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    Free People Shoes | Free People James Chelsea Chunky Y2k Gum Sole Boots White Black Fall Winter | Color: Cream/White | Size: Various

    Free People Shoes | Free People James Chelsea Chunky Y2k Gum Sole Boots White Black Fall Winter | Color: Cream/White | Size: Various

    Questions? Leave A Comment Below! more

    $59.00

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    Free People Shoes | Free People James Chelsea Chunky Y2k Gum Sole Boots White Black Fall Winter | Color: Cream/White | Size: 11

    Free People Shoes | Free People James Chelsea Chunky Y2k Gum Sole Boots White Black Fall Winter | Color: Cream/White | Size: 11

    Reposhing This Item I Purchased From @Treasuretrovvv. Loved Them And Wanted Them To Work Out For Me, But They Were A Bit Snug On My 11.5-12 Sized Foot. These Are A True 10-11. They Are Still Brand New In Box, Only Tried On Once. Questions? Leave A... more

    $100.00

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    Hiro Chelsea Boot

    Hiro Chelsea Boot

    Men's Taft Hiro Chelsea Boot - Brown - Casual boots Featuring streamlined construction, the TAFT Hiro Chelsea boot is just perfect for everything that falls between nine and dine! It has Italian boxcalf leather upper for a rich look and a pull-on style... more

    $294.99

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Brown - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

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    Yosi Samra Melissa Chelsea Boot In Black Leather - Black

    Yosi Samra Melissa Chelsea Boot In Black Leather - Black

    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 $99.99

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    Yosi Samra Melissa Chelsea Boot In Red Snake Leather - Red

    Yosi Samra Melissa Chelsea Boot In Red Snake Leather - Red

    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

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    Yosi Samra Melissa Chelsea Boot In Black Leather - Black

    Yosi Samra Melissa Chelsea Boot In Black Leather - Black

    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 $99.99

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    Wide Width Women's Lou Bootie by Bella Vita in Taupe (Size 8 W)

    Wide Width Women's Lou Bootie by Bella Vita in Taupe (Size 8 W)

    The Lou by Bella Vita is fashionable, comfortable, and the perfect companion for all your fall outfits. This contemporary Chelsea Boot offers stretch for fit paneling with an on-trend underslung chunky block heel. The lightweight and flexible outsole,... more

    $96.99

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    Wide Width Women's Lou Bootie by Bella Vita in Tan (Size 7 1/2 W)

    Wide Width Women's Lou Bootie by Bella Vita in Tan (Size 7 1/2 W)

    The Lou by Bella Vita is fashionable, comfortable, and the perfect companion for all your fall outfits. This contemporary Chelsea Boot offers stretch for fit paneling with an on-trend underslung chunky block heel. The lightweight and flexible outsole,... more

    $96.99

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    Wide Width Women's Lou Bootie by Bella Vita in Tan (Size 11 W)

    Wide Width Women's Lou Bootie by Bella Vita in Tan (Size 11 W)

    The Lou by Bella Vita is fashionable, comfortable, and the perfect companion for all your fall outfits. This contemporary Chelsea Boot offers stretch for fit paneling with an on-trend underslung chunky block heel. The lightweight and flexible outsole,... more

    $96.99

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    Women's Montana Bootie by French Connection in Cognac (Size 6 1/2 M)

    Women's Montana Bootie by French Connection in Cognac (Size 6 1/2 M)

    French Connection Women's Montana Ankle Booties Mid Heel Comfortable Work Fall Winter Pull On Fashion Shoes Heeled Chelsea Boots for Women with Elastic Side DetailManmade UpperManmade LiningManmade Outsole2.5" Heel height10.6" Boot leg... more

    $69.99

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    Comfortiva Seneca - Womens 6 Black Boot W

    Comfortiva Seneca - Womens 6 Black Boot W

    *Sophisticated but not buttoned up, this Chelsea boot is the fall essential you've been looking for *Distressed leather upper *Side zipper closure and elastic panel *Removable ALIGN molded footbed *Flexible and slip-resistant TPR outsole more

    $119.95

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    Comfortiva Seneca - Womens 6.5 Black Boot Medium

    Comfortiva Seneca - Womens 6.5 Black Boot Medium

    *Sophisticated but not buttoned up, this Chelsea boot is the fall essential you've been looking for *Distressed leather upper *Side zipper closure and elastic panel *Removable ALIGN molded footbed *Flexible and slip-resistant TPR outsole more

    $119.95

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    Born Cove - Womens 6 Brown Boot Medium

    Born Cove - Womens 6 Brown Boot Medium

    *This handcrafted Chelsea boot is your newest fall fashion must-have *Waterproof leather upper *Pull-on styling with twin gores *Leather and fabric lining *Removable microfiber-covered latex insole *Steel shank for added stability *Opanka handcrafted... more

    $159.95

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    Women's Lou Bootie by Bella Vita in Tan (Size 9 1/2 M)

    Women's Lou Bootie by Bella Vita in Tan (Size 9 1/2 M)

    The Lou by Bella Vita is fashionable, comfortable, and the perfect companion for all your fall outfits. This contemporary Chelsea Boot offers stretch for fit paneling with an on-trend underslung chunky block heel. The lightweight and flexible outsole,... more

    $89.99

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    Women's Mia Bootie by French Connection in Brown (Size 11 M)

    Women's Mia Bootie by French Connection in Brown (Size 11 M)

    French Connection Women's Mia Ankle Booties Comfortable Work Fall Winter Pull On Fashion Shoes Heeled Chelsea Boots for WomenManmade UpperManmade LiningManmade Outsole2" Heel height9.96" Boot leg circumferenceBootie available in sizes 6,6.5,... more

