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 that 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 classic Chelsea boot styles as well as trendy iterations that will make you fall in love with this shoe all over again.
For an alternative to your short, Chelsea ankle boot styles, go with this tall shaft version. It's great for wearing underneath long fall dresses or tucked underneath your cropped jeans. The chunky sole is on trend for the season.
Prefer your ankle boots with a bit of fluff for warmth? These faux fur lined Dr. Martens will keep your ankles feeling cozy and your feet cushioned thanks to the supportive footbed.
You're maxed out on black Chelsea boots, I get it. So opt for this dewy green pick from Ganni instead. It's made from 100 percent recycled rubber and can hold its own, and you, against slushy, icy streets.
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.
Two qualities I ask for in my Chelsea boots this season: It 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.
Even the pickiest shopper will fall for these classic Chelsea ankle boots in a wearable shade of tan. The boots are made in Italy and also come in black if you want a darker hue.
Fans of Stutterheim rain coats will want to finish up their outfits with a pair of Stutterheim rain boots. This low ankle style, complete with the brand's name on the side, are cute and functional.
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.
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.
You might not be a big fan of bourbon (you're a vodka type of gal), but you may fall in love with the bourbon color on this chunky bootie. They're the boots to wear when you're on a mission to conquer your to-do list.
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.
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.
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.
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.
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.
This ankle boot is water resistant, which is great news for those who perpetually forget their umbrellas at home.
This easy-to-wear boot was made in Portugal and features cool details like a croc embossed look and a rounded toe for those of you who are square toe-adverse.
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 matches everything.
I love a good houndstooth print and if you do as well, you'll be smart, and trendy, to opt for this Chelsea boot silhouette from Stuart Weitzman. It comes embellished with faux pearl details along the welt too! Fancy.
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.
If you're not a fan of the chunky sole Chelsea boots this season, check out this sleek heeled shoe. The three different neutral tones are wearable and look statement-worthy when combined together.
For a "look at me" boot, you'll 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.
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.
I know we've been focused on tall Chelsea boot styles, so here's one with a lower shaft you can just easily slip on and go. This boot has "fluidform" technology, which means it absorbs shock from the ground and provides a comfy cushion as you walk.
For the ultimate classic American Chelsea rain boot, you'll need to grab this one from Ralph Lauren. The splash of red and glossy finish are beautiful touches to the footwear.
This cream-colored Chelsea boot is made in Italy from vegetable-tanned leather with a wavy black rubber midsole and transparent rubber tread sole. Never have I seen such a complex and richly detailed bootie. Need.
Say goodbye to traditional rainboots and swap them with these glossy waterproof chelseas. You'll want to wear them even when it's not monsooning outside. Trust.
Expect lots of compliments every time you slide on a pair of Thursday Boots' chelsea boots with the statement pull tab in the back.
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.