Women's Sole Society 'Ines' Chelsea Boot
More Details Uptown chic meets downtown edge with this go-to Chelsea bootie shaped from distressed leather and set on a chunky woodgrain heel.
Men's Ted Baker London 'Camroon 4' Chelsea Boot
More Details Paisley-patterned elastic-gore side panels intensify the suave vintage style of a definitive Chelsea boot completed with a subtly textured heel panel. Pull-up style. Leather upper/leather and textile lining/leather and rubber sole. By Ted Baker London; imported. Available online only.
Men's Vince Camuto 'Bradbury' Chelsea Boot
Now: $179.90 20% off
More Details A handsome profile and classic welt construction define a glossy leather Chelsea boot outfitted with smart elastic gores and a combo leather-rubber sole.
Men's George Brown Bilt Fulton Chelsea Boot
More Details Refine your casual look with the classic style of an Italian-crafted Chelsea boot grounded by a flexible leather and rubber sole.
Men's Eastland 'Daily Double' Chelsea Boot
More Details Cast in a sleek profile, a smart, comfort-minded Chelsea boot is crafted in smooth leather with a shock-absorbing insole and a slip-resistant rubber sole.
Women's Ugg Bonham Chelsea Boot
More Details A classic Chelsea boot gets a rugged update from waxed, water-resistant leather and a lugged rubber sole. The UGGpure lining naturally wicks moisture and regulates temperature, while the PORON® footbed cushions your feet wherever your adventures take you.
Men's Geox 'Fiesole - Abx' Amphibiox Waterproof Chelsea Boot
Now: $107.90 53% off
More Details Stay polished and put together even in wet, rainy weather with the Amphibiox Fiesole Chelsea boot from Geox, designed to repel water from the upper and sole while offering superior breathability and thermal insulation. Weathered Italian leather and meticulous tonal topstitching make the style a go-to professional staple.
Men's Robert Wayne Oregon Chelsea Boot
More Details Stretchy panels at the sides emphasize the comfortable fit of a handsome Chelsea boot crafted from rich leather. Pull-on style with pull tab and elastic gore insets Lightly padded footbed Leather upper and lining/synthetic sole Made in Portugal Men's Shoes
Men's Monte Rosso Enrico Chelsea Boot
More Details Rich suede textures an Italian-made Chelsea boot fitted with twin elastic goring panels and a flexible rubber sole.
Men's Samuel Hubbard 24 Seven Chelsea Boot
More Details Full-grained cowhide leather is shaped into a handsome chukka book with a one-piece vamp for a clean, minimalist look. A breathable, triple-density PORON® memory-foam insole with an antimicrobial finish offers superior cushioning, while a Vibram® MorFlex sole adds lightweight and durable support. American Podiatric Medical Association (APMA) Seal of Acceptance Pull-on style; elastic goring on each side Removable insole ...
Women's Blundstone Footwear 'Original - 500 Series' Water Resistant Chelsea Boot
More Details A good-looking Chelsea boot made from hand-vintaged suede features XRD® impact-protection technology in the heel for excellent shock absorption, and a breathable, Poron-cushioned footbed that can be removed and washed when you want to freshen it up. Chunky mixed treads and a low, stable heel provide excellent traction on wet and icy surfaces, and the thick sole adds insulated protection against underfoot contact ...
Women's Napa Flex 'Sarina' Chelsea Boot
More Details A stacked heel gives a slight lift to a quintessential Chelsea boot that offers all-day comfort with arch-supporting cushioning and a lightweight, flexible sole.
Women's Loeffler Randall 'Carmen' Chelsea Boot
More Details Soft, supple leather defines a sleek almond-toe Chelsea boot accented with inset elastic goring for easy on and off. A contrasting leather sole and modest stacked heel provide a trend-right finish.
Women's Napa Flex Jet Chelsea Boot
More Details Pieced leather, a distressed finish and a stretchy goring panel make this boot feel and look like an old favorite the minute you put it on. An articulated lug sole adds flexibility and grip when you need it. 1 1/4" heel (size 39) 4" shaft Side zip closure Leather and textile upper/leather lining/synthetic sole Imported Women's Shoes Helpful info: Boot Fit Fundamentals (video) , How to Measure Boots
Women's Børn Madyson Chelsea Boot
More Details The classic Chelsea boot gets a rugged upgrade with a no-nonsense lugged sole and a stacked block heel.The brand's Opanka handcrafting technique, dual-density foam cushioning with arch support and a super-lightweight, durable sole with slip-resistant treads make it comfortable to wear all day long. 2 1/4" heel Pull-on style with side elastic-goring insets Tuckerboard with steel shank; Opanka handcrafted construction ...
Women's Dr. Martens Bianca Chelsea Boot
More Details A sturdy lugged sole and logo heel tab refresh a classic Chelsea boot with Dr. Martens' signature combat-punk attitude. 1 1/4" heel; 1/2" platform (size 5US) 5" shaft Pull-on style with elastic side panels Leather upper and lining/rubber sole Imported BP. Shoes Helpful info: Shoe Fit Fundamentals (video) , How to Measure Boots
Women's Kendall + Kylie 'Finley' Chelsea Boot
More Details A pointy toe and bold block heel add unmistakable modern allure to the classic silhouette of a burnished leather Chelsea boot. Fusing the two Jenner sisters' distinct styles into a unified collection, KENDALL + KYLIE plays up both Kendall's more refined femininity and Kylie's dynamic edge. 3" heel (size 8.5) 4 1/2" shaft Pull-on style with elastic-gore insets Leather and textile upper/synthetic lining and sole Imported ...
