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| Best Seller  | 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 | FREE shipping go to store |
 | 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 | go to store |
| Best Seller  | 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 | go to store |
 | 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 | go to store |
 | Madewell Shoes | Madewell The Benning Chelsea Boot Sz 7 Nn017 | Color: Black | Size: 7 New Without Box And A Defect There’s A Small Hole In The Elastic By The Seam In The Right Shoe See Pics Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite... more | go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 9 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 | FREE shipping go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | Men's Golden Goose Deluxe Brand ’S Chelsea Boots - Black - Casual boots A timeless silhouette: the Chelsea boot, featuring clean simple lines, is the perfect blend of style and comfort. This men’s model features a black leather upper and gold-colored... more | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | go to store |
 | Madewell Shoes | Madewell Ainsley Chelsea Boot In Metallic | Color: Gold | Size: 7 Like New Madwell Ainsley Chelsea Boot Gently Worn - Minor Scuffing Crafted From Metallic Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: We've Added An Extra Layer Of Padding To Make Them... more | go to store |
 | Low Chelsea Boots From Madewell. Heather Natural Color Snake-Embossed Leather Boot - Stretch On Sides With A Perfect Pointed Toe. Western Look. New Never Worn Outside. No Box Madewell Heather Natural Size 7 #Western #Southwestern #Work #Party #Snake more | go to store |
 | Madewell Shoes | Madewell 6.5 Ainsley Brown Leather Chelsea Boots | Color: Brown | Size: 6.5 Madewell 6.5 Ainsley Brown Leather Chelsea Boots. Used, Good Conditionsee Pictures, Plenty Of Life Left. Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl... more | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | J. Crew Shoes | J. Crew Pull-On Chelsea Suede Boots In Desert Sand | Color: Black/Tan | Size: 9 J. Crew Pull-On Chelsea Suede Boots In Desert Sand Feature A Leather Lining, Soft Suede With A Stretchy Side Panel, Just Pull 'Em On And Go! You'll Want To Reach For Our Easy Oh-So-Walkable Chelsea Boots Everyday. Item Does Not Include The Original Box. more | go to store |
 | Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Size 8.5 | Color: Black | Size: 8.5 Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Please Note: The Manufacturer Comments That These Boots Fit Narrow But Will Stretch With Wear Recommending Going Up A Size If You Have A... more | go to store |
 | Listing As Pre-Owned. Excellent Condition. Line On Inside Label To Prevent In Store Returns. Color: True Black Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite... more | go to store |
 | Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5 Madewell Leather Ankle Boots Gently Worn Elastic Stretch On Interior And Exterior Side Ankle Minor Scuffing On Left Shoe Shown In Photo more | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boots - Size: 7.5 | Color: Black | Size: 7.5 New Without Tags - No Call-Outs Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert 6" Shaft Height (Based On Size 7). 1 1/2" Heel Height. Leather... more | go to store |
 | 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 | go to store |
 | Madewell Shoes | Madewell Ainsley Chelsea Boot - Black 7.5 | Color: Black | Size: 7.5 Madewell Ainsley Chelsea Boot - Black Size 7.5 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.... more | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather | Color: Black | Size: Various Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: We've Added An Extra Layer Of Padding To Make Them Even Easier On The Feet. Logo On Sole Marked To Prevent Retail Store... more | go to store |
 | Madewell Shoes | Madewell The Benning Chelsea Boot Sz 6 Nn017 | Color: Black | Size: 6 Boots Are New Without Box, Display Item, So The Bottoms Are A Tad Dirty 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 Walking On... more | go to store |
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