Chelsea boots are rooted in the Victorian era—the first boot was made by J. Sparkes-Hall for Queen Victoria. The story goes like this: Queen Victoria had requested a pair of boots without laces that she could wear while riding (laces got caught in her stirrups, which, I don’t ride, but sounds annoying?). The original boots were called “paddock” until the ’50s and ’60s when the name “Chelsea boots” came into the picture, thanks to its popularity in the United Kingdom and its association with the King’s Road (a street in the borough of Chelsea in London).
These days, Chelsea boots are beloved by everyone and have become an essential footwear style. So, what makes a Chelsea boot a Chelsea boot? Well, there’s typically a strip of black elastic that extends to just below the ankle, but not all the way down to the sole. The two parts of the boot are made from a single piece of leather (the vamp and the quarters). The vamp and the quarters meet near the ankle, where they are joined by a strip of vulcanized rubber or elastic. Ahead, classic and modern Chelsea boot styles that will make you fall in love with this shoe all over again.
Hunter Refined Slim Fit Quilted Gloss Chelsea Boots
Hunter’s waterproof glossy black Chelsea boots will seamlessly take you from day to night and ensure you won’t have to obsessively check the weather every hour.
Frye Melissa Chelsea Boot
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.
Koio Chelsea in Nero Boots
Expect to receive plenty of compliments whenever you throw on Koio’s bestselling Chelsea boots, which will instantly become a part of your capsule wardrobe.
Khaite Calgary Leather Chelsea Boots
Best paired with a midi skirt and cozy sweater or a beautiful dress, Khaite’s calgary leather Chelsea boots with two-inch heels are made to wear year-round.
Timberland Courmayeur Valley Chelsea Boots
If you still want to look cute while doing outdoorsy activities, throw on Timberland’s Chelsea boots, which are available in seven (!) different colors.
Everlane The Square Toe Chelsea Boot
Say hello to your new, sleek, square-toe Chelsea boot.
Loeffler Randall Bridget Embossed Leather Chelsea Combat Boots
Croc-embossed boots add a little something extra. Wear this style upper tucked into pant legs or alongside flowing midi dresses.
Staud Palamino Suede Chelsea Boots
The suede of these tan Chelsea boots will fit in with your autumnal wardrobe. Cue the pumpkin spice!
Sorel Brex™ Leather Chelsea Boots
Comfy? Yes. Durable. Check. These rugged Chelsea boots have a molded footbed and a can-do attitude—what more can you ask for?
FP Collection James Chelsea Boots
Two qualities I ask for in my Chelsea boots this season: The shoe has to have a thick platform and a heel, so my 5’4″ frame doesn’t look weighed down by my footwear. This pair from Free People is the answer.
Ganni Low Chelsea Leather Boots
Swap your traditional rain boots for this rugged Chelsea boot version.
Free People Atlas Studded Chelsea Bootie
No need to over-accessorize when your Chelsea boots come equipped with insets and studs like these.
Tory Burch Ivory Chelsea Boot
Take a chance on something new this season. These Tory Burch ivory Chelsea boots will look sharp with fall’s cozy knits and can be worn well into winter.
Thursday Boot Company Duchess Chelsea Boot
Expect compliments every time you slide on a pair of Thursday Boots’ Chelsea boots with its statement pull tab in the back.
Proenza Schouler Chelsea Boot
Contrast stitching and a stack lug sole merges outdoor sophisticated with everyday elegance.
Asgard Short Rain Boots Waterproof
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. I love a boot that does double duty.
Roger Vivier Viv Rangers Bootie
This is not your run-of-the-mill Chelsea. A burgundy patent leather exterior and a bold silver buckle kicks it up a few notches.
Dr. Martens 2976 Faux Shearling Chelsea Boot
These boots are designed to keep your feet warm on even the coldest of days. Dr. Martens’ boots are basically a winter essential, so it’s about time you got a pair for yourself.
Off-White Chelsea Leather Boot
Only Off-White can design a tag in the back that doesn’t take away from the shoe, or make you want to rip it off. This boot is perfect for someone who has an eye for designer goods, but doesn’t want something logo heavy.
Rag & Bone Rover Mid Heel Booties
If you’re looking for a boot that you can wear all year long, this pair is for you. Tan shoes really pop against the dark colors you wear during the fall and winter, and perfectly match any of your spring and summer outfits.
Diemme Alberone Chelsea Boots
Want added height without a heel? These boots by Diemme should do the trick. The sturdy sole will give you enough support for all-weather wear while adding on a few extra centimeters.
Proenza Schouler Topstitched Leather Chelsea boots
There’s no doubt the stitching on this shoe is what gives it the ultimate cool-girl look. It’s Proenza Schouler’s best-selling Chelsea boot, which means we all need it.
Marc Fisher LTD Yale Chelsea Boot
I can’t say enough great things about Marc Fisher’s pointy-toe Chelsea boots. They’re insanely comfortable and look great when you’re heading to those post-work drinks straight from the office.
Bells & Becks The Valentina Black Boot
Crafted from supple leather, this boot will mold to your foot, making it ideal for weekend looks but chic enough to pair with workwear too.