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| Best Seller  | Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - 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 |
 | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 13 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
| Best Seller  | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 11 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
 | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 9 1/2 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
 | 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 |
 | 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 |
 | New With Box Free People James Tan Brown Leather Chunky James Chelsea Ankle Boots Inside Zippers, Chunky, Apx 3.5" Heel, 1" Platform Size 41 more | 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 | $694.65 $566.83 FREE shipping go to store |
 | Men's Tod's Chelsea Ankle Boots - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more | $587.78 $479.63 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 | $662.59 $572.48 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 |
 | Xtratuf 6 in Ankle Deck Boots - Men's Chocolate/Tan 12 22734-BRN-120 Xtratuf 6 in Ankle Deck Boots - Men's Chocolate/Tan 12 22734-BRN-120. Xtratuf crafted these Men's Rain Boots with a slip-resistant Chevron outsole that provides superior traction on even the slipperiest docks. Xtratuf Men's 6in Ankle-Height Deck Boots... more | FREE shipping go to store |
 | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 10 1/2 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
 | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 11 1/2 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
 | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 9 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
 | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 10 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
 | Men's Daily Double Chelsea Boots by Eastland® in Tan (Size 12 M) These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more | go to store |
 | Anthropologie Ankle Boots - Leather Upper And Lining - Pull-On Style - Stacked Heels - Taupe/Tan - Size 9 Gently Pre-Owned; Some Light Scrapes To Heels As Shown. more | go to store |
 | Madewell - The Grayson Brogue Chelsea Tan Suede Ankle Boot Size 8.5 Excellent Condition Small Scratches On Bottom Of Boot Size 8.5 Heel Height - 2.5 Western Boot Details Stacked Raw Leather Heels Pointy Toe Pull On Style 3” Shaft Height Suede Upper... more | go to store |
 | Free People James Chelsea Ankle Boot Tan 8 1/2 Brand New. Pet & Smoke-Free Home, Never Worn Sz 8 1/2 more | go to store |
 | Complement Your Classic Look With The New Keith Suede Chelsea Boot From Levi’s! These Handsome Chelsea Boots Feature Soft Suede Uppers With Dual Elastic Gore For Easy On And Off And Memory Foam Footbed For Lasting Comfort. more | go to store |
 | Madewell Shoes | Madewell Bryce Suede Leather Chelsea Ankle Boots Tan Size 7 | Color: Tan | Size: 7 Madewell Bryce Suede Leather Chelsea Ankle Boots Tan Size 7 Small Stacked Heel, Pull Tabs, Elasticized Panels, And An Almond Toe. Gently Used With Normal Wear. Small Spot On The Left Boot Toward The Opening On The Front. Most Wear Is On The Bottom... more | go to store |
 | Condition: Pre-Owned With Natural Cosmetic Wear Noted, See Photos. Size: 6 Color: Tan Material: Suede Leather Upper Measurements: Shaft Height: 4.5 In Heel Height: 1.75 In Made Of Textured Suede With A Comfy Elasticized Shaft And Grippy Lugsoles, This... more | go to store |
 | Anthropologie Shoes | Hoss Intropia - Tan Suede Ankle Chelsea Boots, 9 | Color: Brown/Tan | Size: 9 Hoss Intropia Tan Suede Ankle Boots With Back Zip Detail And Stacked Wooden Heel Pre-Owned - Fair Condition, Denim Dye Spot Transfers At The Edges On Top, Can Be Professionally Cleaned For Additional Cost, Added Vibram Sole, See Images, Ask Questions,... more | go to store |
 | Pre-Owned, Good Gently Used Condition Some Marks Madewell Bryce Suede Boots Heeled Ankle Boots Chelsea Camel Brown Chestnut Tan Size 7 Genuine Suede 2.5" Heel Offers Always Welcome Bundle Items To Save! Sorry No Trades Or Holds 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 |
 | Free People Arlo Santa Fe Croc Embossed Chelsea Ankle Boots Tan Size 37. Fit Close To A Larger Size 7.5 Has A Small Scuff Along Right Shoe On Front. Minimal, However Excellent Pre-Owned Condition Otherwise True To Size* Amp Up Your Style In Thie Arlo... more | go to store |
 | Soft Light Tan Leather Booties Buckle Strap And Adjustable Closure 3” Sturdy Heel Little Leather Bows On The Back Heel With The Kate Spade Logo Super Cute And Versatile Good Condition, Some Light Water Marks See All Photos For Condition I Ship Quickly... more | go to store |
 | Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. more | $732.05 $597.36 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 | $732.05 $597.36 FREE shipping go to store |
 | Burgundy Ankle Strap Chelsea Boots Women's Toga Burgundy Ankle Strap Chelsea Boots - Black - Ankle boots Ankle-high buffed calfskin Chelsea boots in burgundy. Signature hardware throughout. more | $605.00 $315.00 FREE shipping go to store |
 | Madewell Shoes | Bnib Madewell Sonia Snakeskin Chelsea Ankle Boots 6 | Color: Black/Tan | Size: 6 Python Snake Print Heather Natural Leather Chelsea Booties With Almond Toe And Stacked Wooden Heel, Comes With Box 1.75'' Heel 3'' Shaft Pull-On With Elastic Gore Insets Tapered, Stacked Heel Cushioned Footbed Leather Upper Leather Lining more | go to store |
 | Zara Shoes | Brown Suede Chelsea Ankle Boot | Color: Brown/Tan | Size: 8 Tall Ankle Boot Suede Chelsea Boot From Zara, Worn Once! more | go to store |
 | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Slip On Stacked Block Heel Chelsea Style Ankle Length Western Leather Upper And Lining Taupe Color Size: 8.5 Condition: Good, Has Some Scuffing more | go to store |
 | Free People Shoes | Free People Mountain Chelsea Ankle Boot- Nwot | Color: Brown/Tan | Size: 7 Free People X Daryl Robin Chelsea Boot. Intentionally Designed To Look.Distressed, These Are Like New. Love Them, But Slightly Too Tight On Me. Nwot. Offers Welcome! more | go to store |
 | Coach Chelsea Boots Ankle Bowery Booties Natural Haircalf Nwot - Without The Original Box more | go to store |
 | Coach Shoes | Coach Bowery Chelsea Ankle Boot In Camel | Color: Tan | Size: 5 The Bowery Chelsea Boot From Coach Takes A Classic Silhouette And Updates It With Modern Appeal. This Ankle Bootie Features A Sleek Almond Toe And Ombre Block Heel For An Eye-Catching Finish. Details: * Runs Large, Fits Like Size 6 * Suede Upper *... more | go to store |
 | Farylrobin Womens Grey Suede Leather Pointy Toe Chelsea Ankle Bootie Size: Us 6 With Slate Suede And Chelsea Styling, This Is The Perfect Fall Bootie. Condition: Excellent Pre-Owned Condition See Pictures For Details Worn Once Sole: Rubber Sole With... more | go to store |
 | J. Crew Shoes | J. Crew Leather Chelsea Ankle Boots Size 6 1/2 | Color: Brown/Tan | Size: 6.5 J. Crew Leather Chelsea Ankle Boots 6 1/2 Condition: Very Good Pre Owned Condition, Leather Is Still In Really Good Shape, Minor Wear On The Soles, Few Small Scuffs On Leather, As Showing In Pictures. Brown Leather With Black Elastic Panels On The... more | go to store |
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