- SAVE $43.36$26.63$69.99Alfani Men's Luka 2 Pull-On Chelsea Boots, Created for Macy's - BordeauxMacy'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
- $32.46and uptotes Women's Everywear Chelsea Waterproof Ankle BootsAmazon & 2 more
- SAVE $20.00$76.99$96.99Rag & Co Molina Women's Leather High Heel Chelsea Boots, Size: 10, WhiteKohl's
- SAVE $43.36$26.63$69.99Sun + Stone Men's Hawkes Pull-On Chelsea Boots, Created for Macy's - BrownMacy's
- SAVE $55.67$13.83$69.50Wild Pair Brooklan Chelsea Booties, Created for Macy's - Black with Bone SoleMacy's
- SALEDunross & Sons Mens Boots. Chelsea Boot. Jayden Dress Boots for Men. Comfortable Leather Boots.Amazonć»Sale
- SAVE $38.75$11.24$49.99Sonoma Goods For LifeĀ® Brantlee Women's Chelsea Boot, Size: 5.5, BlackKohl's
- SAVE $59.25$19.75$79.00Madden Girl Kween Chelsea Boots, 7MBelk
- $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 $180.03$99.97$280.00Hudson Tall Leather Chelsea BootBanana Republic
- SAVE $60.00$20.00$80.00True Craft Joyrider Chelsea Boots, 11MBelk
- $79.99and upbcbg Boxxa Block Heel Chelsea Boot in Sugar Almond at Nordstrom, Size 5Nordstrom & 1 more
- SALEMen's Chelsea Dress Boots High or Mid Top Slip On Ankle Boot for Men Business Genuine Leather Work Daily Casual ShoesAmazonć»Sale
- SAVE $39.60$59.40$99.00Jbu Women's Peacock Water-Resistant Chelsea Booties - BlackMacy's
- SAVE $111.07$73.93$185.00Calvin Klein Men's Fenwick Pull On Chelsea Boots - Medium BrownMacy's
- $65.00and upWomen's Chelsea Rain Boot - OliveMacy's & 1 more
- $65.00and upChooka Waterproof Chelsea Rain Boot in Taupe at Nordstrom, Size 6Nordstrom & 1 more
- $65.00Women's Chelsea Rain Boot - 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
- 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
- $30.00and upTotes Men's Cirrus Chelsea Rainboots - Black 12Target & 3 more
- $29.40and uptotes Men's Everywear Chelsea Waterproof Ankle BootAmazon & 3 more
- SAVE $56.25$18.75$75.00Ocean + Coast Menard Chelsea Boots, Grey, 11MBelk
- $29.99and upJournee Collection Tayshia Chelsea Bootie | Women's | Taupe | Size 6 | Boots | Bootie | ChelseaDSW Designer Shoe Warehouse & 2 more
- SAVE $54.07$35.93$90.00Madden Men Men's Maxxin Mid Height Chelsea Boot - Dark BrownMacy's
- $189.95and upSOREL Joan Now Chelsea (Black/Black) Women's BootsZappos & 3 more
- SAVE $109.45$89.55$199.00The Men's Store at Bloomingdale's Men's Chelsea Boots - 100% ExclusiveBloomingdale's
- SALEAthlefit Women's Chelsea Boots Fashion Lug Sole Chunky Heel Slip on Elastic Ankle BootiesAmazonć»Sale
- $199.00Boss Men's Colby Leather Chelsea Slip On Boot - BlackMacy's
- $189.95and upSOREL Joan Now Chelsea (Omega Taupe/Gum 2) Women's BootsZappos & 3 more
- SAVE $54.07$35.93$90.00Madden Men Men's Maxxin Mid Height Chelsea Boot - Light Taupe SuedeMacy's
- SAVE $40.00$39.99$79.99Nautica Men's Wuzer Chelsea Boots - BlackMacy's
- SAVE $96.07$63.93$160.00Steve Madden Men's Sully Chelsea Boots - TanMacy's
- SAVE $92.07$22.93$115.00Zodiac Women's Teresa Pull-On Chelsea Lug Sole Booties - BirchMacy's
- SAVE $143.27$35.73$179.00Aqua College Women's Raine Waterproof Chelsea Boots, Created for Macy's - Brown SuedMacy'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
- SAVE $26.01$58.99$85.00Cliffs by White Mountain Mastery Women's Chelsea Boots, Size: 6.5 Wide, Lt BeigeKohl's
- $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
- $84.99and upKeds Chelsea Platform HighTop Sneaker | Women's | Black | Size 6 | SneakersDSW Designer Shoe Warehouse & 2 more
- SAVE $69.01$29.99$99.00Women's Eco Bay Knit Chelsea Boots Frost Gray 9(B) L.L.BeanL.L.Bean
- $99.00Women's Rugged Wellie Chelsea Boots Black/Dark Gum 7(B), Rubber L.L.BeanL.L.Bean
- SALEBruno Marc Men's Suede Leather Chelsea Ankle BootsAmazonć»Sale
- $43.53and upTommy Hilfiger Men's Risten Double Gore Chelsea Boots - Medium BrownMacy's & 1 more
- SAVE $35.00$35.00$70.00Jbu Men's Water Resistant Marsh Chelsea Duck Shoes - Dark Brown, BeigeMacy's
- $99.00and upL.L.Bean Rugged Wellie Chelsea Boot (Kelp Green/Black) Women's ShoesZappos & 1 more
- $124.99and upVintage Foundry Co Evans Chelsea Boot | Men's | Tan | Size 8.5 | BootsDSW Designer Shoe Warehouse & 1 more
- $55.24and upVance Co. Landon Men's Chelsea Boots, Size: 7, GreyKohl's & 2 more