Women's Chelsea under $100



Brand: Skechers
Color: Chestnut
Smart, versatile style and athletic comfort combine beautifully in the Skechers Flex Appeal 2.0 Done Deal Sneaker Boot.

Brand: Aerosoles
Color: Black Leather
The must-have Aerosoles Double Trouble 2 Ankle Boot takes on the simplicity of the super-hot Chelsea boot and adds visible stitch and a squared toe detail. The hidden zipper closure gives you the sleekness of a Chelsea but with a lot more ease.

Brand: ED Ellen DeGeneres
Color: Lagoon
Charming critters run around this sleek rain boot in a classic Chelsea silhouette that's perfect for rainy days spent puddle jumping.

Brand: Sofft
Color: Barley Nomad
For a consistent on-trend look and promised durability, slip on the women's Sofft Selby Chelsea Boot. Featuring a leather or suede upper depending on your color choice.

Brand: Aerosoles
Color: Tan Suede
The must-have Aerosoles Double Trouble 2 Ankle Boot takes on the simplicity of the super-hot Chelsea boot and adds visible stitch and a squared toe detail. The hidden zipper closure gives you the sleekness of a Chelsea but with a lot more ease.

Brand: Linea Paolo
Color: Dark Taupe Suede
Western influences and classic Chelsea boot-inspired details combine on this contemporary leather bootie lofted by a stacked heel.

Brand: Steve Madden
Color: Mauve Suede
Breezy side cutouts refresh a Chelsea-inspired bootie styled with a gently rounded toe and elevated by a wrapped block heel.

Brand: Jack Rogers
Color: Multi Sparkle
This sleek rain boot channels classic Chelsea style with carefree, puddle-jumping ease.

Brand: Skechers
Color: Black
Top ranked comfort meets casual sporty style with the SKECHERS Flex Appeal 2.0 - High Card High Top.

Brand: roma
Color: Matte Red
A matte-finish Chelsea boot is made from natural rubber with quick-dry cotton lining to keep you feeling fashionable and comfortable even if the forecast calls for stormy weather.

Brand: COUGAR
Color: Black Diamond Welt
Add a little sparkle to gloomy days with this crystal-trimmed Chelsea boot crafted with a waterproof finish and an antislip EVA sole.

Brand: Jack Rogers
Color: Olive
This sleek rain boot channels classic Chelsea style with carefree, puddle-jumping ease.

Brand: KENDALL + KYLIE
Color: Black
Chic Chelsea boots refined with soft leather upper. Block heel, 2' (50mm).

Brand: Eastland
Color: Black
This chic chelsea boot has your casual style covered. Full grain leather upper.

Brand: dav
Color: Black
Stretchy, elasticized panels add Chelsea-inspired style to a waterproof, utilitarian boot grounded by a chunky heel and lugged sole.

Brand: FitFlop
Color: Black
Elastic goring panels provide slip-on convenience in a Chelsea boot-inspired sneaker with a low profile and a shock-absorbing SupercomFF midsole designed to diffuse pressure on your foot and provide flexible, all-day cushioning.

Brand: LEMON JELLY
Color: Black Gloss
A lemony scent adds to the the fresh, sleek style of a waterproof Chelsea boot that's made to keep you dry on rainy days.

Brand: FitFlop
Color: Desert Stone Suede
Gleaming buckle hardware adds moto edge to a comfortable Chelsea boot lofted by a sturdy wedge

Brand: Skechers
Color: Black
Mix smooth casual style with soft comfort easily with the SKECHERS Elm Ankle Boot. Smooth leather-textured microfiber fabric and sweater knit fabric upper in a slip on sporty ankle height casual comfort chelsea boot with Air Cooled Memory Foam insole.

Brand: Eastland
Color: Dark Walnut
This chic chelsea boot has your casual style covered. Full grain leather upper.

Brand: Dansko
Color: Green Rubber
The Dansko Rosa Chelsea Bootie is a versatile rain bootie that is a consistent wet weather essential. The Rosa is designed with a soft matte rubber upper that conforms to your feet, and elastic goring that lends flexibility and easy on/off wear.

Brand: Aerosoles
Color: Black Leather
The Aerosoles Stockholder Chelsea Boot is a style you won't be able to forget. It features a unique silhouette with an uber-sized, fully-covered block heel and double elastic goring.

Brand: Aerosoles
Color: Dark Brown Leather
The must-have Aerosoles Double Trouble 2 Ankle Boot takes on the simplicity of the super-hot Chelsea boot and adds visible stitch and a squared toe detail. The hidden zipper closure gives you the sleekness of a Chelsea but with a lot more ease.

Brand: Jeffrey Campbell
Color: Clear
Chelsea-inspired detailing adds a timeless touch to a cutting-edge boot designed to look stylish no matter the weather.

