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| Best Seller  | Free People Women's Leather James Chelsea Boots - White Say hello to the perfect, most versatile boot. The ankle height makes this style easily transition from day to night. Wear them with your favorite skinny jeans and tee for a more laid back look, or pair them with your favorite mini dress and jacket for... more | $211.00 $126.00 go to store |
 | rag & bone Sloane Suede & Leather Chelsea Boots - White Say hello to the perfect, most versatile boot. The ankle height makes this style easily transition from day to night. Wear them with your favorite skinny jeans and tee for a more laid back look, or pair them with your favorite mini dress and jacket for... more | go to store |
| Best Seller  | Yosi Samra Melissa Chelsea Boot In White Leather - White Comfortable ankle boots with a little lift are the ultimate cool-girl shoes for fall. The Melissa Chelsea Boot has a stacked blocked heel, almond toe and comfortable memory foam footbed – perfect for both the office or a night out. The dual elastic... more | $198.00 $49.99 go to store |
 | Yosi Samra Melissa Chelsea Boot In White Leather - White Comfortable ankle boots with a little lift are the ultimate cool-girl shoes for fall. The Melissa Chelsea Boot has a stacked blocked heel, almond toe and comfortable memory foam footbed – perfect for both the office or a night out. The dual elastic... more | $198.00 $49.99 go to store |
 | rag & bone Sloane Suede & Leather Chelsea Boots - White Say hello to the perfect, most versatile boot. The ankle height makes this style easily transition from day to night. Wear them with your favorite skinny jeans and tee for a more laid back look, or pair them with your favorite mini dress and jacket for... more | $690.00 $368.00 go to store |
 | Regatta Womens/Ladies Harriett Ankle Boots - Navy/White Sand - Blue - 5 Pull-on chelsea boots in high-shine pvc (probably the most elegant wellington boot we have ever made). Waterproof uppers with a slimline sole and a small square heel. Comfortable eva footbed. Elastic at the side and a tab on the ankle makes for easy... more | $50.99 $22.95 go to store |
 | Regatta Womens/Ladies Harriett Ankle Boots - Navy/White Sand - Blue - 8 Pull-on chelsea boots in high-shine pvc (probably the most elegant wellington boot we have ever made). Waterproof uppers with a slimline sole and a small square heel. Comfortable eva footbed. Elastic at the side and a tab on the ankle makes for easy... more | $50.99 $22.95 go to store |
 | Regatta Womens/Ladies Harriett Ankle Boots - Navy/White Sand - Blue - 8.5 Pull-on chelsea boots in high-shine pvc (probably the most elegant wellington boot we have ever made). Waterproof uppers with a slimline sole and a small square heel. Comfortable eva footbed. Elastic at the side and a tab on the ankle makes for easy... more | $50.99 $22.95 go to store |
 | Regatta Womens/Ladies Harriett Ankle Boots - Navy/White Sand - Blue - 10 Pull-on chelsea boots in high-shine pvc (probably the most elegant wellington boot we have ever made). Waterproof uppers with a slimline sole and a small square heel. Comfortable eva footbed. Elastic at the side and a tab on the ankle makes for easy... more | $50.99 $22.95 go to store |
 | Regatta Womens/Ladies Harriett Ankle Boots - Navy/White Sand - Blue - 7 Pull-on chelsea boots in high-shine pvc (probably the most elegant wellington boot we have ever made). Waterproof uppers with a slimline sole and a small square heel. Comfortable eva footbed. Elastic at the side and a tab on the ankle makes for easy... more | $50.99 $22.95 go to store |
 | Regatta Womens/Ladies Harriett Ankle Boots - Navy/White Sand - Blue - 9 Pull-on chelsea boots in high-shine pvc (probably the most elegant wellington boot we have ever made). Waterproof uppers with a slimline sole and a small square heel. Comfortable eva footbed. Elastic at the side and a tab on the ankle makes for easy... more | $50.99 $22.95 go to store |
 | Regatta Womens/Ladies Harriett Ankle Boots - Navy/White Sand - Blue - 6 Pull-on chelsea boots in high-shine pvc (probably the most elegant wellington boot we have ever made). Waterproof uppers with a slimline sole and a small square heel. Comfortable eva footbed. Elastic at the side and a tab on the ankle makes for easy... more | $50.99 $22.95 go to store |
