Chelsea boots have long been a wardrobe staple, in our opinion, but the relatively recent rise in comfort-forward fashion (Dad sneakers, Normcore, Cabincore, etc.) has turned these comfortable ankle boots into an absolute must-have. They’re incredibly easy to wear, never go out of style and come in enough varieties to justify owning multiple pairs. But for those looking for the absolute best of the best, either to expand on an already existing collection or to try Chelsea boots for the very first time, this list is a good place to start. But first, a little history lesson…
The Best Chelsea Boots for Women, Starting at $53
PureWow editors select every item that appears on this page, and the company may earn compensation through affiliate links within the story. You can learn more about that process here.
What Are Chelsea Boots, Exactly?
Named for the Chelsea neighborhood of London where they first became popular, Chelsea boots are typically a simple ankle boot that includes a stretchy gusset on the side so you can pull them on and off without a zipper or shoelace. The style actually dates back to the Victorian era (Queen Victoria herself was reportedly a huge fan), but was brought back into the zeitgeist in the ‘60s when Mod fashionistas, both men and women, revived them. And after The Beatles started wearing them, there was simply no going back.
What’s the Best Way to Wear Chelsea Boots?
Part of the reason the Chelsea boot is so popular is that it goes with just about anything and everything—minidresses, raw-hem jeans, tailored suits, even slinky slip dresses. You can wear them so many different ways, and they aren’t linked to any specific generation (unlike Crocs or skinny jeans), so everyone can get in on the fun. If you’re unsure where to start, try something classic and simple like dark-wash jeans and a white button-up shirt for a no-fail look that’s appropriate for whatever you may have on your schedule.
Read on for the absolute best Chelsea boots for women that money can buy.
Best Chelsea Boots for Women at a Glance
- PureWow Reader Favorite: Caslon Miller Water-Resistant Chelsea Boots
- Best Platform: Dr. Martens 2676 Platform Chelsea Boots
- Best Heeled Chelsea Boots: Naturalizer Mindy Waterproof Booties
- Best Under $100: Crown Vintage Tipryn Chelsea Boots
- Most Splurge-Worthy: Frances Valentine Gem Boots
- Most Practical: Blundstone 510 Chelsea Boots
- Most Comfortable: Marc Fisher LTD. Padmia Chelsea Boots
- Best for Wide Feet: ASOS Wide-Fit Appreciate Chelsea Boots
- Best Rain Boots: L.L.Bean Rugged Wellie Chelsea Boots
- Best for Winter: Dr. Martens 2976 Faux-Fur Lined Chelsea Boots
- Best White Chelsea Boots: Everlane Italian Leather Chelsea Boots
- Best Neutral That Isn’t Black: Sam Edelman Laguna Waterproof Pull-On Booties
- Best Minimalist Design: Nisolo Everyday Chelsea Commuter Boots
- Best Sustainably-Made Boots: Reformation Katerina Lug-Sole Chelsea Boots
- Trendiest Designer Pick: Bottega Veneta Tire Chelsea Boots
- Best Designer Look for Less: ASOS Raindrop Chunky Chelsea Boots
1. Caslon Miller Water-Resistant Chelsea Boots
PureWow Reader Favorite
This simple water-resistant bootie by Caslon has sold out numerous times since hitting Nordstrom’s site a little over a year ago, and a large part of that is because of PureWow’s very own. Readers have proclaimed them incredibly comfortable, weather-resistant and surprisingly durable given their $100 price tag (though they’re currently on sale for just $70). They also come in burgundy faux-leather and beige and moss green faux-suede. If you haven’t already jumped on the bandwagon, we think now is the time to do so.
2. Dr. Martens 2676 Platform Chelsea Boots
For those looking for a little height boost that won’t stress your arches like a true high heel, opt for this Dr. Martens platform boot. (And, yes, it also comes in black.) It’s one of the brand’s most classic silhouettes, and the exaggerated lug sole adds 2-inches without looking overly chunky. “I think these are the perfect mix of a classic look and an edgier fashion forward style,” says one happy shopper. “They’re great if you are trying to go for a Dr. Martens look, but maybe a little more mature or less punk.” The only downside is that these boots come in only whole sizes. Reviewers suggest those who are between sizes should opt for the smaller, unless you have wide feet, in which case go for the larger.