Brand: Jeffrey Campbell
Color: Glitter Multi
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.

Brand: MUK LUKS
Color: Gray
Fall in love with the MUK LUKS® Chelsea boot's stylish knit overlay and cute adjustable buckle accent. 50% acrylic and 50% polyester faux suede upper.

Brand: Cougar
Color: Black Rubber
The Kensington Waterproof Ankle Boot is a Chelsea boot inspired rain boot. The double gore makes pulling on and off easy, and a removable air mesh insole creates breathability.

Brand: Kenneth Cole New York
Color: Beige Multi Fabric
Velvety microsuede lends soft texture to a zipped-up high-top sneaker for a sporty take on the classic Chelsea boot silhouette.

Brand: Aerosoles
Color: Black Combo
The Tried and True Wedge Bootie from Aerosoles keeps you going throughout the day.

Brand: Cougar
Color: Surf Blue Rubber
The Terri Waterproof Chelsea Boot combines a sleek toe with a fun fashion heel so you can add a splash of color without getting wet! Anti-slip outsole Guaranteed waterproof.

Brand: Anne Klein
Color: Black Multi
Make a style statement wearing the Anne Klein Gorgia Chelsea Bootie. This captivating short boot shows off a chunky heel and a rear zipper closure for easy on and off.

Brand: Easy Spirit
Color: Black
Unpredictable weather and cooler temperatures mean it's time to wear Easy Spirit's water-resistant Chelsea bootie. Water-resistant suede leather upper.

Brand: G.H. Bass & Co.
Color: Black Suede
Slip into style and comfort with the G.H.

Brand: G.H. Bass & Co.
Color: Cloud Grey Suede
Slip into style and comfort with the G.H.

Brand: Teva
Color: Pecan Leather
A hip-and-relaxed version of the classic Chelsea boot, the Teva Willow Chelsea Sneaker offers laidback style and premium comfort. Double-gore slip-on Soft and luxurious pig skin lining Cushioning footbed for comfort and shock-absorption Rubber outsole.

Brand: Sole Society
Color: Taupe
A stacked block heel updates the look of a chic bootie made with tonal Chelsea-style insets for easy on and off.

Brand: Dr. Scholl's
Color: Stucco Microsuede
For a refined look, step into Dr. Scholl's Jorie Chelsea Boot.

Brand: roma
Color: Black Croc
A matte-finish Chelsea boot is made from natural rubber with quick-dry cotton lining to keep you feeling fashionable and comfortable even if the forecast calls for stormy weather.

Brand: Dkny
Color: Black Leather
Dkny Talie Chelsea Booties, Created For Macy's Shoes

Brand: roma
Color: Kale
A little rain won't put a damper on your style thanks to this glossy rain boot featuring decorative laces and a classic Chelsea-inspired silhouette.

Brand: Jeffrey Campbell
Color: Black Matte
A Chelsea-style rain boot lifted by a chunky block heel keeps you looking stylish and chic, whatever the weather.

Brand: Sakroots
Color: Black White Spirit Desert
Vibrantly patterned neoprene forms the gore insets of a Chelsea-inspired waterproof rain boot fitted with a crocheted pull loop and set on a traction-enhancing lugged sole.

Brand: Hunter
Color: Black
Invest in a pair of Hunter's iconic rubber wellingtons - our favorite is this sleek Chelsea silhouette. In classic black with pull-on tabs on either side, they'll look good in both the sun and rain.

Brand: Timberland
Color: Medium Brown Leather
Timberland updates the essential Chelsea bootie with deeply scooped goring that wraps around the front of the shaft for an especially comfortable, flexible fit. The OrthoLite Mirror Fit footbed and Defender water-resistant treatment help keep your feet comfy and dry all day.

Brand: Sam Edelman
Color: Black Matte PVC
Time to brave the elements with the Sam Edelman Tinsley Rain Bootie! Stay dry in style with this classic rain boot in a sophisticated Chelsea boot silhouette.

Brand: Indigo Rd
Color: Blue
This charming Chelsea ankle boot has a romantic vibe to it. Floral-embossed velvet upper.

Brand: Sole Society
Color: Brown
Classic Chelsea styling defines a trend-right suede bootie lifted by a walkable block heel.

Brand: G.H. Bass & Co.
Color: Wine Suede
Slip into style and comfort with the G.H.

Brand: Cougar
Color: Port Rubber
The Kensington Waterproof Ankle Boot is a Chelsea boot inspired rain boot. The double gore makes pulling on and off easy, and a removable air mesh insole creates breathability.

Brand: Heal USA
Color: Black
Designed with the active, fashion-forward woman in mind, the Audrey boot from Heal USA features a Chelsea boot style combined with their signature hand-woven upper. These mid-sized wedge heels enhance your look while keeping your feet comfy.