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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Hogan Chelsea Boot

Hogan Chelsea Boot

Men's Vance Co. Hogan Chelsea Boot - Black - Casual boots Slip into the Hogan Chelsea boot by Vance Co for an instantly polished and graceful look. This vegan synthetic boot features stretch gore details to enable easy on/off and a Tru Comfort Foam... more

$79.99

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Best Seller
Tyler Chelsea Boot

Tyler Chelsea Boot

Men's Frye Tyler Chelsea Boot - Brown - Formal boots Stretchy side panels and a back pull-tab mean easy entry into this classic Chelsea boot made from smooth and buttery leather. more

$258.00

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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

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Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 13 Brown Boot Medium

Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 13 Brown Boot Medium

*Work boot from Georgia Boot *Full-grain leather upper *3D knit stretch collar *Stretch gusset *Pull-on fit *DuraBlend midsole provides excellent rebound and comfort *Fiberglass shank *Heat/chemical/abrasion and slip-resisting Carbo-Tec outsole *1-1/2"... more

$154.95

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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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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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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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Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 14 Brown Boot Medium

Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 14 Brown Boot Medium

*Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

$159.95

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Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 9 Brown Boot Medium

Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 9 Brown Boot Medium

*Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

$159.95

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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

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Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 11

Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 11

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 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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Daily Double Chelsea Boot

Daily Double Chelsea Boot

Men's Eastland Daily Double Chelsea Boot - Brown - Casual boots Dual pull-tabs and stretchy gore insets lend easy wear to a rich leather Chelsea boot grounded by a cushioned footbed for lasting comfort. more

$125.00

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Oswald Chelsea Boot

Oswald Chelsea Boot

Men's Thomas & Vine Oswald Chelsea Boot - Black - Casual boots Look fascinating in the Thomas & Vine Oswald Chelsea boot. Suede accent at the heel beautifully contrasts the premium leather upper of this pull-on boot that's supported on an Extralight... more

$59.99

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Corbin Chelsea Boot

Corbin Chelsea Boot

Men's Thomas & Vine Corbin Chelsea Boot - Brown - Casual boots Give your attire a polished update with the Corbin Chelsea boot from Thomas & Vine. This high-top profile is made from leather and comes with side goring panels for a precise fit and... more

$89.99

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Oswald Chelsea Boot

Oswald Chelsea Boot

Men's Thomas & Vine Oswald Chelsea Boot - Brown - Casual boots Look fascinating in the Thomas & Vine Oswald Chelsea boot. Suede accent at the heel beautifully contrasts the premium leather upper of this pull-on boot that's supported on an Extralight... more

$59.99

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Steam Chelsea Boot

Steam Chelsea Boot

Men's AllSaints Steam Chelsea Boot - Black - Casual boots Stretchy goring and a rubber sole enhance the ease and comfort of a leather chelsea boot that adds a polished and refined look to any ensemble. Leather upper and lining/rubber and leather sole... more

$299.00 $224.25

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Farsley Chelsea Boot

Farsley Chelsea Boot

Men's Barbour Farsley Chelsea Boot - Brown - Casual boots Stretchy side panels mean easy entry into this dapper Chelsea boot equipped with dual pull-tabs and a breathable cotton-blend lining. more

$220.00

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Patina Chelsea Boot

Patina Chelsea Boot

Men's Mezlan Patina Chelsea Boot - Black - Casual boots A side zipper and stretch goring lend easy wear to a sophisticated Chelsea boot rendered in smooth leather for styling versatility. Leather and textile upper and lining/rubber and leather sole... more

$450.00

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Leather Chelsea Formal Boots

Leather Chelsea Formal Boots

Men's Dolce & Gabbana Leather Chelsea Formal Boots - Brown - Casual boots 100% authentic Dolce & Gabbana Mens Chelsea formal boots Brown leather exterior Leather outer sole Stretch bands on the sides for easy entry and exit Zipper closure Logo details... more

$1,455.53 $740.57

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Matrix Chelsea Boot

Matrix Chelsea Boot

Men's AllSaints Matrix Chelsea Boot - Black - Casual boots Premium leather and stretchy elastic goring make this versatile Chelsea boot an optimal choice throughout the year. Pull-on style with elastic gore insets Leather and textile upper/leather... more

$379.00

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Corbin Chelsea Boot

Corbin Chelsea Boot

Men's Thomas & Vine Corbin Chelsea Boot - Black - Casual boots Give your attire a polished update with the Corbin Chelsea boot from Thomas & Vine. This high-top profile is made from leather and comes with side goring panels for a precise fit and... more

$89.99

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Port Chalmers Chelsea Boot

Port Chalmers Chelsea Boot

Men's Rodd & Gunn Port Chalmers Chelsea Boot - Brown - Casual boots Stretchy side panels mean easy entry into this versatile and stylish Chelsea boot crafted from burnished European leather. Pull-on style with elastic gore insets Leather and textile... more

$238.00

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Hanford Chelsea Boot

Hanford Chelsea Boot

Men's Thomas & Vine Hanford Chelsea Boot - Brown - Casual boots Step out in style and comfort with the Hanford Chelsea boot from Thomas & Vince. Dual stretch gores make this pull-on boot flexible and comfortable to wear. A Tru Comfort insole ensures... more

$99.99

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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

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Port Chalmers Chelsea Boot

Port Chalmers Chelsea Boot

Men's Rodd & Gunn Port Chalmers Chelsea Boot - Brown - Casual boots Stretchy side panels mean easy entry into this versatile and stylish Chelsea boot crafted from burnished European leather. Pull-on style with elastic gore insets Leather and textile... more

$238.00

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Tigran Chelsea Boot

Tigran Chelsea Boot

Men's Stacy Adams Tigran Chelsea Boot - Brown - Casual boots When it comes to looking cool and fashionable, you definitely have to go with the Stacy Adams Tigran Chelsea boot. Made using suede, this slip-on boot is detailed with modern welt that... more

$59.99 $44.98

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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

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Yellowstone Chelsea Hiking Boot

Yellowstone Chelsea Hiking Boot

Men's Territory Yellowstone Chelsea Hiking Boot - Black - Casual boots When the hills beckon, just lace-up the Territory Yellowstone Chelsea hiking boot and get going with confidence. The water-resistant boot has dual elastic stretch panels that offer... more

$84.99

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Cameron Chelsea Boot

Cameron Chelsea Boot

Men's Vagabond Cameron Chelsea Boot - Brown - Casual boots Side stretch panels and a rear pull-tab offer easy wear on a nubuck leather Chelsea boot grounded by a durable lug sole. more

$220.00

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Cameron Chelsea Boot

Cameron Chelsea Boot

Men's Vagabond Cameron Chelsea Boot - Black - Casual boots Side stretch panels and a rear pull-tab offer easy wear on a nubuck leather Chelsea boot grounded by a durable lug sole. more

$220.00

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All Terrain Series Water Resistant Chelsea Boot

All Terrain Series Water Resistant Chelsea Boot

Men's Blundstone All Terrain Series Water Resistant Chelsea Boot - Brown - Casual boots Dual pull-tabs and stretch side goring mean easy entry into this versatile and hardy Chelsea boot crafted with weather-ready suede. XRD technology in the heel... more

$244.95

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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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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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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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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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