3. Naturalizer Mindy Waterproof Booties
Best Heeled Chelsea Boots
If you’re after a true heel, this Naturalizer pair was designed in conjunction with a team of podiatrists to ensure your feet get the support they need even with that 2 ¾-inch heel. The Mindy is also entirely waterproof, with a luge sole to prevent you from slipping, so you don’t have to stress if the weather suddenly take a turn for the worse. As one reviewer writes, “These are super comfortable and I love the height. Perfect for slushy winter weather. My only criticism is that they are hard to get on and off.” Indeed, they pull on and off, so may feel a little stiff at first. These booties also come in a gorgeous chocolate brown and a “pine needle” green hue.
4. Crown Vintage Tipryn Chelsea Boots
Best Under $100
These $70 boots have a 4.8-star rating and almost 250 reviews, none of which go below 3 stars, which is pretty wild in our opinion. So what makes them so great? For starters, they’re supremely comfortable. Reviewers mention walking in them for miles on city tours or standing in the bleachers for weekend football games in total comfort. They’re also surprisingly lightweight, so they won’t tire your feet with a super chunky sole. They do run true to size, but you’ll definitely want to wear high socks with these (especially while breaking them in) to avoid any chafing, so be sure to consider that when choosing what size to order.
5. Frances Valentine Gem Boots
Frances Valentine is all about crafting gorgeous, long-lasting pieces that you can invest in once and live in for years and years to come. The Gem Boots knock that goal out of the park with a super-chic, classic Chelsea silhouette handmade from Italian leather. A slight heel gives them a posh edge without actually putting any pressure on your feet or ankles, and the toe has an almond shape (not too round, not too pointy) that won’t go out of style any time soon. According to reviews these boots run mostly true to size, but are a bit narrow, so those with wide feet may want to go up a half or whole size.
6. Blundstone 510 Chelsea Boots
These ankle boots by Blundstone are chic enough to wear to work or out to dinner, but are designed to be super-durable and weatherproof, making them a great option for outdoor adventures and inclement weather, too. They come in a whole range of colors as well, if classic black isn’t your style. They offer a ton of support and are “virtually indestructible” per multiple reviews. So while they don’t come cheap, they are built to last for years and years, making them well worth the investment, in our opinion.
7. Marc Fisher LTD. Padmia Chelsea Boots
Many of the boots on this list are comfortable enough to wear day in and day out, but this Marc Fisher LTD. pair combines supreme comfort with a pretty affordable price tag, making it our top pick for this category. A supportive, flexible lug sole cushions your feet while also offering enough bounce to make walking as comfortable as possible. Per one review, “Bought these recently and, after having worn them for an 8-hour day with lots of walking around, I couldn't love them more. They’re incredibly comfortable and I got loads of compliments on the off-white color. I scuffed them early in the day but they cleaned up easily. Couldn't be happier, so I bought them in black too!” Indeed, some do mention that the material scuffs fairly easily, but as long as you address it in a timely manner they should be simple to fix and your boots will continue to look fresh and new for a long time.
8. ASOS Wide-Fit Appreciate Chelsea Boots
Best for Wide Feet
This classic Chelsea boot was specifically designed for those with wide feet, and has extra room throughout so you don’t have to worry about pinching or rubbing in the toe, heel or anywhere in between. And despite the inexpensive price tag, ASOS shoes hold up surprisingly well over time. One downside, however, is that these boots come only in whole sizes, so we’d say opt for the larger over the smaller to ensure your feet are comfortable and have ample room. But on the plus side, they do go all the way down to a size 4—a major win for those with small, wide feet. If you want a wide-fit boot that has a taller shaft, try ASOS’s Alfie boots which are equally comfy and chic as the Appreciate style.
9. L.L.Bean Rugged Wellie Chelsea Boots
Best Rain Boots
Better than other trendy styles like cowboy boots or sock boots, Chelsea boots make for a super chic rain boot. Case in point, this L.L.Bean pair that won’t look out of place even if the weather improves halfway through the day. They’re made from waterproof rubber, with plenty of traction in underneath, and have a slightly smaller opening at the top to prevent water from seeping in there. The insoles are made with EVA pods in the middle and front for extra cushioning, too. Our only gripe is that they come in only whole sizes, so those in between should size up for the best fit.
