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| Best Seller  | Women's Timberland Carnaby Cool Chelsea Boot - Brown - Ankle boots Elevate your collection in time for boots season with the Carnaby Cool Chelsea boot from Timberland. An OrthoLite® foam footbed brings a comofy level to this sharp pair. Nubuck leather... more | $109.99 $76.98 FREE shipping go to store |
 | Women's Dirty Laundry Vines Platform Chelsea Boot - Black - Ankle boots A lug sole amplifies the utilitarian appeal of this casual-cool Chelsea boot. more | $79.95 $48.95 FREE shipping go to store |
| Best Seller  | Women's Steve Madden Leopold Chelsea Boot - Brown - Ankle boots A lug sole updates a timeless Chelsea boot that will take you from the office to happy hour with casual-cool style. more | $99.95 $37.97 FREE shipping go to store |
 | Free People James Chelsea Boot 10 / 40 New Nib Tan Chunky Sole Boots A Cool Take On A Classic Style Boot Chunky Rubber Lug Sole With Soft Leather Upper Elastic Details With Side Zip Almond Toe Cushioned Insole Approximately 3.5" Heel Height Size 10... more | go to store |
 | Madewell Shoes | Madewell Boots Dani Chelsea Chunky Lug Sole Size 8.5 | Color: Black | Size: 8.5 Such A Cool And Comfortable Shoe At The Same Time, Very Sturdy And Great Quality. The Lug Soles On These Make These Good For Walking On Wet, Icy Sidewalks, The Leather Makes Them Cool, Trendy, And Versatile (I.E., They're Not Just A Rain Boot) Good Pre... more | go to store |
 | Make A Statement In These 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. These Are In Very Good Preowned... more | go to store |
 | London Rag Yadira Duotone Color Block Pointed Toe High Ankle Chelsea Boots - White Chelsea boots are essential for any womans shoe-drobe. Featuring a pull tab with gusset elastic for convenient wear. Give your look a real rock chick-vibe by pairing these boots with cool mom jeans and an oversized nonchalant tee. more | $75.99 $53.19 go to store |
 | Chelsea boots are essential for any womans shoe-drobe. Featuring a pull tab with gusset elastic for convenient wear. Give your look a real rock chick-vibe by pairing these boots with cool mom jeans and an oversized nonchalant tee. more | $75.99 $53.19 go to store |
 | Yosi Samra Melissa Chelsea Boot In Natural Snake Leather - Brown 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 $59.99 go to store |
 | Timberland Courmayeur Valley Chelsea - Womens 6 Brown Boot Medium *Complete your seasonal style with this cool Chelsea boot *Lightweight nubuck leather upper *Pull-on styling with twin gores *Two-part flex insole with removable OrthoLite® footbed *EVA midsole *Rubber lug outsole *1-1/2" heel height more | FREE shipping go to store |
 | Danner Bull Run Chelsea 6in Height Shoes - Women's Brown Wedge 11 Width M 15482-11-M Danner Bull Run Chelsea 6in Height Shoes - Women's Brown Wedge 11 Width M 15482-11-M. No matter how hot it may be outside or in the workshop these Women's Casual Shoes & Boots are unlined so they're lightweight and keep your feet cool but they're made... more | FREE shipping go to store |
 | Danner Bull Run Chelsea 6in Height Shoes - Women's Brown Wedge 7 Width M 15482-7-M Danner Bull Run Chelsea 6in Height Shoes - Women's Brown Wedge 7 Width M 15482-7-M. No matter how hot it may be outside or in the workshop these Women's Casual Shoes & Boots are unlined so they're lightweight and keep your feet cool but they're made of... more | FREE shipping go to store |
 | Danner Bull Run Chelsea 6in Height Shoes - Women's Brown Wedge 9 Width M 15482-9-M Danner Bull Run Chelsea 6in Height Shoes - Women's Brown Wedge 9 Width M 15482-9-M. No matter how hot it may be outside or in the workshop these Women's Casual Shoes & Boots are unlined so they're lightweight and keep your feet cool but they're made of... more | FREE shipping go to store |
 | Women's Eastland Ida Chelsea Boot - Blue - Ankle boots The Ida Chelsea boot from Eastland will complement any cool weather look. This leather pair features a memory foam footbed and lug sole for stable and comfortable steps. Nubuck leather upper.... more | FREE shipping go to store |
 | Women's MIA Jonna Lug Sole Chelsea Boot - Brown - Ankle boots A Chelsea boot combines with a combat boot to create this cool bootie with a raw-finish stacked heel and lug sole perfect for all your edgy moto looks. more | FREE shipping go to store |
 | Women's MIA Jonna Lug Sole Chelsea Boot - Black - Ankle boots A Chelsea boot combines with a combat boot to create this cool bootie with a raw-finish stacked heel and lug sole perfect for all your edgy moto looks. more | FREE shipping go to store |
 | Women's MIA Jonna Lug Sole Chelsea Boot - Brown - Ankle boots A Chelsea boot combines with a combat boot to create this cool bootie with a raw-finish stacked heel and lug sole perfect for all your edgy moto looks. more | $79.99 $59.99 FREE shipping go to store |
 | Women's Bogs Holly Chelsea Boot - Black - Ankle boots Give a cool update to your winter wardrobe with the Holly Chelsea boot from Bogs. Featuring a waterproof gold certified leather construction, this bootie has BLOOM eco-friendly, algae-based EVA... more | FREE shipping go to store |
 | The Platform Chelsea Sneaker Boot Women's Keds The Platform Chelsea Sneaker Boot - White - Ankle boots Look cool and classic with The Platform Chelsea sneaker boot from Keds. Complete with two silhouettes in one, this pair adds sporty vibes to a casual everyday style. Suede & synthetic... more | $84.99 $69.98 go to store |