 | Recycled Buckle Chelsea Moto Booties Women's Ganni Recycled Buckle Chelsea Moto Booties - White - Ankle boots Ganni Chelsea ankle booties in shiny recycled polyester (fabric worked as leather) with buckle accent 2.00 in / 50 mm block heel Pointed toe Gored sides Pullon style Made in Portugal more | FREE shipping go to store |
 | Women's J.W. Anderson Heeled Boots - White - Ankle boots Frontal closure with zip. Detail with adjustable strap. Leather sole. Made in Italy. Leather. External : Leather. Made in Italy. Plain. New with tags. more | $759.00 $493.35 go to store |
 | J. Crew Shoes | J. Crew Black Suede Booties | Color: Black/White | Size: 6 J. Crew. Black Suede Leather With White Sole. Chelsea Boots. more | go to store |
 | Women's Toga Embellished Boots - Black - Ankle boots Ankle-high grained leather Chelsea boots in white. Graphic hardware throughout. more | $695.00 $209.00 go to store |
 | Women's Dolce Vita Stormy Rain Boot - White - Ankle boots Splash around in trendy appeal with the Stormy rain boot from Dolce Vita. This Chelsea bootie features a classic design with a waterproof construction to keep you dry without sacrificing style.... more | FREE shipping go to store |
 | J. Crew Shoes | J Crew Animal Print Booties | Color: Black/White | Size: 7.5 J Crew Leopard Tiger Animal Print Ankle Boots Size 7.5. Worn Once So Comfortable Just Trying To Downsize. These Can Be Worn All Year Even With Festival Or Boho Outfits, Classic All In Black Clothes, Or With A White Tee And Jeans. Very Versatile. Will... more | go to store |
 | J. Crew Shoes | J Crew Calf Hair Slip On Shoe/ Sneaker 8 | Color: Black/White | Size: 8 J. Crew Calf Hair Animal Print Slip-On Shoes Sneakers Elevate Your Look With These Fun Calf Hair Shoes By J. Crew Factory! Pair With Your Favorite Jeans, Leggings, And Skirts. - Ankle Boots & Booties Athletic Shoes Espadrilles Flats & Loafers Ballet... more | go to store |
 | J. Crew Shoes | J. Crew Size 10 Navy Striped Wedge Sandals | Color: Blue/White | Size: 10 J. Crew Navy/White Striped Wedge Sardinia E Spadrille Sandals Canvas Fabric Open Heel Rounded Toe Wrap Around Ties For Leg/Ankle Women's Size 10 In Gently Used Condition Tags Fashion Fall Booties Heels Boots Shoes Chic Designer Plaid Woven Sweater... more | go to store |
 | Steve Madden Amulet - Womens 8.5 White Boot Medium *Bring the bling to your look with this pull-on Chelsea boot *Synthetic upper with rhinestone-adorned strap detail. *Dual gores on the ankle high shaft for easy entry *Padded footbed *Lug sole *2" chunky heel more | $129.95 $51.97 FREE shipping go to store |
 | Steve Madden Amulet - Womens 9.5 White Boot Medium *Bring the bling to your look with this pull-on Chelsea boot *Synthetic upper with rhinestone-adorned strap detail. *Dual gores on the ankle high shaft for easy entry *Padded footbed *Lug sole *2" chunky heel more | $129.95 $51.97 FREE shipping go to store |
 | Women's White Mountain Caption Bootie - Black - Ankle boots If being comfortable and secure is your priority, go for the Cliffs by White Mountain Caption bootie. A side panel reflects the Chelsea inspiration behind the ankle bootie, designed with an... more | go to store |
 | Women's Coconuts Indie Bootie - White - Ankle boots Lend a cozy, stylish update to your outfits with the Indie bootie from Coconuts. This vegan, monochromatic Chelsea bootie with extended gore detail is made of synthetic upper with textured design for... more | FREE shipping go to store |
 | Women's White Mountain Caching Bootie - Brown - Ankle boots Simple yet elegant, the Caching bootie from White Mountain perfectly complements every look. This Chelsea bootie comes with an elastic gore detail, back pull tab and an inside zipper to offer... more | go to store |
 | Women's White Mountain Caching Bootie - Black - Ankle boots Simple yet elegant, the Caching bootie from White Mountain perfectly complements every look. This Chelsea bootie comes with an elastic gore detail, back pull tab and an inside zipper to offer... more | go to store |
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