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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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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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Best Seller
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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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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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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Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

A Contemporary Spin On The Classic Chelsea Style, These Timeless Ankle-Covering Boots Feature A Chunky Sole For An Exaggerated Look. A Neutral Boot To Pop Any Outfit Fp Collection Color Chalk Artisan Crafted From Fine Leathers And Premium Materials, Fp... more

$25.00

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Coach Shoes | Coach Elijah Chelsea Boots | Color: Red | Size: 8

Coach Shoes | Coach Elijah Chelsea Boots | Color: Red | Size: 8

Coach Elijah Chelsea Boots In Good Used Condition. Has Creases From Normal Wear. Polished Calf Leather Gives This Tomboyish Boot A Rich Sheen, While The Saddle-Colored Stripe On The Sole Is A Nod To Heritage Coach(Tm) Craftsmanship. Fashion Meets... more

$95.00

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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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Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8 Brown Boot W

Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8 Brown Boot W

*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 6" DuraBlend Sport Waterproof Chelsea - Mens 8 Brown Boot W

Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 8 Brown Boot W

*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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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

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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

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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

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

$78.00

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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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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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Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boots Nn020 9 | Color: Black/White | Size: 9

Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boots Nn020 9 | Color: Black/White | Size: 9

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. 6" Shaft Height (Based... more

$134.00

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Madewell Shoes | Madewell Ainsley Chelsea Boot - Black Leather - 8 | Color: Black | Size: 8

Madewell Shoes | Madewell Ainsley Chelsea Boot - Black Leather - 8 | Color: Black | Size: 8

Madewell Ainsley Chelsea Boot - Black Leather Size 8 Great Preowned Condition Great Black Leather That Has Been Conditioned And Great Grip Soles For Great Traction. As Shown In Pictures And Video Crafted From Buttery Leather, This Updated Chelsea Boot... more

$77.00

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