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    Best Seller
    Stephen Slip-on Chelsea Boots

    Stephen Slip-on Chelsea Boots

    Men's Tricker's Stephen Slip-on Chelsea Boots - Black - Casual boots 100% Calf Leather, 100% Fabric, 1000% Rubber. Made in United Kingdom. more

    $752.57 $551.69

    FREE shipping

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    Slip-on Chelsea Boots

    Slip-on Chelsea Boots

    Men's Hogan Slip-on Chelsea Boots - Gray - Casual boots 100% Suede. Made in Italy. more

    $406.37 $195.06

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    Best Seller
    Chelsea Slip-on Boots

    Chelsea Slip-on Boots

    Men's Tricker's Chelsea Slip-on Boots - Brown - Casual boots 100% Leather. Made in United Kingdom. more

    $713.75 $548.16

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    Madewell Shoes | Madewell The Chelsea Rain Boot Slip On Ankle Boots Waterproof Outdoors Size 8 | Color: Black | Size: 8

    Madewell Shoes | Madewell The Chelsea Rain Boot Slip On Ankle Boots Waterproof Outdoors Size 8 | Color: Black | Size: 8

    Pre-Owned, Gently Used. Typical Signs Of Prior Use, No Flaws Noted. Posh Ambassador Ships Within One Day Of Purchase 20% Off Bundles Of Two Or More Items Please Review All Photos Prior To Purchase Recently Cleaned But Some Stubborn Dirt May Remain more

    $50.00

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    Free People Shoes | Free People Azalea Taupe Distressed Slip On Chelsea Style Shoe Boot - Sz 38 | Color: Brown | Size: 38eu

    Free People Shoes | Free People Azalea Taupe Distressed Slip On Chelsea Style Shoe Boot - Sz 38 | Color: Brown | Size: 38eu

    Free People Azalea Taupe Distressed Slip On Chelsea Style Shoe Boot - Sz 38 7.5 Us Unique Pair Of Slip On Ankle Boots With A Low Profile And Chelsea Boot Elastic Stying On Sides For Easy Access. Love The Intricate Design Or The Overlapping Panels.... more

    $145.00

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    J. Crew Shoes | J. Crew Size 9 Black Slip On Chelsea Rain Boots | Color: Black | Size: 9

    J. Crew Shoes | J. Crew Size 9 Black Slip On Chelsea Rain Boots | Color: Black | Size: 9

    Great Condition! Only Worn A Handful Of Times more

    $28.00

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    ® Biltmore Chelsea Boot - Brown - Ugg Boots

    ® Biltmore Chelsea Boot - Brown - Ugg Boots

    Men's Ugg ® Biltmore Chelsea Boot - Brown - Casual boots A casual performance style for urban environments, this versatile boot features weather-ready innovations like seam-sealed construction and a custom, hollow-core outsole with lightweight foam... more

    $150.00 $105.00

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    Neumel Suede Platform Chelsea Boots - Black - Ugg Boots

    Neumel Suede Platform Chelsea Boots - Black - Ugg Boots

    Women's Ugg Neumel Suede Platform Chelsea Boots - Black - Ankle boots An early 2000s icon that was a defining cornerstone of Y2K fashion, UGG's legacy is rooted in its irresistibly cosy sheepskin silhouettes. Modelled on a practical style from founder... more

    $171.00

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    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 11 Brown Slip On Medium

    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 11 Brown Slip On Medium

    *The Georgia Boot Eagle One waterproof chelsea work boot packs heavy-duty performance in a lightweight easy-to-slip-on boot *SPR full-grain leather upper *Nylon pull tabs *Georgia waterproof system *4" shaft height *Twin elastic gore panels for a great... more

    $164.95

    FREE shipping

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    Georgia Boot RevAMP Chelsea Soft Toe - Mens 12 Black Slip On W

    Georgia Boot RevAMP Chelsea Soft Toe - Mens 12 Black Slip On W

    *Waterproof full-grain SPR leather upper *Slip-on styling with twin gore for easier on and off *AMP Memory Foam insole *Double-ribbed steel shank *EVA midsole *Oil-resistant rubber rand *Oil- and slip-resistant polyurethane outsole *ASTM F2892... more

    $150.95

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    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 11.5 Brown Slip On Medium

    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 11.5 Brown Slip On Medium

    *The Georgia Boot Eagle One waterproof chelsea work boot packs heavy-duty performance in a lightweight easy-to-slip-on boot *SPR full-grain leather upper *Nylon pull tabs *Georgia waterproof system *4" shaft height *Twin elastic gore panels for a great... more

