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    Best Seller
    WIDE FIT Darcy Chelsea Boot - black

    WIDE FIT Darcy Chelsea Boot - black

    Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more

    $99.99 $69.99

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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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    Best Seller
    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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    Watson Chelsea Boot

    Watson Chelsea Boot

    Men's Thomas & Vine Watson Chelsea Boot - Brown - Casual boots Take the classic route to your suave styling with the Thomas & Vine Watson Chelsea boot. The wingtip toe with brogue detailing provides a timeless look, while the memory foam insole ensures... more

    $89.99

    FREE shipping

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    Watson Chelsea Boot

    Watson Chelsea Boot

    Men's Thomas & Vine Watson Chelsea Boot - Brown - Casual boots Take the classic route to your suave styling with the Thomas & Vine Watson Chelsea boot. The wingtip toe with brogue detailing provides a timeless look, while the memory foam insole ensures... more

    $89.99

    FREE shipping

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    WIDE FIT Darcy Chelsea Boot - black

    WIDE FIT Darcy Chelsea Boot - black

    Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more

    $99.99 $69.99

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    Washington Grand Laser Chelsea Boot

    Washington Grand Laser Chelsea Boot

    Men's Cole Haan Washington Grand Laser Chelsea Boot - Brown - Casual boots Look sharp in this polished leather Chelsea boot detailed with laser-cut perforations at the toe. Lightweight cushioning and a moisture-wicking lining mean all-day comfort and... more

    $450.00

    FREE shipping

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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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    WIDE FIT Vera Flat Tall Boot - brown

    WIDE FIT Vera Flat Tall Boot - brown

    A classic tall boot is essential in any well-rounded wardrobe. With stud detailing, a wide supportive fit, and strapped ankle accents, experience true comfort and style in the Vera Flat Tall Boot.Key Features Include:- Round toe boot- Side zip closure-... more

    $119.99 $83.99

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    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 11.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 11.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

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    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

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    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 10.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 10.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

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    Washington Grand Laser Chelsea Boot

    Washington Grand Laser Chelsea Boot

    Men's Cole Haan Washington Grand Laser Chelsea Boot - Brown - Casual boots Look sharp in this polished leather Chelsea boot detailed with laser-cut perforations at the toe. Lightweight cushioning and a moisture-wicking lining mean all-day comfort and... more

    $450.00

    FREE shipping

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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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    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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    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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    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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    Tory Burch Shoes | Excellent Condition Clean Tory Burch Expedition Chelsea Boot Size 8.5 | Color: Black | Size: 8.5

    Tory Burch Shoes | Excellent Condition Clean Tory Burch Expedition Chelsea Boot Size 8.5 | Color: Black | Size: 8.5

    Worn One Time! Clean!! Like New Can Even Tell They Were Worn. Runs True To Size, No Need To Size Up On This One. Super Comfy! A Rubber Toe Caps Off This Expedition-Seeking Leather Boot Crafted With Stretchy Side Goring And Balanced On A Block Heel For... more

    $300.00

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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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    Free People Shoes | Free People Nwot Nori Over The Knee Boot Size Boot Size 8 Never Worn Before. | Color: Black | Size: 8

    Free People Shoes | Free People Nwot Nori Over The Knee Boot Size Boot Size 8 Never Worn Before. | Color: Black | Size: 8

    Pull-On These So Cool And Effortlessly Edgy Boots Featured In An Over-The-Knee Style And Slim Silhouette With Stretchy Paneling, A Wavy Platform Sole, And Bold Square-Shaped Toe. Chunky Sole Cushioned Footbed Durable Rubber Outsole What’s Care Fp? This... more

    $250.00

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    Free People Shoes | Free People Outer Limits Over The Knee Boots | Color: Red | Size: 8

    Free People Shoes | Free People Outer Limits Over The Knee Boots | Color: Red | Size: 8

    Round Platform Toe. Wide Bumper. Stretch Fabric Construction. Fabric Upper, Rubber Soles. Partial Side Zip Closure. Approx. 27” Shaft Height. 15” Opening Circumference. 1.5” Platform. New In Box. Box Labels Color As ‘Red’, But Color Appears Burgundy. more

    $129.00

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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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    Free People Shoes | Free People Spectrum Berry Sock Boot Nwot 38 | Color: Purple | Size: 38eu

    Free People Shoes | Free People Spectrum Berry Sock Boot Nwot 38 | Color: Purple | Size: 38eu

    Statement Pull-On Ankle Boots Featured In A Stretchy Fabrication With A Rounded Toe And A Modern Mirrored Heel. Inside Zip Closure Padded Footbed Berry: Sleek Stretch Stain Made In Spain Heel: ~3.25 In Shaft: ~6.25 In Plum Purple more

    $75.00

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    WIDE FIT Vera Flat Tall Boot - brown

    WIDE FIT Vera Flat Tall Boot - brown

    A classic tall boot is essential in any well-rounded wardrobe. With stud detailing, a wide supportive fit, and strapped ankle accents, experience true comfort and style in the Vera Flat Tall Boot.Key Features Include:- Round toe boot- Side zip closure-... more

    $119.99 $83.99

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    Free People Shoes | Free People Satin Spectrum Sock Boot Rust Size 6 | Color: Orange | Size: 6

    Free People Shoes | Free People Satin Spectrum Sock Boot Rust Size 6 | Color: Orange | Size: 6

    Free People Satin Spectrum Sock Boot Rust Size 6 -Statement Pull-On Ankle Boots -Featured In A Stretchy Fabrication With A Rounded Toe -Modern Mirrored Heel. -Inside Zip Closure -Padded Footbed -Rust; Sleek Stretch Stain Made In Spain Heel: 3.25 In New... more

    $109.00

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    Tory Burch Shoes | -Tory Burch Leather Knee-High Black Boots | Color: Black | Size: 5.5

    Tory Burch Shoes | -Tory Burch Leather Knee-High Black Boots | Color: Black | Size: 5.5

    Tory Burch Leather Knee-High Boots Size 5.5 A Few Scuff Marks At The Front Of One Boot Stretchy Material At The Calf Plenty Of Life Left Heel Height: 3 1/4 In Platform Height: 1/4 In Shaft Height: 18 In Back Zipper Black Square Toes Block Heels more

    $50.00

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    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 8

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 8

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

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    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

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    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 13

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 13

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 12

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 12

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 11

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 11

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 11

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 11

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 10.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 10.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 9

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 9

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 9.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 9.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 13

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 13

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 10

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 10

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 12

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 12

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store

    More information about Men's Shoes

    Best prices on Rounded toe platform chelsea boots, 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.