Did you know that the first Chelsea boot (one of my all-time favorite types of boots) was made for Queen Victoria? The story goes like this: Queen Victoria had requested a pair of boots without laces so that she could wear while riding, explaining that laces tended to get caught in her stirrups (which, I don't ride, but sounds annoying?). As a result, London-based shoemaker J. Sparkes-Hall designed the now-classic boots, which were called "paddock" until the '50s and '60s when their name morphed into "Chelsea boots," thanks to the style's association with King's Road, a street in London's borough of Chelsea. These days, Chelsea boots have gone beyond their British roots and become a universal favorite.
"Chelsea boots are a fall staple," agrees celebrity stylist and costume designer Alexandra Imgruth, who explains that these accessories are, on a basic level,
"flat ankle boots easily spotted by their elastic side panel." Indeed, this style is made from a single piece of leather, split into two parts called the vamp and the quarters. These parts meet near the ankle, where they're joined by a strip of vulcanized rubber or elastic that extends just below the ankle but stops before reaching the sole.
Ahead, check out some of the very best Chelsea boots for women in 2023, from classic to modern, that are sure to make you fall in love with this classic fall boot all over again.
Best Chelsea Boots
- Best Overall Chelsea Boots: Crockett and Jones Bonnie Chestnut Burnished Calf
- Best Cuban Heel Chelsea Boots: Bandolino Dattie Bootie
- Best Weather-Proof Chelsea Boots: Hunter Refined Slim Fit Quilted Gloss Chelsea Boots
Not only are these boots chic, but, according to reviews, they're incredibly comfortable. One highly satisfied customer writes, "I’m sitting on the sofa watching TV [with them on] because I don’t want to take them off."
When we asked Imgruth about her go-to pair of Chelsea boots, she said, "As they're inherently English, it's always best to get it from the source—an English brand. My favorite is Crockett and Jones."
These Chelsea boots have a matte finish and are suited for rainy days, though you can wear them even when there's not a cloud in the sky. Plus, they're so comfortable that one reviewer says they feel "like house slippers." It's no wonder they're #1 bestselling women's rainboots on Amazon!
This beautiful wedge pair is, by all accounts, comfortable, easy to slip on, and true to size. One review notes that they "hold up really well through all weather" and that they provide substantial arch support.
Imgruth reminds us that a heeled Chelsea boot—a "low heel with a tapered back and straight front"—is commonly known as a Cuban heel. This pair is chic and matches with everything, and it even features a gold embellishment to spice your outfit up.
If you're a fan of the Cuban heel, Imgruth suggests this "perfect" pair from Celine, which balances its sleek, feminine shape with a touch metal toe.
Hunter's waterproof boots will seamlessly take you from day to night and ensure you won't have to obsessively check the weather every hour. Reviewers say that they're warm, true to fit, and "the perfect height and weight"—a hard balance to strike in the world of rain boots. And if you're in the mood to customize, take advantage of the fact that these come in ten different colors!
Come for the durability of Frye's vintage Italian leather booties, stay for the gorgeous redwood color they come in that will stand out from the rest of your Chelsea boot collection. Customers rave that these boots are true to size, long-lasting, and don't even require a "break-in period."
Expect to receive plenty of compliments whenever you throw on Koio's bestselling Chelsea boots, which will instantly become part of your capsule wardrobe. Indeed, several reviews call this pair their new "everyday boot," with one satisfied customer explaining that the certified Italian leather "molds to your foot and is so soft."
Animal prints, like this croc-embossed look, give your 'fit what Imgruth calls a "more experimental look." Try this style tucked beneath a pair of jeans or with a flowing midi skirt.
Imgruth also cites "a beautiful suede" option, like this pair from Staud, as one of her Chelsea boot go-to's. The pair also features an elastic cuff, so you can look good in maximum comfort.
These boots come in seven different colors, and customers rave about how high-quality they look and how easy they are to walk in. They do run small, though, so be sure to round up if you're between sizes!
I love a good pointed-toe boot, and this gorgeous option is, in the words of one pleased customer, "that rare balance of style and comfort in a single item [which] is hard to find."
Looking for Chelsea boots that make an unforgettable statement? Check out this pair from Bottega Veneta. Made from high-quality leather with rubber soles, they promise a comfortable, snug fit suitable for getting you through the day in optimal comfort and style.
According to reviews, these rain boots are both compliment-inducing and cozy. Multiple customers say that this pair keeps their feet (especially their toes!) warm during the winter months, and that it keeps them dry during even the most brutal winter storms.
Meet the Expert
Alexandra Imgruth is a fashion stylist and style consultant who works with celebrities and priavte clients alike. She is currently based in New York City.