10. Dr. Martens 2976 Faux-Fur Lined Chelsea Boots
Best for Winter
These Dr. Martens booties are made from slightly thicker leather than other styles and come with a cozy faux-fur lining that combine to keep your feet toasty warm once Jack Frost comes nipping at your toes. They come in both all black and brown with a cream-colored lining (there’s also a black version lined with contrasting white faux fur if you want the lining to pop), but unfortunately are only available in whole sizes. That said, reviewers who typically wear half sizes say going up to the nearest whole size sill fits super well, especially if you factor in a thicker winter sock.
11. Everlane Italian Leather Chelsea Boots
Best White Chelsea Boots
These Everlane booties also come in black and brown, but it’s the combination of the white leather upper, the black gussets and the cream sole that we love most. That lightly colored bottom helps emphasize the bright white above better than traditional black rubber, but won’t show wear as quickly as a matching white would. And the black side panels lend a Mod ‘60s vibe that’s much cooler than monochrome styles. All in all, a perfect little white bootie, and thats before we even get to the buyer reviews. Most folks say they run true to size and lots say they required little to no break-in period (score!). But if you want to wear them with thicker socks in winter, you might want to go up a half size to ensure you have enough room in the toe box.
12. Sam Edelman Laguna Waterproof Pull-on Booties
Best Neutral That Isn’t Black
On the hunt for something that’s a little unexpected but not so far out there as bright red or electric blue? Try this Sam Edelman boot on for size. The “Sesame” leather hue above is neutral enough to go with everything in your closet but will stand apart from the usual sea of black booties, or even bright white styles. They’re even waterproof, so you can break them out on rainy or snowy days without worry, especially with a slightly higher boot shaft that will better prevent water from seeping in the top. As for comfort, one reviewer who works as a hairdresser reports, “I was able to wear these the first day out the box on my feet for 10 hours in complete comfort! Yass!”
13. Nisolo Everyday Chelsea Commuter Boots
Best Minimalist Design
Nisolo’s Everyday bootie really lives up to its name, and is both comfortable and simple enough to wear multiple times a week with tons of different outfits. The side gussets have a triangular shape, rather than the classic rectangle, for a more minimalist vibe, and we adore that the black style is entirely uniform in color (there is, however, a black version with a brown sole if you prefer). The insoles are made from memory foam that conforms to the shape of your foot while still offering support, and the leather uppers have been treated with a weatherproof finish to make them even more versatile. They do run small, so we recommend going up a half or whole size when ordering.
14. Reformation Katerina Lug-sole Chelsea Boots
Best Sustainably-Made Boot
Reformation is one of our favorite places to shop for eco-friendly fashion, and that extends to its shoe line. These boots are made from ethically, sustainably sourced leather and finished with beeswax for weather protection. And the rubber soles are made from recycled materials. While they aren’t exactly cheap, the incredibly classic design is definitely worth the investment, both in terms of style and in the good they do for the environment long-term.
15. Bottega Veneta Tire Chelsea Boots
Trendiest Designer Pick
These Bottega Veneta boots have been spotted on fashion editors, influencers and fashion week attendees time and time again, and we don’t expect the hype to die down any time soon. So what makes them so popular? The unexpected pop of color and the wavy sole add such a special touch to an otherwise classic boot. But on a more practical note, they’re reportedly super comfortable, and the supple Italian leather requires basically no breaking in. The extended rubber sole is water-resistant, but the leather is not, so we highly suggest using a weather-proofing treatment on the upper to better protect your investment.
16. ASOS Raindrop Chunky Chelsea Boots
Best Designer Look for Less
Not looking to drop four digits on a pair of boots right now? This adorable ASOS design has the same trendy touches, but for one tenth the cost. The heel plus the chunky sole adds 3 inches of height overall, but just like the Bottega style, only the rubber bottom is weather-ready, so be sure to apply a treatment to protect the rest of your boot. As for sizing, ASOS currently offers only whole sizes, so if you’re between sizes we suggest going for the larger, especially if you plan to wear thicker socks. Oh, and it also comes in black and pink, for those who prefer a more Barbie-inspired fall wardrobe.
Want to know which buzzy products are *really* worth buying? Sign up for our shopping newsletter to uncover our favorite finds.