Women's Jeffrey Campbell Cloudy Chelsea Rain Boot
More Details A Chelsea rain boot cut from faux leather is lifted by a platform and lugged sole so you can take on wet weather in confident style.
Women's Blundstone Footwear 'Original Series' Water Resistant Chelsea Boot
More Details A good-looking Chelsea boot made from smooth leather features XRD® impact protection technology in the heel for excellent shock absorption, and a breathable, PORON®-cushioned footbed that can be removed and washed when you want to freshen it up. Chunky mixed treads and a low, stable heel provide excellent traction on wet and icy surfaces, and the thick sole adds insulated protection against underfoot contact temperatures.
Men's Blundstone Footwear Chelsea Boot
More Details A heat-resistant, oil-resistant sole grounds a rugged Chelsea boot crafted from durable leather.
Women's Fly London 'Salv' Chelsea Boot
More Details A lugged wedge sole underscores the old-school attitude of a tried-and-true Chelsea boot shaped from lightly weathered and distressed leather.
Men's Prada Chelsea Boot
More Details This classic Chelsea boot crafted in gorgeous cordovan spazzolato leather features demure goring panels on the shaft. A stacked platform and sole provide a hardy foundation and a steadfast sense of style.
Women's Klr Lee Chelsea Boot
More Details A studded strap and sturdy lugged sole infuse moto-chic style into a Chelsea-inspired boot cut from pebbled leather and set on a memory-foam footbed.
Women's Bos. & Co. Caila Waterproof Chelsea Boot
More Details A cozy wool lining helps to keep your toes toasty-warm in a waterproof Chelsea boot temperature-rated to -25 C / -13 F and grounded by a grippy lugged sole.
Men's Josef Seibel 'Oscar 29' Chelsea Boot
More Details Soft, mixed-finish leather panels support stretchy goring to create an ultra-comfortable boot outfitted with a plush insole and a grippy lug sole. Pull-on style Removable padded footbed Leather upper/textile lining/synthetic sole By Josef Seibel; imported Men's Shoes
Women's Blundstone Footwear Chelsea Boot
More Details Sturdy, water-resistant leather lends versatile appeal to an on-trend Chelsea boot styled with a squared-off toe and set on a heat-resistant sole. An anatomically designed, shock-absorbing PORON® XRD® footbed provides all-day comfort.
Women's Ecco 'Shape 25' Chelsea Boot
More Details This essential Chelsea boot is crafted from premium leather with tonal goring panels that look smart day or night. A generously cushioned footbed and a grippy, lightweight sole keep it comfortable everywhere you wear it.
Men's Ariat 'Spot Hog' Chelsea Boot
More Details A rugged lug sole grounds a rugged-style Chelsea boot shaped from tough leather and fitted with 4LR Advanced Cushioning for all-day comfort.
Women's Hispanitas 'Lourdes' Chelsea Boot
More Details Bold snake embossing adds a contemporary update to the back of a quintessential Chelsea boot cut from smooth leather and set on a lugged sole.
Women's The Flexx Slimmer Chelsea Wedge Boot
More Details A grippy textured sole and wedge heel put a modern spin on a classic Chelsea boot fitted with a cushioned footbed for all-day comfort.
Men's Bed Stu 'Royce' Chelsea Boot
More Details A hand-distressed finish underscores the distinctive vintage style of an abbreviated Chelsea boot set on a sturdy Goodyear welt sole.
Men's Lotus Gainsborough Wingtip Chelsea Boot
Now: $149.95 21% off
More Details Oversize broguing punctuates the wingtip and shaft of an updated Chelsea boot detailed with deep textured goring panels and a hearty lug sole.
Women's Dansko 'Marilyn' Midi Chelsea Boot
More Details Twin goring panels offer a comfortable, custom fit in this mid-cut boot while a round toe and chunky woodgrain sole make it feel like a clog. Pair it with your casual or dressier wardrobes for an effortlessly chic look.
Women's Valentino Rockstud Chelsea Boot
More Details Rockstud hardware shines at the sole of a sleek calfskin Chelsea boot, adding signature Italian glamour to the classic style.
Women's M4D3 'Felix' Chelsea Boot
Now: $95.96 40% off
More Details A streamlined profile and chunky rubber sole update a modern Chelsea boot with elastic-gore insets for a comfortable fit.
Women's Rieker Antistress 'Bernadette 94' Chelsea Boot
More Details A wraparound buckle strap adds a striking moto-chic element to a stacked-heel Chelsea boot featuring a lightweight, flexible sole for everyday comfort.
Women's Timberland Lakeville Chelsea Boot
More Details You won't have to sacrifice comfort for style (or vice versa) with this classic Chelsea boot featuring a rich suede finish and a SensorFlex™ system to ensure a smooth, stable ride. 4 3/4" shaft (size 8.5) OrthoLite® insole SensorFlex comfort system Leather and textile upper/textile lining/synthetic sole Imported Women's Shoes Helpful info: Boot Fit Fundamentals (video) , How to Measure Boots
Women's Sorel 'Addington' Waterproof Chelsea Boot
More Details This go-to Chelsea boot balances practicality with streetwise style, featuring a sturdy lugged sole and waterproof leather finish along with dynamically textured side panels and a sleek cap toe.
Women's Dr. Martens 'Eleanore' Chelsea Boot
More Details A sturdy lugged sole and textured leather finish reinvent a classic Chelsea boot with Dr. Martens' signature workwear attitude.