    $164.95

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    Fur Fleece Lined Suede Thick Bottom Thermal Snow Boots, Slip On Wear Resistance Heighten Chelsea Snow Shoes, Flat Round Toe Fall Aesthetic Vintage Snow Boots

    Fur Fleece Lined Suede Thick Bottom Thermal Snow Boots, Slip On Wear Resistance Heighten Chelsea Snow Shoes, Flat Round Toe Fall Aesthetic Vintage Snow Boots

    Faster shipping. Better service more

    $71.99 $19.79

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    Fur Fleece Lined Suede Thick Bottom Thermal Snow Boots, Slip On Wear Resistance Heighten Chelsea Snow Shoes, Flat Round Toe Fall Aesthetic Vintage Snow Boots

    Fur Fleece Lined Suede Thick Bottom Thermal Snow Boots, Slip On Wear Resistance Heighten Chelsea Snow Shoes, Flat Round Toe Fall Aesthetic Vintage Snow Boots

    Faster shipping. Better service more

    $71.99 $19.79

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    Fur Fleece Lined Suede Thick Bottom Thermal Snow Boots, Slip On Wear Resistance Heighten Chelsea Snow Shoes, Flat Round Toe Fall Aesthetic Vintage Snow Boots

    Fur Fleece Lined Suede Thick Bottom Thermal Snow Boots, Slip On Wear Resistance Heighten Chelsea Snow Shoes, Flat Round Toe Fall Aesthetic Vintage Snow Boots

    Faster shipping. Better service more

    $71.99 $19.79

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    Slip-on Chelsea Boots

    Slip-on Chelsea Boots

    Men's Dolce & Gabbana Slip-on Chelsea Boots - Black - Casual boots 100% Calf Leather, 55% Coton, 45% Goatskin Leather. Made in Italy. more

    $869.50

    FREE shipping

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    Goodward R Lw Slip-on Chelsea Boots

    Goodward R Lw Slip-on Chelsea Boots

    Men's Church's Goodward R Lw Slip-on Chelsea Boots - Black - Casual boots 100% Calf Leather, 100% Rubber. Made in Italy. more

    $1,021.14 $421.86

    FREE shipping

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    Slip-on Chelsea Boots

    Slip-on Chelsea Boots

    Men's Hogan Slip-on Chelsea Boots - Brown - Formal boots 100% Calf Leather. Made in Italy. more

    $479.31 $299.09

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    Madewell Shoes | Madewell Chelsea Slip On Rain Boot In Black Matte Size 10 | Color: Black | Size: 10

    Madewell Shoes | Madewell Chelsea Slip On Rain Boot In Black Matte Size 10 | Color: Black | Size: 10

    - Streamlined Rain Boots With A Pull-On Chelsea Shape And Rugged Lug Soles. - 5.5" Shaft Height - 1.25" Heel. - Rubber Upper. - Cotton Lining. - Rubber, Composition Leather Sole. - Worn Once more

    $55.00

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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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    Columbia Shoes | Columbia Manama Suede Slip On Waterproof Chelsea Boots 9.5 | Color: Black/Gray | Size: 9.5

    Columbia Shoes | Columbia Manama Suede Slip On Waterproof Chelsea Boots 9.5 | Color: Black/Gray | Size: 9.5

    Waterproof Chelsea Columbia Mazama Pull-On Suede Leather Boots Omni Grip Black Waterproof Chelsea Boot Size 9.5. Style Bl3203. These Boots Are In Great Shape And Would Be Great In Snow And Rain. Used In Great Condition. more

    $45.00

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    Madewell Shoes | Madewell Joni Slip On Chelsea Boot | Color: Black | Size: 7

    Madewell Shoes | Madewell Joni Slip On Chelsea Boot | Color: Black | Size: 7

    Great Condition. Beautiful Boot. more

    $45.00

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    Madewell Shoes | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Size 8.5 | Color: Tan | Size: 8.5

    Madewell Shoes | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Size 8.5 | Color: Tan | Size: 8.5

    Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Slip On Stacked Block Heel Chelsea Style Ankle Length Western Leather Upper And Lining Taupe Color Size: 8.5 Condition: Good, Has Some Scuffing more

    $50.00

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    Madewell Shoes | Madewell Marco Black Leather Chelsea Clog Boots | Color: Black | Size: 9.5

    Madewell Shoes | Madewell Marco Black Leather Chelsea Clog Boots | Color: Black | Size: 9.5

