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- SAVE $79.27$19.73$99.00Steve Madden Women's Mayslie Cap-Toe Chelsea Booties - Taupe SuedeMacy's
- SAVE $43.36$26.63$69.99Alfani Men's Luka 2 Pull-On Chelsea Boots, Created for Macy's - BlackMacy's
- SAVE $63.67$15.83$79.50Style & Co Tashh Pull-On Gore Chelsea Booties, Created for Macy's - Rust MicroMacy's
- SAVE $79.27$19.73$99.00Steve Madden Women's Leopold Chelsea Booties - Brown SuedeMacy's
- SAVE $68.07$16.93$85.00Baretraps Women's Daytona Chelsea Boots - Ice GrayMacy's
- SAVE $87.27$21.73$109.00Steve Madden Women's Leopold-f Pull-On Chelsea Booties - Tan SuedeMacy's
- $31.39and uptotes Women's Everywear Chelsea Waterproof Ankle BootsAmazon & 2 more
- SALELezzglt Rain Boots for Women and Men, Comfort Lightweight Cute Rubber Boots, Women's Mid Calf Waterproof Garden Boots, Platform Rubber Chelsea Ankle Adult Soft Rain Shoes and Outdoor Work ShoesAmazonć»Sale
- SAVE $20.00$76.99$96.99Rag & Co Molina Women's Leather High Heel Chelsea Boots, Size: 10, WhiteKohl's
- SAVE $95.27$23.73$119.00Tommy Hilfiger Women's Brae Mid Heel Pull On Chelsea Boots - Taupe- Faux SuedeMacy's
- SAVE $27.50$22.49$49.99Sonoma Goods For LifeĀ® Brantlee Women's Chelsea Boot, Size: 5.5, BrownKohl's
- SAVE $14.59$28.31$42.90Ladies Black Fashion Booties With Rhinestone Decoration Chunky Heel Chelsea BootsSHEIN
- SAVE $55.67$13.83$69.50Wild Pair Brooklan Chelsea Booties, Created for Macy's - Black with Bone SoleMacy's
- SAVE $43.36$26.63$69.99Sun + Stone Men's Hawkes Pull-On Chelsea Boots, Created for Macy's - BrownMacy's
- SAVE $59.25$19.75$79.00Madden Girl Kween Chelsea Boots, 9MBelk
- SALESUREWAY Men's Western Slip On Work/Casual Boots for Men,Pull-On Square-Toe Chelsea Boots,Extremely Comfortable Durable Proved,Superior Oil/Slip Resistant,Thicker Imported LeatherAmazonć»Sale
- $65.00and upChooka Waterproof Chelsea Rain Boot in Taupe at Nordstrom, Size 6Nordstrom & 1 more
- $65.00Women's Chelsea Rain Boot - BlackMacy's
- $65.00and upWomen's Chelsea Rain Boot - OliveMacy's & 1 more
- $27.73and upBCBGeneration Women's Boxxa Chelsea Bootie - BlackMacy's & 1 more
- SAVE $55.60$83.40$139.00BCBGeneration Women's Boxxa Chelsea Bootie - StoneMacy's
- SAVE $63.67$15.83$79.50Sun + Stone Veronikaa Pull-On Lug Chelsea Booties, Created for Macy's - Ecru CrocMacy's
- SAVE $12.60$22.00$34.60Womens Classic Black Chelsea Ankle Boots And Short Boots With Thick Platform VersatileSHEIN
- SALEAthlefit Women's Chelsea Boots Fashion Lug Sole Chunky Heel Slip on Elastic Ankle BootiesAmazonć»Sale
- SAVE $60.00$20.00$80.00True Craft Joyrider Chelsea Boots, 11MBelk
- SAVE $190.03$89.97$280.00Hudson Tall Leather Chelsea BootBanana Republic
- SAVE $46.00$33.99$79.99Nautica Men's Wuzer Chelsea Boots - BrownMacy's
- $79.99and upbcbg Boxxa Block Heel Chelsea Boot in Sugar Almond at Nordstrom, Size 5Nordstrom & 1 more
- SAVE $39.60$59.40$99.00Jbu Women's Peacock Water-Resistant Chelsea Booties - BlackMacy's
