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| Best Seller  | 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 |
 | Madewell Shoes | Madewell The Kat Suede Chelsea Boot | Color: Brown/Tan | Size: 6 Madewell The Kat Chelsea Boot In Brown Suede. Heeled Bootie With Classic Elastic Ankles For The Perfect Fit. Stacked Heel. Great With Wide Leg Or Bootcut Jeans For A Retro Vibe! Excellent Used Condition. Soles Are In Great Shape, Minor Wear To The... more | go to store |
| Best Seller  | Free People Shoes | Free People Onyx Chelsea Boots Size 7 | Color: Black | Size: 7 Luxe Leather With A Stacked Sole And Lived-In Look. Pull-On Style, Ankle Length, Chelsea Design, Leather Uppers, Rounded Square Toe, Rubber Outsole, Pull Tabs, Block Heel. Size 7 more | go to store |
 | Honey Brown Distressed Leather Pull-On Chelsea Style Ankle Boots With Burnished Toes, Leather Sole, And A 2.5" Stacked Block Heel, From Gee Wawa For Anthropologie. Good Condition With Minimal Wear On The Soles, Minor Wear To The Leather, And Color... more | go to store |
 | Madewell Shoes | New Madewell Sonia Chelsea Snakeskin Print Boot | Color: Gray/Tan | Size: Various Brand New Madewell Leather Sonia Chelsea Bootie. Perfect Ankle Boot With Snakeskin Print And Stacked Wood Like Heel. 1.75” Heel. Almond Shaped Toe With Tapered Heel. 3” Shaft. Fast Shipping. Bundle And Save. $188 Retail. Reviews Recommend To Size Up... more | go to store |
 | Madewell Shoes | Madewell Size 8 Snakeskin Ankle Boots | Color: Black/Brown | Size: 8 An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. - 1 3/4" Heel (Size 8.5) - 3" Shaft - Pull-On Style With Elastic Gore Insets - Cushioned Footbed - Leather Upper And... more | go to store |
 | Classically Cool Pointed Toe Leather Ankle Boots Features A Pull-On Style With V-Cutouts At Both Sides And A Stacked Heel. Features: * Buttery Soft Suede Leather * Pointed Toes * Leather Lining * Cushioned Leather Insole * Imported Measurements (Based... more | go to store |
 | Madewell Shoes | Madewell Lonny Leather Black Heeled Ankle Boots | Color: Black | Size: 9 In Excellent Condition Size 9 Heel Height 3.5 Inches Black Leather Ankle Boot. Stacked Heel, Strap Around Ankle Is Held In Place With Stylish Bronze Pin/Ball. Chelsea Boot Style Elastic Sides. more | go to store |
 | Madewell Shoes | ! Madewell $188 The Grayson Chelsea Boots J8294 | Color: Cream/Gray | Size: Various Madewell $188 The Grayson Chelsea Boots In Velvet Distressed Sand J8294 Per Madewell : Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut Them Low On The Ankle To Make Your Legs Look Even Longer. This Pair... more | go to store |
 | Madewell Shoes | Madewell Grayson Brogue Chelsea Boot | Color: Brown/White | Size: 7.5 Great Preowned Condition. Madewell Grayson Brogue Chelsea Boot In A White Suede. Taking Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforationsand Cut Them Low On The Ankle To Make Your Legs Look Even Longer, These Are... more | go to store |
 | Free People Shoes | Essential Chelsea Boots Nib | Color: Tan | Size: 9.5 Free People Essential Chelsea Boots Nib A Wardrobe Essential, These Spanish-Made Leather Chelsea Boots Feature A Faded Design With A Stacked Heel. Zipper Back Closure Cushioned Insole Elastic Side Accents Heel: 2.75 In Shaft: 6.42 In Ankle... more | go to store |
 | Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot | Color: Tan | Size: 8 Madewell The Grayson Brogue Chelsea Boot Pre-Owned Madewell Boots. One Very Minor Scratch On One Of The Top Of The Boots, Otherwise, Great Condition. Western Boot Details Stacked Raw Leather Heel Pointy Toe Brogue Perforationscut Them Low On The Ankle... more | go to store |
 | Madewell The Ramsey Chelsea Boot In Cream Leather. Style Ng671 With Classic Western Stitching And A Comfy Stacked Heel, This Leather Ankle Boot Is The Cutest (And Goes With Any And Everything). The Pull Tab And Covered Elastic Inserts Make Taking Them... more | go to store |
 | Madewell Shoes | Madewell Low Chelsea Boots ~ Snake Embossed | Color: Black/Tan | Size: 8.5 Madewell Low Chelsea Boots ~ Snake Embossed Leather Size 8.5 New In Original Box (No Lid) An Almond Toe & Tapered, Stacked Heel Bring A Contemporary Look To A Boot That Serves As A Versatile Work To Weekend Look. Casual Chic Ankle Booties Perfect For... more | go to store |
 | Madewell Shoes | Madewell Bryce Suede Chelsea Boots | Color: Black/Brown | Size: 9 Madewell Bryce Suede Chelsea Boot This Suede Chelsea Boot, With A Low-Key Western Vibe, Hit Right At The Ankle For A Modern And Streamlined Look. Sizing: True To Size. Almond Toe. Suede Construction. Side Goring. Back Pull-Tab. Stacked Heel. Approx. 4"... more | go to store |
 | Madewell Shoes | Madewell | Joni Block-Heel Chelsea Boot | Color: Red | Size: 8.5 In Soft Suede With A Low Stacked Heel, These Pull-On Chelsea Boots From Madewell Have A Slight Western Vibe. With A Narrow Toe And A Cool Little Dip In Front, This Easy Ankle Style Is Such A Perfect Wear-Every-Day-With-Everything Boot. Size 8.5. Orig... more | go to store |
