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    Best Seller
    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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    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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    Best Seller
    Michael Kors Shoes | Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel 9 | Color: Cream/Tan | Size: 9

    Michael Kors Shoes | Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel 9 | Color: Cream/Tan | Size: 9

    Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel Size 9 A Sharply Bootie Fashioned From Smooth ,Burnished Black Leather Dials Up The Chic Appeal Of Your Daily Style, While Logo-Etched Hardware Flashes At The Heel For A Signature... more

    $20.00

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    Holloway Chelsea Boot

    Holloway Chelsea Boot

    Men's Territory Holloway Chelsea Boot - Brown - Casual boots A unique take on a traditional profile, the Holloway Chelsea boot by Territory is sure to catch the onlooker's attention. Elastic stretch panels at the ankle offer a comfortable slip-on... more

    $79.99

    FREE shipping

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    Ventura Chelsea Boot

    Ventura Chelsea Boot

    Men's Thomas & Vine Ventura Chelsea Boot - Black - Casual boots Make a charismatic entry in the Thomas & Vine Ventura Chelsea boot. A plush suede shaft gives a different dimension to the ankle boot, crafted with a genuine leather upper. An Extralight... more

    $99.99

    FREE shipping

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    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

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    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

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    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

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    Madewell Shoes | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

    Madewell Shoes | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

    Madewell 9.5 Spencer Short Chelsea Boot Style C1375 Mink Taupe Tan Color Stacked Heel No Original Box Slight Marks In Leather (See Photos) Excellent Used Condition 1.75" Heel Almond Toe Luxe Quality Stretch On Both Sides Offers Welcome. No Trades. more

    $36.00

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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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    Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

    Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

    Great Used Condition. Distressed Croc Chelsea Ankle Boots By Anthropologie Brand Sixtyseven In Black. Chic, Edgy Aesthetic, A Versatile Capsule Wardrobe Piece For The Season That Can Be Dressed Up Or Worn Casually. Slip-On Ankle Boots With Textured... more

    $50.00

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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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    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

    $100.00

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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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    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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    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite Straight- Leg Jeans. Detail We Love: Stretchy Side Panels Make Them Easier To Take On And Off. Leather Upper And Lining.... more

    $50.00

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    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown Size 8 Nwt From Marshall’s Cognac Brown Caramel Embossed Leather Upper Croc Back Zipper Closure Approx 1.5” Heel Stretchy Top Half Mixed Media Ankle Length more

    $100.00

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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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    Gucci Shoes | Gorgeous Men's Gucci Boots | Color: Black | Size: 11

    Gucci Shoes | Gorgeous Men's Gucci Boots | Color: Black | Size: 11

    Description: - Gucci Leather Ankle Chelsea Boots - Smooth Black Leather - Comfort Stretch Panel - Pull On Loop - Square-Toes - 1" Heel - Lesther Insoles - Tan Soles With "Gucci" Script - Made In Italy Fit: Boots By Gucci Typically Fit True To Size.... more

    $260.00

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    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 10.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 10.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

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    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 10.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 10.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 8

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 8

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 11

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 11

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 11

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 13

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 13

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 8.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 8.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

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    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 12

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 12

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 10.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 10.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 9.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 9.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 12

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 12

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 9.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 9.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 13

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 13

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 8.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 8.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 13

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 13

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 9

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 9

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 9.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 9.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 8.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 8.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 9

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 9

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store

    More information about Men's Shoes

    Best prices on H m ankle boots chelsea, Leather, Stretchable 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.