- SAVE $59.25$19.75$79.00Madden Girl Kween Chelsea Boots, 9.5MBelk
- SAVE $54.07$35.93$90.00Madden Men Men's Maxxin Mid Height Chelsea Boot - WineMacy's
- SALEVintage Foundry Co Womens Charmaine Handmade Burnished Rugged Classy Elegant Ankle Chelsea Boots w Adjustable Buckled Bands Side Zip Chunky Heels Victorian Combat Biker Engineer Western Goth Comic ConAmazonć»Sale
- $30.00and upTotes Men's Cirrus Chelsea Rainboots - Black 8Target & 3 more
- SAVE $15.24$20.46$35.70Men Minimalist Slip On Chelsea Boots Minimalist Beige Faux Suede BootsSHEIN
- SAVE $111.07$73.93$185.00Calvin Klein Men's Fenwick Pull On Chelsea Boots - Medium BrownMacy's
- $30.00and uptotes Men's Everywear Chelsea Waterproof Ankle BootAmazon & 3 more
- SAVE $109.45$89.55$199.00The Men's Store at Bloomingdale's Men's Chelsea Boots - 100% ExclusiveBloomingdale's
- SAVE $56.25$18.75$75.00Ocean + Coast Menard Chelsea Boots, Grey, 7MBelk
- SAVE $8.44$16.56$25.00Women Minimalist Slip On Chelsea Boots Preppy Outdoor BootsSHEIN
- SALEBruno Marc Men's Suede Leather Chelsea Ankle BootsAmazonć»Sale
- SAVE $15.20$28.50$43.70Minimalist Chunky Heeled Chelsea BootsSHEIN
- SAVE $7.49$21.31$28.80Womens Short Chelsea Rain Boots Fashionable Garden Waterproof Rubber Shoes Plastic WelliesSHEIN
- $189.95and upSOREL Joan Now Chelsea (Black/Black) Women's BootsZappos & 5 more
- SAVE $54.07$35.93$90.00Madden Men Men's Maxxin Mid Height Chelsea Boot - Dark BrownMacy's
- SAVE $55.67$13.83$69.50Wild Pair Grayce Chelsea Lug Booties, Created for Macy's - Black SmoothMacy's
- $189.95and upSOREL Joan Now Chelsea (Omega Taupe/Gum 2) Women's BootsZappos & 3 more
- SAVE $26.01$58.99$85.00Cliffs by White Mountain Mastery Women's Chelsea Boots, Size: 6.5, GreyKohl's
- SALEMen's Chelsea Dress Boots High or Mid Top Slip On Ankle Boot for Men Business Genuine Leather Work Daily Casual ShoesAmazonć»Sale
- $99.00Women's Rugged Wellie Chelsea Boots Black/Dark Gum 11(B), Rubber L.L.BeanL.L.Bean
- SAVE $8.00$19.00$27.00Nubuck PU Round Toe Chelsea BootsSHEIN
- SAVE $54.07$35.93$90.00Madden Men Men's Maxxin Mid Height Chelsea Boot - Light Taupe SuedeMacy's
- $99.00and upL.L.Bean Rugged Wellie Chelsea Boot (Kelp Green/Black) Women's ShoesZappos & 1 more
- $54.50Bar Iii Women's Animal-Print Mesh Midi Slipdress, Created for Macy's - Chelsea Zebra CMacy's
- SAVE $59.25$19.75$79.00Jellypop Shelley Chelsea Booties, 9MBelk
- $119.95and upPendleton Carico Lake Waterproof Chelsea Boot in Black at Nordstrom, Size 6Nordstrom & 1 more
- SALEJousen Men's Suede Chelsea BootsAmazonć»Sale
- $29.99and upJournee Collection Tayshia Chelsea Bootie | Women's | Tan | Size 6 | Boots | Bootie | ChelseaDSW Designer Shoe Warehouse & 2 more
- SAVE $92.07$22.93$115.00Zodiac Women's Teresa Pull-On Chelsea Lug Sole Booties - BlackMacy's
- SAVE $69.01$29.99$99.00Women's Eco Bay Knit Chelsea Boots Frost Gray 6(B) L.L.BeanL.L.Bean
- SAVE $143.27$35.73$179.00Aqua College Women's Raine Waterproof Chelsea Boots, Created for Macy's - Black LeatMacy's