rubber Sole Pull-On The Chelsea Boots Feature A Mixed Leather Upper With Scalloped Detailing And Stud Accents Pull-On With Elastic Gore Sides Leather And Textile Lining Lightly-Padded, Fixed Footbed Platform 1.5” more

    $95.00

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    More information about Men's Shoes

    Best prices on Double gore chelsea boot, Leather, 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.