Courtesy of Steve MaddenChelsea boots have been around forever. They've been worn by everyone from The Beatles to Kendall Jenner.
Although Chelsea boots have evolved, they’re just as stylish and timeless as they’ve always been. No matter what form they take, the classic Chelsea boot is the winter shoe that will never let you down.
The ankle boot comes in every heel height, material, and style you can think of, and pair well with everything from tailored trousers to barrel jeans.
Wear a trendy brown suede pair with a fair isle sweater or go for sleek leather black boots with cigarette jeans and a cropped trench. And rock a heeled style with a dress for an edgy yet sweet look. Either way, you’ll look effortlessly chic.
Whether a pair of block heel booties or ones with a chunky rubber sole, now's the perfect time to grab a pair for less, because so many brands are running Black Friday and Cyber Monday sales right now. Think Dr. Martens, UGG, Sam Edelman, Dolce Vita, Steve Madden, Aldo and more.
Find your perfect pair. Shop the best Chelsea boots, starting at $40.
Cestfini Outdoor Chelsea Hiking Boots
If you don't want to drop over $200 on a pair of Blundstones, get these affordable alternatives instead. Waterproof and slip-resistant, these rugged leather work boots have an easy-on, easy-off slip-on design and will look great styled with a trendy barn jacket.
Dr. Martens 2976 Chelsea Boot
These Dr. Martens Chelsea boots are an absolute classic— and will become your go-to winter shoe. Made from a soft leather that requires a minimal break-in period, these boots have a lugged sole and the iconic yellow stitching Docs are known for.
Quince Italian Leather Heeled Ankle Boot
These versatile ankle booties easily transition you from desk to dinner. Made from premium Italian leather, their sleek silhouette and short block heel will never go out of style.
Steve Madden Blitzen Platform Chelsea Boot
Chelsea boots with suede uppers? That's a match made in shoe heaven. This pair got a modern update with a chunky lug sole and a taller shaft featuring stretchy panels that makes them easy to take on and off.
Dolce Vita Shadie Waterproof Pointed Toe Chelsea Boot
A pointed toe and angled block heel give these Chelsea boots a Western flair. The chestnut-hued suede uppers make it the quintessential fall (and Thanksgiving) shoe.
UGG Women's Moxy Chelsea Boot
Ugg always brings the cozy vibes, and their trendy take on the Chelsea boot is no different. This eye-catching pair has ribbed sock-like detailing and is made from water-resistant suede.
Sam Edelman Laguna Chelsea Boot
This pair boasts a utilitarian style, yet still manages to look incredibly sophisticated no matter what you wear them with. They combine a classic Chelsea boot silhouette with a modern lug sole.
Aldo Anneliese Boot
These boots perfectly toe (pun intended) the line between casual and elevated. They're designed with Aldo's cloud-like Pillow Walk insoles and have a warm lining to keep your feet warm in the winter.
Michael Kors Lex Leather Boot
Looking for a chic minimalist option to add to your wardrobe? These streamlined leather boots with an almond toe are just the thing. This block heel pair (which has a convenient interior zipper) can be worn with jeans and dresses.
Dr. Martens Spence Leather Flared Heel Chelsea Boot
If you love the Dr. Martens Chelsea boot but wish they had a heel, you're in luck because these bad boys exist. Made from the same weather-resistant materials Docs are known for, they boast a stacked platform heel that gives an edgy look to a mini dress and tights.
Yes, barrel jeans are still in! We found 10 styles under $50.