 | Madewell Shoes | Madewell Grayson Brogue Chelsea Boots | Color: Brown | Size: 7 Gently Used. Excellent Pre-Loved Condition. Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforationsand Cut Them Low On The Ankle To Make Your Legs Look Even Longer. A Pull-On Style For In-Between... more | go to store |
 | Never Worn Before Everyday Ankle Boot With A Very Walkable Stacked Heel, In Soft Suede With Faux Shearling Lining. They Pair Well With Fall Florals, Straight-Leg Denim And Much More. Suede Upper. Faux Fur Lining. Synthetic Sole. Color: Melted Caramel... more | go to store |
 | Madewell $198 The Grayson Brogue Chelsea Boots Amber Brown J8292 Per Madewell Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforationsand Cut Them Low On The Ankle To Make Your Legs Look Even... more | go to store |
 | Madewell Shoes | Madewell Tan Leather The Carina Ankle Boot With Side Gusset | Color: Tan | Size: 10 With An Easy Rounded Toe And Comfy Stacked Mid-Height Heel, These Wear-Everywhere Leather Chelsea Boots Have Elastic Goring And A Pull-Tab That Makes On-And-Off A Breeze. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well,... more | go to store |
 | Madewell Shoes | Madewell The Grayson Brogue Chelsea Ankle Bootie Brown Sz 7 | Color: Tan | Size: 7 Madewell Tan Brown The Grayson Brogue Chelsea Boots J8292 Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforationsand Cut Them Low On The Ankle To Make Your Legs Look Even Longer. A Pull-On Style... more | go to store |
 | Madewell Shoes | Madewell Black Sonia Leather Chelsea Ankle Bootie | Color: Black | Size: 9 An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. 1 3/4" Heel 3" Shaft Pull-On Style With Elastic Gore Insets Cushioned Footbed Leather Upper And Lining/Synthetic Sole... more | go to store |
 | Free People Shoes | Nib Faryl Robin + Free People Mountain Peak Boot | Color: Blue/Tan | Size: 7 Faryl Robin + Free People Mountain Peak Chelsea Boot. Size 7. New. Includes Box. Classic Chelsea Style Ankle Boots Featured In A Washed And Distressed Leather: Contrast Side Goring Stacked Heel Strip Of Metal Grommets Down The Back Pull Tab At The... more | go to store |
 | Coach Shoes | Coach Black & White Embossed Faux Snake Leather Boots | Color: Black | Size: 11 Coach Ankle Boots Comes In A Black & White Textured Embossed Faux Snake Skin Featuring A Chelsea Style, Pointed Toe, Studded Details, And A Stacked Heel. Very Good Pre-Owned Condition. Marked: 11 B Measurements: Length: 11.5 Inches Width: 4 Inches... more | go to store |
 | Bristol Chelsea Boot - Brown - Kork-Ease Boots Women's Kork-Ease Bristol Chelsea Boot - Brown - Ankle boots Dual goring panels and a rear pull-tab lend classic elements to a rich leather Chelsea boot grounded by a cushioned footbed and stacked heel. more | FREE shipping go to store |
 | Irnie Block Heel Chelsea Boot - Brown - Dolce Vita Boots Women's Dolce Vita Irnie Block Heel Chelsea Boot - Brown - Ankle boots An angular chisel toe balances the chunky stacked heel of this updated Chelsea boot finished with covered elastic insets and a pull-tab for easy-on styling. more | $140.00 $84.00 FREE shipping go to store |
 | Sahara Block Heel Chelsea Boot - Black - Paul Green Boots Women's Paul Green Sahara Block Heel Chelsea Boot - Black - Ankle boots A treaded sole and stacked block bring a touch of edge to this round-toe Chelsea boot featuring flexible hidden gore insets and a side zip for easy on and off. 3 1/4" heel; 3/4"... more | $520.00 $360.00 FREE shipping go to store |
 | Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 1/2 D) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 6E) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 EE) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Black Leather (Size 9 1/2 D) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Black Leather (Size 11 1/2 D) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 D) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 1/2 D) Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more | go to store |
 | Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 9 W) These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more | $90.99 $69.99 go to store |
 | Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (Size 13 W) These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more | $90.99 $69.99 go to store |
 | Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 12 W) These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more | $90.99 $69.99 go to store |
 | Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 16 M) These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more | $119.99 $69.99 go to store |
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