    Madewell Marco Black Leather Chelsea Clog Boots Beautiful Color And Stylish Part Clog, Part Chelsea, These Comfy Pull-On Boots Are Cut At Just The Right Height To Look Cool With Cropped Jeans, Culottes And Skirts. Smooth Leather Upper And Insole. Heel... more

    $99.00

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    J. Crew Shoes | J. Crew Suede Chelsea Clog Boot Faux-Fur Lining Bronzed Clay Color Size 6.5 | Color: Cream/Tan | Size: 6.5

    J. Crew Shoes | J. Crew Suede Chelsea Clog Boot Faux-Fur Lining Bronzed Clay Color Size 6.5 | Color: Cream/Tan | Size: 6.5

    Made In Vietnam Great Condition Except For A Minor Blemish On The Vamp See Last Listing Photo Upper Suede Leather Lining Sock Faux Fur Synthetic Outer Sole Gold Color Studded Midsole Heel Height 2” Style Number Bd336 Quality Construction And... more

    $68.00

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    Free People Shoes | Free People West Johanna Chelsea Clog Boot Black Leather Eu 40 New | Color: Black | Size: 10

    Free People Shoes | Free People West Johanna Chelsea Clog Boot Black Leather Eu 40 New | Color: Black | Size: 10

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

    $145.00

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    Kate Spade Shoes | Kate Spade New York Star Chelsea Rain Boots 10m Slip On Round Toe Black Flawed. | Color: Black/Gold | Size: 10

    Kate Spade Shoes | Kate Spade New York Star Chelsea Rain Boots 10m Slip On Round Toe Black Flawed. | Color: Black/Gold | Size: 10

    Kate Spade New York Star Chelsea Rain Boots 10m Slip On Round Toe Black Flawed. Few Scratches Shown In Pictures Please Refer To Them For More Details For More Details Please Refer To Pictures. Questions? Feel Free To Contact Me Send Your Offer And... more

    $65.00

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    Free People Shoes | Free People Vance Chelsea Clog Boots, Oatmeal - Nib | Color: Black/Cream | Size: Various

    Free People Shoes | Free People Vance Chelsea Clog Boots, Oatmeal - Nib | Color: Black/Cream | Size: Various

    These Edgy Chelsea Style Boots Feature A High Shine Polished Leather, Front And Back Pull Tabs For Easy On/Off And A Chunky Platform Heel. Features: * Leather Upper * Pull-On Style * Rounded Toe * Cushioned Footbed * Rubber Outsole With Wood Platform *... more

    $298.00

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    Madewell Shoes | Madewell Bryce Chelsea Ankle Boot Block Heel Suede Slip-On Brown Size 6.5 | Color: Brown/Tan | Size: 6.5

    Madewell Shoes | Madewell Bryce Chelsea Ankle Boot Block Heel Suede Slip-On Brown Size 6.5 | Color: Brown/Tan | Size: 6.5

    Madewell Bryce Chelsea Ankle Boot Block Heel Suede Slip-On Brown Size 6.5 Madewell Bryce Chelsea Ankle Boot Block Heel Suede Slip-On Brown Size 6.5 Slip On Suede Side Panel Detail Closed Toe Almond Toe In Good Pre-Owned Condition R1 more

    $45.00

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    J. Crew Shoes | J Crew Chelsea Slip On Boot Aq659 Size 9 | Color: Brown | Size: 9

    J. Crew Shoes | J Crew Chelsea Slip On Boot Aq659 Size 9 | Color: Brown | Size: 9

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

    $65.00

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    Madewell Shoes | Madewell Clog Chelsea Boots | Color: Black | Size: 7

    Madewell Shoes | Madewell Clog Chelsea Boots | Color: Black | Size: 7

    Based On '70s Swedish Clogs, This Retro Bootie Is Handmade Using Traditional Techniques And Set On An Ergonomic Sole Crafted On A Wooden Platform Details: Leather Lining Rubber Sole Good Used Condition, Some Scuffs To Leather And Wood more

    $80.00

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    Madewell Shoes | Madewell Chelsea Nico Black Leather Boots Pointed Toe Ankle Slip On | Color: Black | Size: 7.5

    Madewell Shoes | Madewell Chelsea Nico Black Leather Boots Pointed Toe Ankle Slip On | Color: Black | Size: 7.5

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

    $40.00

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    Carhartt Shoes | Carhartt Boots Mens 9d Brown Leather Slip On Chelsea Work Slip Oil Resistant | Color: Brown | Size: 9