    $69.99

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    Women's Mia Bootie by French Connection in Brown (Size 7 M)

    Women's Mia Bootie by French Connection in Brown (Size 7 M)

    French Connection Women's Mia Ankle Booties Comfortable Work Fall Winter Pull On Fashion Shoes Heeled Chelsea Boots for WomenManmade UpperManmade LiningManmade Outsole2" Heel height9.96" Boot leg circumferenceBootie available in sizes 6,6.5,... more

    $69.99

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    J. Crew Shoes | J. Crew Frankie Ankle Boots 9.5 Chelsea Side Zip Leather Fall | Color: Black/Brown | Size: 9.5

    J. Crew Shoes | J. Crew Frankie Ankle Boots 9.5 Chelsea Side Zip Leather Fall | Color: Black/Brown | Size: 9.5

    Please Enlarge Photos To See Condition And Detail. J.Crew Ankle Boots Size 9.5 Color: Warm Sepia Brown. Leather Upper & Lining, Made In Brazil. Side Zip With Leather Pulls. Western Style Heel. Overall Very Nice Condition, Heels Show Some Wear On Outer... more

    $45.00

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Black - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Hilde Chelsea Boot

    Hilde Chelsea Boot

    Men's Crown Vintage Hilde Chelsea Boot - Brown - Casual boots The joys of fall include pumpkin spice lattes, bonfires, and experiencing all four seasons in one day. While the last one may be more of an annoyance, the Hilde Chelsea boots from Crown... more

    $59.99 $49.98

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Black - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    The Wyckoff Chelsea Lugsole Boot

    The Wyckoff Chelsea Lugsole Boot

    Women's Madewell The Wyckoff Chelsea Lugsole Boot - White - Ankle boots Ready for all your supercute fall 'fits, this leather Chelsea boot has a stretchy gore and a wear-all-day-everywhere chunky lugsole. And, cushiness alert: MWL Cloudlift Lite... more

    $198.00

    FREE shipping

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    The Wyckoff Chelsea Lugsole Boot

    The Wyckoff Chelsea Lugsole Boot

    Women's Madewell The Wyckoff Chelsea Lugsole Boot - Black - Ankle boots Ready for all your supercute fall 'fits, this leather Chelsea boot has a stretchy gore and a wear-all-day-everywhere chunky lugsole. And, cushiness alert: MWL Cloudlift Lite... more

    $198.00

    FREE shipping

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    Laney Chelsea Boot

    Laney Chelsea Boot

    Women's Born Laney Chelsea Boot - Brown - Ankle boots Impressively practical and chic, the Laney Chelsea boot from Born is a worthy addition to your fall footwear repertoire. This ankle bootie features Opanka hand crafted construction with burnished... more

    $99.99

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Red - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Black - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Hiro Chelsea Boot

    Hiro Chelsea Boot

    Men's Taft Hiro Chelsea Boot - Black - Casual boots Featuring streamlined construction, the TAFT Hiro Chelsea boot is just perfect for everything that falls between nine and dine! It has Italian boxcalf leather upper for a rich look and a pull-on style... more

    $294.99

    FREE shipping

    go to store
    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Black - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

    go to store
    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Black - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Brown - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Brown - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Laney Chelsea Boot

    Laney Chelsea Boot

    Women's Born Laney Chelsea Boot - Black - Ankle boots Move through the fall season in the Laney Chelsea boot from Born. A classic profile, this ankle bootie boasts a hand-crafted construction with soft hand-finished upper and a high-traction sole.... more

    $99.99

    FREE shipping

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    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Brown - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Iggie Chelsea Boot

    Iggie Chelsea Boot

    Women's Rocket Dog Iggie Chelsea Boot - Gray - Ankle boots Your fall look can be more elegant with the Iggie Chelsea boot from Rocket Dog. Coordinating elastic gores ensure a comfortable fit while wearing the lug bootie. A plush foam footbed offers the... more

    $79.99

    FREE shipping

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    The Wyckoff Chelsea Lugsole Boot

    The Wyckoff Chelsea Lugsole Boot

    Women's Madewell The Wyckoff Chelsea Lugsole Boot - Brown - Ankle boots Ready for all your supercute fall 'fits, this leather Chelsea boot has a stretchy gore and a wear-all-day-everywhere chunky lugsole. And, cushiness alert: MWL Cloudlift Lite... more

    $198.00

    FREE shipping

    go to store
    Florida Chelsea Boot

    Florida Chelsea Boot

    Women's BUENO Florida Chelsea Boot - Black - Ankle boots The Florida Chelsea boot from Bueno brings a bold look to your fall style. This ankle bootie is highlighted with ribbed goring, contrast stitching details and thick lug outsole. Leather upper.... more

    $169.99

    FREE shipping

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    Hilde Chelsea Boot

    Hilde Chelsea Boot

    Men's Crown Vintage Hilde Chelsea Boot - Brown - Casual boots The joys of fall include pumpkin spice lattes, bonfires, and experiencing all four seasons in one day. While the last one may be more of an annoyance, the Hilde Chelsea boots from Crown... more

    $59.99 $47.98

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    J. Crew Shoes | J. Crew Leather Chelsea Booties Ankle Boots Sz 7 | Color: Red/Tan | Size: 7

    J. Crew Shoes | J. Crew Leather Chelsea Booties Ankle Boots Sz 7 | Color: Red/Tan | Size: 7

    J. Crew Leather Booties In Deep Redwood Sz 7 In Awesome Condition, A Total Classic! more

    $70.00

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