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21 Chelsea Boots You'll Fall In Love With

Bring it on, cold weather.

chelsea boots
Courtesy of the brands

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.

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The Square Toe Chelsea Boot
Courtesy of Everlane
Everlane everlane.com
$195.00

Say hello to your new, sleek, square-toe Chelsea boot. 

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Bridget Embossed Leather Chelsea Combat Boots
Courtesy of Loeffler Randall
Loeffler Randall saksfifthavenue.com
$395.00

Croc-embossed boots add a little something extra. Wear this style upper tucked into pant legs or alongside flowing midi dresses.

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Ridley Leather Chelsea Booties
Courtesy of Michael Michael Kors
MICHAEL Michael Kors saksfifthavenue.com
$131.25

The Chelsea boot's edgy twin. The cutout heel will add a subtle flare to an otherwise basic look.

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Palamino Suede Chelsea Boots
Courtesy of Staud
Staud saksfifthavenue.com
$425.00

The suede of these tan Chelsea boots will seamlessly fit in with your autumnal wardrobe. Cue the pumpkin spice!

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Brex™ Leather Chelsea Boots
Courtesy of Sorel
Sorel saksfifthavenue.com
$160.00

Comfy? Yes. Durable. Check. These rugged Chelsea boots have a molded footbed and a can-do attitude—what more can you ask for?

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High-Heel Chelsea Boot
James Chelsea Boots
FP Collection freepeople.com
$188.00

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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Low Chelsea Leather Boots
Courtesy of Ganni
Ganni saksfifthavenue.com
$425.00

Swap your traditional rain boots for this rugged Chelsea boot version. 

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Atlas Studded Chelsea Bootie
Courtesy of Free People
FREE PEOPLE nordstrom.com
$148.00

No need to over-accessorize when your Chelsea boots come equipped with insets and studs like these.

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Ivory Chelsea Boot
Courtesy of Tory Burch
Tory Burch nordstrom.com
$428.00

Take a chance on something new this season, they'll look sharp with fall's cozy knits and can be worn well into winter.

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Gray Chelsea Boot
Duchess Chelsea Boot
Thursday Boot Company amazon.com
$160.00

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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Chelsea Boot
Courtesy of Proenza Schouler
Proenza Schouler nordstrom.com
$825.00

Contrast stitching and a stack lug sole merges outdoor sophisticated with everyday elegance.

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Classic Black Chelsea Boot
Short Rain Boots Waterproof
Asgard amazon.com
$27.99

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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Viv Rangers Bootie
Courtesy of Roger Vivier
ROGER VIVIER saksfifthavenue.com
$1,325.00

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.

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Fur-Lined Chelsea Boots
2976 Faux Shearling Chelsea Boot
Dr. Martens nordstrom.com
$160.00

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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Off-White Chelsea Leather Boot
Courtesy of Off-White
Off-White bluefly.com
$583.99

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
$378.00

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
$425.00

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
$131.67

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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Platform Chelsea Boot
Alberone Chelsea Boots
Diemme shopbop.com
$449.00

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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Cult-Favorite Chelsea Boot
Topstitched Leather Chelsea boots
Proenza Schouler matchesfashion.com
$553.00

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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Snake Print Chelsea Boot
Yale Chelsea Boot
Marc Fisher LTD nordstrom.com
$119.90

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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