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| Best Seller  | Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... ... more | go to store |
 | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged Made Of Water-Resistant Suede With A Rugged Lug Sole, These Pull-On Chelsea Boots Are Fully Lined In Real Shearling To Up The Cozy Factor. Basically: All-Weather Boots You'll... ... more | go to store |
| Best Seller  | Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Black - 10.5 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Red - 9.5 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Red - 12 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Men's Officine Creative Chelsea Ankle Boots - Brown - Casual boots Material:Leather/Leather/Leather. ... more | FREE shipping go to store |
 | Men's Doucal's Leather Chelsea Ankle Boots - Black - Casual boots Material:Calf Leather/Rubber/Calf Leather. ... more | FREE shipping go to store |
 | 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 go to store |
 | Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box ... more | go to store |
 | Madewell ‘The Grayson’ Chelsea Boot Black Leather Pointed Toe Ankle Booties Size: 10 Color: Black & Brown Style: J8293 Condition: Preloved Condition (Normal Signs Of Wear; Small Flaws To Leather Noted; Creasing At Toe Noted; Please See/Zoom In To All... ... more | go to store |
 | Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots Wear To Toes- Scuffing. Rubbing. Minor Scratching At Heels. Gently Used. Good Condition. Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut... ... more | go to store |
 | Brand: Free People Style: James Chelsea Boots Heeled Ankle Booties Color: White Material: Leather With Rubber Gum Sole Size: Eu 40, Fits Like A 9 Has A Slightly Narrow Fit In My Opinion, Though I Do Better With Wider Fit Shoes Condition: New, No Box.... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Red - 11 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Red - 8 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Black - 8 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Red - 12 - Womens Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Red - 13 - Womens Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Red - 8.5 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. ... more | $713.31 $606.31 FREE shipping go to store |
 | Men's Moncler Larue Chelsea Ankle Boots - Blue - Casual boots Larue Chelsea ankle boots in leather. Round toe Elasticated side panels Rear pull tab Rear logo ring Embossed logo at midsole Debossed logo at heel cap. 100% Leather. ... more | FREE shipping go to store |
 | Henry Country Ankle Chelsea Boot Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. ... more | $713.31 $606.31 FREE shipping go to store |
 | Men's Thom Browne Mid Top Chelsea Ankle Boots - Black - Casual boots Mid-top chelsea ankle boots by thom browne made of grained leather with elastic side bands, tricolor grosgrain loop tab, leather interior and crepe rubber sole. Composition: leather.... ... more | $1,656.00 $426.00 go to store |
 | Men's Doucal's Suede Chelsea Ankle Boots - Brown - Casual boots Material:Calf Suede/Rubber/Calf Leather. This item may not be on sale in France, UK, Italy, Belgium and Switzerland. ... more | $399.00 $259.00 FREE shipping go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 2cm 100% Calf Leather, 100% Rubber. Made in Italy. ... more | $676.86 $575.33 FREE shipping go to store |
 | Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. ... more | $676.86 $575.33 FREE shipping go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 4cm, Height: 14cm, Sole: 2.5cm 100% Leather, 100% Rubber, 72% Polyester, 28% Elastane. Made in Italy. ... more | $645.62 $581.06 FREE shipping go to store |
 | Women's Ann Demeulemeester Black Drees Chelsea Boots - Ankle boots Ankle-high buffed calfskin boots in black. ... more | $1,475.00 $502.00 FREE shipping go to store |
 | Slight Scuffs But Have Never Been Worn. They Are Beautiful And So So Comfortable But Too Big For Me (No Need To Size Up Tts) My Loss Your Gain. Open To Offers ... more | go to store |
 | Used Read Description Size: 10/11 Measurements: Details: No Rips Or Stains Condition:Good Smoke Free Home Always Open To Offers ... more | go to store |
 | Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. ... more | go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Medium Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... ... more | go to store |
 | Women's Mackage Storm Chelsea Boots - Black - Ankle boots Handcrafted ankle-high water-resistant buffed leather Chelsea boots in black. ... more | FREE shipping go to store |
 | Women's Mackage Storm Chelsea Boots - Black - Ankle boots Ankle-high handcrafted water-resistant buffed leather Chelsea boots in black. ... more | FREE shipping go to store |
 | Black Gomme Gommellone Chelsea Boots Women's Marsèll Black Gomme Gommellone Chelsea Boots - Ankle boots Ankle-high buffed calfskin Chelsea boots in black. Elasticized gusset at sides · Leather pull-loop at heel collar · Buffed calfskin lining in tan · Foam rubber platform sole · Platform:... ... more | $680.00 $252.00 go to store |
 | Women's Guidi 76v Chelsea Boots - Black - Ankle boots Handcrafted ankle-high grained horse leather Chelsea boots in black. Distressing throughout. ... more | $1,340.00 $630.00 FREE shipping go to store |
 | Women's MM6 by Maison Martin Margiela Chunky Chelsea Boots - Black - Ankle boots Ankle-high grained calfskin chelsea boots in brown. Contrast stitching in white. ... more | $475.00 $166.00 go to store |
 | Men's Zegna Brown Blake Chelsea Boots - Casual boots Ankle-high suede Chelsea boots in brown. ... more | $1,185.00 $830.00 FREE shipping go to store |
 | Men's Moncler Black Acqua Chelsea Boots - Casual boots Ankle-high textured rubber Chelsea boots. ... more | FREE shipping go to store |
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