The 16 Best Chelsea Boots to Add to Your Winter Wardrobe
Come winter, I'm never not dreaming about buying a new pair of boots. And as any typical shopping editor would, I already have a few silhouettes on my radar this season that I'm hoping to either be gifted for the holidays (hint hint, to any of my loved ones) or invest in for myself just in time for the new year. The style at the very top of my wishlist? Chelsea boots, of course. These cool and classic shoes double as the perfect everyday boots that pretty much always look good. Plus, thanks to the style's durable composition and build, Chelsea boots are also ideal for rainy weather and winter temperatures.
There are also so many different variations of the shoe — from varied colors like brown and white Chelsea boots to leather Chelsea boots, waterproof styles that can withstand the season's harshest weather, and even a few chunky Chelsea boots that can make any winter outfit all the more eye-catching, the options are truly endless.
To help you find the perfect match, we scoped out the best Chelsea boots for women that are not only trending for winter, but also available to shop from some of our favorite fashion brands like Sam Edelman, Hunter, Steve Madden, Blundstone, Dr. Martens, and more. Ahead, we curated a list of 17 Chelsea boots that you'll love to wear in any season. Whether you're looking for something edgy like a pair of black leather Chelsea boots, something practical and easy to walk in like a comfortable pair of Chelsea boots, or perhaps even something that will help to add a fresh pop of color to your winter wardrobe like a pair of pink Chelsea boots, there's bound to be a style out there that's just perfect for you. Keep reading to shop our selects and find the perfect boot for you.
— Additional reporting by Krista Jones
Best White Chelsea Boots For Women: Cushionaire Perry Slip-On Chelsea Boot
Black Chelsea boots be damned — this Cushionaire Perry Slip-On Chelsea Boot ($40) might just take the cake as the go-to shoe to have this winter. Not only does the style ooze a sort of retro, Y2K-inspired aesthetic, but it's also refreshingly comfortable, too — provided by the boot's cushiony sole, of course.
Best Rain Chelsea Boots For Women: Hunter Commando Chelsea Boots
Rain or shine, these Hunter Commando Chelsea Boots ($124) will have you covered. The comfortable Chelsea boot is crafted from a durable rubber sole material that can withstand even the harshest outdoor weather conditions. We love the boot's breezy, slide-on design and the fact that it's available to shop in a variety of colors. Plus, one POPSUGAR editor even claimed the timeless rain boot was "worth the splurge" in this review on the Hunter Commando Chelsea Rain Boots.
Best Editor-Loved Chelsea Boots For Women: Dr. Martens 2976 Chelsea Boot
This Dr. Martens 2976 Chelsea Boot ($150) is hailed for being one of the best Chelsea boots by fashion-lovers and POPSUGAR editors alike — just read our review on the Dr. Martens Zip Chelsea Boots for further proof. The ankle boot is crafted from a durable, bovine leather material that's as long-lasting as it is totally chic, too.
Best Pink Chelsea Boots For Women: Circus by Sam Edelman Darielle Bootie
Black Chelsea boots might get all the hype and attention, but we're big believers in colors. And if you're looking for a statement-making shoe that can elevate even the most muted outfit, you can't go wrong with this light pink Circus by Sam Edelman Darielle Bootie ($70, originally $100). The Barbiecore aesthetic is predicted to trend well into 2023, and you'll be so ahead of the fashion game with this pink Chelsea boot on hand.
Best Comfortable Chelsea Boots For Women: Steve Madden Hayle Platform Chelsea Boot
In terms of the best Chelsea boots to have incorporated into your wardrobe (or really any boot style for that matter), you can never go wrong with Steve Madden. The brand has so many chic and practical booties to choose from, like this Steve Madden Hayle Platform Chelsea Boot ($100), which boasts a chunky platform and a stretchy, ribbed material along the heel. Bonus: the boot is also available in three colors!
Best Waterproof Chelsea Boots For Women: Hunter Original Chelsea Boots
Rainy days are perfect for these Hunter Original Chelsea Boots ($165). The black, chunky Chelsea boots boast an updated silhouette in a sleek and totally versatile shade that provides so much styling opportunity. Plus, it's basically like getting two boots in one with this hybrid Chelsea-boot and rain-boot style.