 | Women's J.Crew Lug-Sole Chelsea Boots - Black - Ankle boots Step into fall with this cool take on the classic Chelsea boot, complete with a chunky lug sole. This leather was sourced from a tannery that's certified by the Leather Working Group (LWG), an... more | $278.00 $229.99 go to store |
 | Women's Sam Edelman Jayln Platform Chelsea Boot - White - Ankle boots Add eye-catching appeal to your cool weather looks with the Jayln Chelsea boot from Sam Edelman. This platform ankle bootie features flat studs embellishing the heel counter for a... more | $179.99 $84.98 FREE shipping go to store |
 | Women's BUENO Wanda Chelsea Boot - Brown - Ankle boots Your go-to style gets a cool definition with the Wanda Chelsea boot from Bueno. Made from leather, this pull-on boot assures easy on/off with its gore panels and back pull tab and is grounded by a... more | FREE shipping go to store |
 | Women's Andre Assous Peggy Chelsea Boot - Brown - Ankle boots Add trendy appeal to your cool weather look with the Peggy Chelsea boot from Andre Assous. This bootie features a snake print leather upper and chunky midsole for a touch of edge. Leather... more | $149.99 $49.98 go to store |
 | Women's BUENO Wanda Chelsea Boot - Black - Ankle boots Your go-to style gets a cool definition with the Wanda Chelsea boot from Bueno. Made from leather, this pull-on boot assures easy on/off with its gore panels and back pull tab and is grounded by a... more | FREE shipping go to store |
 | Women's Bogs Holly Chelsea Boot - Black - Ankle boots Give a cool update to your winter wardrobe with the Holly Chelsea boot from Bogs. Featuring a waterproof gold certified leather construction, this bootie has BLOOM eco-friendly, algae-based EVA... more | FREE shipping go to store |
 | Women's Andre Assous Peggy Chelsea Boot - Black - Ankle boots Add trendy appeal to your cool weather look with the Peggy Chelsea boot from Andre Assous. This bootie features a snake print leather upper and chunky midsole for a touch of edge. Leather... more | $149.99 $49.98 go to store |
 | Women's BUENO Wanda Chelsea Boot - Black - Ankle boots Your go-to style gets a cool definition with the Wanda Chelsea boot from Bueno. Made from leather, this pull-on boot assures easy on/off with its gore panels and back pull tab and is grounded by a... more | FREE shipping go to store |
 | Women's Pendleton Chelsea Rain Boot - Blue - Ankle boots Play it cool even during the wet climate donning the Chelsea rain boot by Pendleton. Rubber upper, comfy elastic panels, cushioned wool insole, molded latex midsole and slip-resistant rubber sole... more | FREE shipping go to store |
 | Women's Pendleton Chelsea Rain Boot - Black - Ankle boots Play it cool even during the wet climate donning the Chelsea rain boot by Pendleton. Rubber upper, comfy elastic panels, cushioned wool insole, molded latex midsole and slip-resistant rubber... more | FREE shipping go to store |
 | Women's Pendleton Chelsea Rain Boot - Red - Ankle boots Play it cool even during the wet climate donning the Chelsea rain boot by Pendleton. Rubber upper, comfy elastic panels, cushioned wool insole, molded latex midsole and slip-resistant rubber sole... more | FREE shipping go to store |
 | Women's AllSaints Hetty Chelsea Boot - Black - Ankle boots Bold logo lettering lends cool contrast to a clean-cut Chelsea boot that's sure to be a hit from season to season. 1 3/4" heel 5 1/4" shaft Pull-on style with elastic gore insets Rubber... more | FREE shipping go to store |
 | Make A Statement In These So Cool 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. **Please Note Boots Are Off White/ Sightly... more | go to store |
 | Nwob! Fast Shipping! 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... more | go to store |
 | Make A Statement In These So Cool 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. **Please Note Boots Are Off White/ Sightly... more | go to store |
 | Hit The Streets In This Classic Pull-On Chelsea Boot With Superchunky Lug Soles. The Wide Elastic Gore Not Only Looks Cool, But Also Makes It Easier To Take On And Off. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On... more | go to store |
 | 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 Insole... more | go to store |
 | Free People Shoes | Free People Scout Chelsea Boot Eu 37 Us 6.5 | Color: Brown | Size: Eu 37 Us 6.5 These Are Amazingly Comfortable Boots. Insoles Have Great Cushion And Leather Is So Soft. Nwob! Fast Shipping! So Cool, Street-Style Ready Chelsea Boots Featured In A Soft Leather Design With A Flat Sole And Bold Elastic Side Panels. Pull-On Style... more | go to store |
 | Free People Shoes | Free People James Chunky Heel Chelsea Boot White | Color: White | Size: Various 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. Brand New In Original Box. Msrp: $188... more | go to store |
 | Free People Shoes | Free People Atlas Puffer Chelsea Ankle Boots New | Color: Black | Size: 8.5 Nwob, No Flaws! Free People Atlas Chelsea Puffer Boot, Black These Adorable Boots Sold Out Instantly Everywhere! Multiple Sizes Avail Gleaming Studs And Scalloped Edges Contrast Against The Puffy Profile Of A So-Cool Chelsea Boot Crafted From Leather.... more | go to store |
 | 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 Insole... more | go to store |
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