    Carhartt Shoes | Carhartt Boots Mens 9d Brown Leather Slip On Chelsea Work Slip Oil Resistant | Color: Brown | Size: 9

    Carhartt Chelsea Ankle Work Brown Leather Slip/Oil Resistant Boots Men's Size 9d There Elastic Is Stretched Out, There Are Scratches And Scuff Wear, See Photos. They Are Gently Loved Shoes, With Lots Of Life Left! The Pair Of Shoes In The Photos Are... more

    $49.00

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    Georgia Boot RevAMP Chelsea Soft Toe - Mens 12 Black Slip On Medium

    Georgia Boot RevAMP Chelsea Soft Toe - Mens 12 Black Slip On Medium

    *Waterproof full-grain SPR leather upper *Slip-on styling with twin gore for easier on and off *AMP Memory Foam insole *Double-ribbed steel shank *EVA midsole *Oil-resistant rubber rand *Oil- and slip-resistant polyurethane outsole *ASTM F2892... more

    $150.95

    FREE shipping

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    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 9.5 Brown Slip On Medium

    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 9.5 Brown Slip On Medium

    *The Georgia Boot Eagle One waterproof chelsea work boot packs heavy-duty performance in a lightweight easy-to-slip-on boot *SPR full-grain leather upper *Nylon pull tabs *Georgia waterproof system *4" shaft height *Twin elastic gore panels for a great... more

    $164.95

    FREE shipping

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    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 10.5 Brown Slip On Medium

    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 10.5 Brown Slip On Medium

    *The Georgia Boot Eagle One waterproof chelsea work boot packs heavy-duty performance in a lightweight easy-to-slip-on boot *SPR full-grain leather upper *Nylon pull tabs *Georgia waterproof system *4" shaft height *Twin elastic gore panels for a great... more

    $164.95

    FREE shipping

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    Georgia Boot RevAMP Chelsea Soft Toe - Mens 9 Black Slip On W

    Georgia Boot RevAMP Chelsea Soft Toe - Mens 9 Black Slip On W

    *Waterproof full-grain SPR leather upper *Slip-on styling with twin gore for easier on and off *AMP Memory Foam insole *Double-ribbed steel shank *EVA midsole *Oil-resistant rubber rand *Oil- and slip-resistant polyurethane outsole *ASTM F2892... more

    $150.95

    FREE shipping

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    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 8.5 Brown Slip On Medium

    Georgia Boot Eagle One Chelsea Soft Toe WP - Mens 8.5 Brown Slip On Medium

    *The Georgia Boot Eagle One waterproof chelsea work boot packs heavy-duty performance in a lightweight easy-to-slip-on boot *SPR full-grain leather upper *Nylon pull tabs *Georgia waterproof system *4" shaft height *Twin elastic gore panels for a great... more

    $164.95

    FREE shipping

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    Georgia Boot RevAMP Chelsea Soft Toe - Mens 10 Black Slip On Medium

    Georgia Boot RevAMP Chelsea Soft Toe - Mens 10 Black Slip On Medium

    *Waterproof full-grain SPR leather upper *Slip-on styling with twin gore for easier on and off *AMP Memory Foam insole *Double-ribbed steel shank *EVA midsole *Oil-resistant rubber rand *Oil- and slip-resistant polyurethane outsole *ASTM F2892... more

    $150.95

    FREE shipping

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    Georgia Boot RevAMP Chelsea Soft Toe - Mens 8.5 Black Slip On Medium

    Georgia Boot RevAMP Chelsea Soft Toe - Mens 8.5 Black Slip On Medium

    *Waterproof full-grain SPR leather upper *Slip-on styling with twin gore for easier on and off *AMP Memory Foam insole *Double-ribbed steel shank *EVA midsole *Oil-resistant rubber rand *Oil- and slip-resistant polyurethane outsole *ASTM F2892... more

    $150.95

    FREE shipping

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    Georgia Boot RevAMP Chelsea Soft Toe - Mens 9.5 Black Slip On W

    Georgia Boot RevAMP Chelsea Soft Toe - Mens 9.5 Black Slip On W

    *Waterproof full-grain SPR leather upper *Slip-on styling with twin gore for easier on and off *AMP Memory Foam insole *Double-ribbed steel shank *EVA midsole *Oil-resistant rubber rand *Oil- and slip-resistant polyurethane outsole *ASTM F2892... more

    $150.95

    FREE shipping

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    More information about Men's Shoes

    Best prices on Ryleigh chelsea boot, Boots, Weekender 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.