Best Chunky Chelsea Boots For Women: Bottega Veneta BV Tire Boots
These Bottega Veneta Tire Boots ($1,450) are going to be the shoe of the season, so snag yours while you can. Sure, the price tag is admittedly a pretty hefty one, but if you're looking for a pair of designer Chelsea boots, we'd argue it doesn't get any more eye-catching than this style. Plus, the color-block sole is so unique.
Best Chelsea Boots For Walking: Timberland Cervinia Valley Chelsea Boot
Looking for something durable and long-lasting? Look no further than this Timberland Cervinia Valley Chelsea Boot ($100, originally $160). Reviewers hail this boot for its comfortable sole, breathable base material, and style versatility — seriously, you can wear it with anything, and it looks so good. Theese brown Chelsea boots also have a thick fabric lining along the base, making them even more ideal to wear in the fall and winter seasons.
Best Designer Chelsea Boots For Women: Ganni Chelsea Boot
This Ganni Chelsea Boot ($445) is a modern take on the classic style, and it's high on our wish list. The bright color inserts make it stand out with more of a rugged and edgy flair. And that army-green coloring is simply divine – especially for the winter!
Best Overall Chelsea Boots For Women: Sam Edelman Laguna Chelsea Boot
It's likely you've seen this Sam Edelman Laguna Chelsea Boot ($100, originally $170) splashed across your Instagram or TikTok at some point — and for good reason. The boot became especially popular last fall thanks to its durable, lug-sole design, and ultrachic maroon coloring. The chunky Chelsea boot's silhouette is also super unique, with a height that falls between an ankle bootie and a knee-high Chelsea boot style.
Best Chelsea Boots For Wide Feet: Blundstone BL2143 Active Chelsea Boot
The best Chelsea boots are shoes that are equal parts stylish and comfortable — just like this Blundstone BL2143 Active Chelsea Boot ($230). Between the arched silhouette and added stretch panels, we can't get over how sneaker-like this Blundstone Chelsea boot is. With its sporty design, this may be the Chelsea boot to opt for in any season.
Best Black Leather Chelsea Boots For Women: Vagabond Shoemakers Jillian Chelsea Boot
Meet your new everyday shoe: the Vagabond Shoemakers Jillian Chelsea Boot ($200). From the laidback profile to the modern square-toe silhouette, everything about it screams effortless style. And unlike more popular Chelsea boot styles, we love that this pair oozes a blurred, matte design.
Best Platform Chelsea Boots For Women: Last Powder Chelsea Boots
We love all the details on these cool Last Powder Chelsea Boots ($300). Not only are you likely to turn heads in any room with these cream Chelsea boots on, but we're also confident your friends will be asking where you got them from, too. And can you blame them? That color-block design is so cool and unique.
Best Leather Chelsea Boots For Women: Everlane The Italian Leather Chelsea Boot
You can never go wrong with having a classic pair of white Chelsea boots in your wardrobe — especially if they're as elegant as this Everlane The Italian Leather Chelsea Boot ($195). Available in two colors, the suede Chelsea boot features elastic side panels (for added comfort) and a stylish round-toe design.
Best Brown Chelsea Boots For Women: Loeffler Bridget Dark Brown Lug Boot
This fun Loeffler Bridget Dark Brown Lug Boot ($395) doesn't just look stylish — it's also practical. Slip it on no matter the weather, and we're confident you won't regret it. Plus, if you're looking for a more unique pair of textured Chelsea boots, you'll appreciate that this style is wrapped in a patent-croc design that's so effortlessly cool and on trend.
Best Outdoor Chelsea Boots For Women: Blundstone 500 Chelsea Boots
If you're in the market for a go-anywhere shoe that you can wear while you're adventuring outdoors or simply running daily errands, you can't go wrong with owning a pair of Blundstone Chelsea boots — especially if they're as rustic and stylish as these Blundstone 500 Chelsea Boots ($210). The athletic shoe also doubles as one of the best Chelsea boots for people with wide feet, thanks to its relaxed design.