Yahoo News The Best Chelsea Boots for Women, Starting at $29
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…
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: Martens 2676 Platform Chelsea Boots
Best Heeled Chelsea Boots: Naturalizer Mindy Waterproof Booties
Best Under $100: Soludos Greenpoint Chelsea Boots
Most Splurge-Worthy: Frances Valentine Gem Boots
Most Practical: Blundstone 510 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 Statement Design: Sorel Brew Chelsea Boots
Most Comfortable: Madewell Citywalk Leather Chelsea Boots
Best Retro Mod Design: Tory Burch Equestrian Link Chelsea Boots
Best Sustainable Boots: Reformation Katerina Lug-Sole Chelsea Boots
Trendiest Designer Pick: Ganni Leather Mid Chelsea Boots
Best for Wide Feet: RAID Radar Chunky Chealsea Boots
Best Rain Boots: L.Bean Rugged Wellie Chelsea Boots
Best for Winter: Martens 2976 Faux-Fur Lined Chelsea Boots
RELATED: The 10 Most Comfortable Boots That Won’t Leave You With Blisters After Just One Wear
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. 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
Best Platform
For those looking for a little height boost that won’t stress your feet, opt for this Dr. Martens platform boot (that 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. The only downside is that these boots come in only whole sizes, and 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. It also comes in a gorgeous chocolate brown and a “pine needle” green hue.
4. Soludos Greenpoint Chelsea Boots
Best Under $100
We were already huge fans of Soludos’ super-comfy sneakers and sandals, but its boots are absolutely worth checking out as well. The Greenpoint booties look far more expensive than their $78 price tag and are made from real leather (or brown suede), so they’ll age beautifully over time. There’s also a cloud-like cushy footbed that will keep your feet happy all day long, even after hours of walking.
5. Frances Valentine Gem Boots
Most Splurge-Worthy
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.
6. Blundstone 510 Chelsea Boots
Most Practical
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. As for support, multiple reviewers rave about how comfortable these boots are, even for those with bunions or plantar fasciitis.
7. 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.
8. 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 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.
9. 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.
10. Sorel Brex Chelsea Booties
Best Statement Design
For those who’d rather stand out from the pack, this Sorel bootie has a very cool exaggerated lug sole and a small pop of neon with the tab in the back that transform the classic Chelsea into something much more fashion forward. And because these boots are Sorel, you know they’re fully weatherproof, incredibly comfortable and durable. P.S. For those looking for something even more outside the box, check out the black-and-red version of the Brex that’s sure to make a statement.
11. Madewell Citywalk Leather Chelsea Boots
Most Comfortable
Many of the boots on this list are comfortable enough to wear day in and day out, but this Madewell pair was specifically designed for city walking, so you know it’s worth the investment. The brand’s proprietary MWL Cloudlift insoles make it feel like you’re walking on—what else—clouds, and the lug sole is both supportive and provides traction for potentially slippery surfaces. And the durable leather upper will only get better with age. Reviews suggest they may run a hair small, so if you’re between sizes or want to wear thicker socks we suggest going a half-size up.
12. Tory Burch Equestrian Link Chelsea Boots
Best Retro Mod Design
The practically flat sole, pointed toe and colorblock effect created by mixing leather, suede and elastic all combine to give these modern boots a decidedly ‘60s vibe. We love that they’re not too literal, but still feel like a cool vintage find that will look fantastic with both Mod shift dresses and raw-hem ‘90s jeans.
13. Reformation Katerina Lug-Sole Chelsea Boots
Best Sustainable 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, too. And 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.
14. Ganni Leather Mid Chelsea Boots
Trendiest Designer Pick
These Ganni 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 in the near future. Much like the Reformation boots above, this Ganni style is made using sustainable materials and production methods. And because of its continued success, the brand has put out multiple color options, including white, baby blue and black with contrasting yellow stitching. What makes them so popular? First off, they look incredibly cool (we love that cap toe and super-chunky sole), but more importantly, they’re very comfortable and are water-resistant too. A true triple threat.
15. RAID Radar Chunky 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 their inexpensive price tag, RAID shoes hold up surprisingly well over time. Oddly enough, these boots come only in half sizes, but if you’re unsure we’d say opt for the larger over the smaller to ensure your feet are comfortable and have enough room.
16. 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.
17. 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.
RELATED: The 19 Most Comfortable Sneakers Money Can Buy, No Matter Your Budget
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