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28 Chelsea Boots You'll Fall In Love With

I'm ready for winter!

chelsea boots

Chelsea boots are rooted in the Victorian era, which is when the first boot was made by J. Sparkes-Hall for Queen Victoria. The story goes: 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 awfully 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, not just people in the UK, and have become an essential footwear style everyone should own. The typical traits of the boot include 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. Enough history and semantics, though, I know you came here to shop fall/winter 2020's best Chelsea boot selections. Ahead are 28 classic Chelsea boot styles as well as trendy iterations that will make you fall in love with this shoe all over again.

Gray Chelsea Boot
Duchess Chelsea Boot
Thursday Boot Company amazon.com

Expect compliments every time you slide on a pair of Thursday Boots' Chelsea boots with its statement pull tab in the back. 

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Classic Black Chelsea Boot
Short Rain Boots Waterproof
Asgard amazon.com

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.

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Fur-Lined Chelsea Boots
2976 Faux Shearling Chelsea Boot
Dr. Martens nordstrom.com

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 one for yourself. 

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High-Heel Chelsea Boot
James Chelsea Boots
FP Collection freepeople.com

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 to my search.

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Luxe Chelsea Boot
Logo Patch Chelsea Boots
Off-White farfetch.com

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. 

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Cushioned Footbed Chelsea Boot
Natasha Water Resistant Chelsea Boot
Paige nordstrom.com

A good alternative to wearing heels in the winter, if you like height in your footwear, is to slip into this boot from Paige. It has a 3-inch heel and 1.5-inch platform, so you can feel comfortably elevated amongst your peers.

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Tan Chelsea Boot
Rover Mid Heel Booties
rag & bone bloomingdales.com

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. 

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Clear Sole Chelsea Boot
The Stomper Boots
The Marc Jacobs shopbop.com

A translucent sole gives these otherwise simple boots a modern twist. The higher rise on the ankle will keep your feet dry as you stomp your way through the winter season. 

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Edgy Chelsea Boot
Natina Booties in Black Box Leather
Dolce Vita dolcevita.com

When selecting a pair of Chelsea boots, don't forget to look for unique details that make it different. This pair has silver hardware wrapped around the heels for a edgy finish.  

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Leather Chelsea Boot
Sarto Freda Chelsea Boot
Franco Sarto zappos.com

This chunky Chelsea boot is a more affordable alternative to your favorite designer pairs if you're on a budget. The leather and hard sole makes the shoe look luxurious and cool. 

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Animal-Free Chelsea Boot
Chunky Chelsea Boots
Stella McCartney farfetch.com

For fans of Stella McCartney and those looking for vegetarian and animal-free alternative footwear, you'll want to scoop up this Chelsea boot from the designer. My favorite details are the visible stitching and the white rigid rubber soles. 

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Suede Chelsea Boot
Henderson Weatherproof Chelsea Boot
Vince nordstrom.com

When you find your dream Chelsea boot, you best buy a few more colorways too if possible. This pair comes in several hues, which means you're set in finding a pair that matches all your fall/winter outfits. 

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Platform Chelsea Boot
Alberone Chelsea Boots
Diemme shopbop.com

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. 

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Affordable Chelsea Boot
Dasha Chelsea Boot
Sam Edelman nordstrom.com

I've always been a fan of Sam Edelman shoes for both its affordability and quality. I have a few boots from the label already, but I'm definitely keeping my eye out to add this Chelsea boot to my shoe collection.

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Everyday Chelsea Boot
Kenova Tall Chelsea Boot
Vagabond Shoemakers urbanoutfitters.com

I can find no fault with this Chelsea boot. It's a good option to invest in if you're looking for a simple, everyday shoe. There will be no second guessing what it matches with because it goes with everything. 

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Waterproof Chelsea Boot
Harlow Chelsea
Sorel zappos.com

Here's another waterproof Chelsea boot to check out. Sorel is known for making comfortable shoes, so you can trust this ankle boot will keep your toes dry and cushioned for your long (short?) walks in the rain.

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Pearl Embellished Chelsea Boot
Faux Pearl-Embellished Chelsea Boots
Dolce & Gabbana farfetch.com

For a "look at me" boot, add these D&G booties to your checkout cart asap. The giant pearls look like they were dropped from above and landed perfectly in line on your shoe. Also, make sure to note the little "DG" gold logo on the side of the heel.

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Cult-Favorite Chelsea Boot
Topstitched Leather Chelsea boots
Proenza Schouler matchesfashion.com

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 I, you, everyone, need it.

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Green Chelsea Boot
The Rain Boot
Everlane everlane.com

Olive green is a neutral, right? These boots from Everlane retail for under $100 and offer protection from bad winter weather while looking totally cute at the same time. A.k.a.: they're perfect. 

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Tall Chelsea Boot
Andee Chelsea Boot
Alexander Wang nordstrom.com

These are like the regular Chelsea boot's edgy twin. The height on their ankle makes them perfect to tuck your trousers into, and the cutout heel detail adds a subtle bit of flair to even your most basic look. 

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Cutout Chelsea Boot
Caring Chelsea Boot
CL by Chinese Laundry amazon.com

Cheetah print makes any item of clothing more fun, and these boots are no exception. Even better, the ankle cutout detailing make them way more fun (and fashionable) than your usual black boots. 

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Quilted Chelsea Boot
Women's Refined Slim Fit Quilted Gloss Chelsea Boots
Hunter hunterboots.com

Say goodbye to traditional rain boots and swap them with these glossy waterproof Chelseas. You'll want to wear them even when it's not monsooning outside. Trust. 

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Snake Print Chelsea Boot
Yale Chelsea Boot
Marc Fisher LTD nordstrom.com

I can't say enough great things about Marc Fisher's pointy-toe Chelsea boots, which come in nine (!) different styles. They're insanely comfortable and look great when you're heading to those post-work drinks straight from the office. Pick the ivory or snakeskin if you want a pair you can wear year-round. 

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Croc Chelsea Boot
Chelsea Embossed Ankle Booties
Freda Salvador bloomingdales.com

Croc-printed boots add a little something extra to your all-black look. These boots from Freda Salvador come in an evening-appropriate glossy leather, so you can wear them any time of day (or night). 

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Studded Chelsea Boot
Studded Chelsea boots
Love Moschino farfetch.com

Studs add edge, but they also can look quite delicate. Case in point: these boots by Love Moschino. Match your accessories to the studs and you'll look super put together in no time. 

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White and Black Chelsea Boots
Painter Lug Sole Booties
Villa Rouge shopbop.com

Don't panic—white boots are totally wearable in the winter. Not only are they super easy to clean, but they go with everything. The stark black detailing on this particular pair should give you all the reason you need to take a chance on something new this season. 

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Brown Chunky Chelsea Boot
Trap Chelsea Boot
Steve Madden dsw.com

You might not be a big fan of cognac (you're a vodka type of gal), but you may fall in love with the color on this chunky bootie. They're the boots to wear when you're on a mission to conquer your to-do list. 

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Knit Chelsea Boot
Silko Smocked Boot
Louise et Cie nordstrom.com

If you're on the hunt for a Chelsea boot that is tight on the ankle, look no further—we've found the perfect one. These boots from Louise Et Cie is will work seamlessly under wide-leg trousers and skinny jeans alike thanks to their slim, high ankle design. 

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