The mods might have made them cool, but it’s Queen Victoria’s shoemaker who’s credited with creating the Chelsea boot. Their aristocratic origins aside, there’s a reason why they’ve become such a classic: The boots are simultaneously utilitarian, streamlined, and sometimes even edgy. If you’ve been searching high and low for a new pair, we turned to shoe-obsessed, stylish women for their favorites.
Best overall | Best less expensive | Best platform | Best less expensive platform | Best chunky | Best small heel | Best less expensive small heel | Best work | Best cowboy-style | Best zipper | Best rain | Best waterproof
What we’re looking for
Size range: You know the drill — we’re on the hunt for footwear that comes in a broad selection of sizes. Here’s where I admit a bit of bias: As someone with slightly wider feet, I always have to go up at least a half size when buying boots. So, for our purposes, there was some preferential treatment given to recommendations offered in half-sizes to accommodate those with wide feet (or just like a little more room for wool socks).
Material: Boots see the worst of the weather — it helps to know what they’re made out of so you understand how they’ll hold up. Your best bet to extend the life of a pair is to waterproof them. This is especially important for leather (which make up the majority of the ones on this list) and suede, as the material makes for “a shoe that’s [like] a sponge,” as Edward Andrade of Cesar’s Shoe Repair explained to Strategist writer Erin Schwartz. A few of these boots are water-resistant or completely waterproof, which we’ve made sure to mention, too.
Design details: The classic Chelsea boot hits just a little above the ankle, dipping slightly at its elastic side panels, and sits on a low-to-almost-nonexistent heel, probably taking a cue from men’s footwear. That precedent has been played with ever since — sky-high shafts and thick platform soles abound now. For every pick on this list, we’ve mentioned features like cap toes, pull tabs on the front and back, and anything else that makes a pair different from another.
Price: Brands at all sorts of price points came up in creating this guide, but, as always, we’ve concentrated on affordability. Each Chelsea boot below is marked as $ (under $200), $$ ($200–$250), or $$$ (over $250).
Best overall Chelsea boots
Sizes 5–11 | Leather | ½-inch platform, slip-resistant lug sole, Docs signature stitching | $
Docs came up more times here than any other boot maker. The 2976s weren’t the pair we heard about the most (see the Floras below), but they take the title here because (a) they fulfill the Chelsea-boot ideal we had in mind in making this list, and (b) they’ve made appearances all over our archives — including our guide to the best ankle boots — as further proof of their power.
London-based journalist Pandora Sykes lives in her oxblood pair, which Docs describes as a more rugged take on its classic Chelseas from the ’70s. That’s what also makes them a favorite of Freddie Harrel, founder of beauty company RadSwan. Harrel likes them more than the Floras for everyday — even though these are more casual, the pair adds an “extra badass edge” to whatever she’s wearing. Jenni Lee, founder of luxury sock label Comme Si, describes them as easy to wear because they have the construction of a functional boot with a silhouette that “looks good even when you’re treading through city slush.” New York Review of Books marketing manager Abigail Dunn shares a similar sentiment, pointing out that they’re a little subtler in a sea of much thicker-soled Docs (but still stand up to heavy abuse). If you do like drama, Elizabeth Tamkin, content and partnerships manager at Kule, pointed us to the Quad version of the 2976s, which have a thick 1.5-inch platform and a 2-inch heel.
Best less expensive Chelsea boots
Sizes 5–11 | Leather | High gloss, 1-inch block heel | $
The Floras aren’t like other Docs, with a glossier finish and without the signature stitching that the boots are known for — which is exactly why our obsessives love them. (They did take the title of the most mentioned pair, after all.) For New York Times senior software engineer Nozlee Samadzadeh, these hit a sweet spot that’s neither too sleek nor too chunky. And the soles do double duty when it comes to practicality and style: The lower-profile heel is no-skid to prevent wintertime slippage and stands out against other (higher) Docs, Samadzadeh explains. Iva Dixit, noted coat collector and the New York Times Magazine editor, agrees that the sole “makes them feel a little more adult.” Dixit has had her pair for years now and says they’re remarkably well-made, looking “like they’ve been worn, but not beaten up,” with the dark sheen developing a patina over time. Hannah Baxter, deputy beauty editor of The Zoe Report, seconds this, saying that because the Floras are British-made, she feels like they’re the “real deal.” If you needed any more convincing, Strategist associate editor Jenna Milliner-Waddell wears hers year-round.
Best platform Chelsea boots
Sizes 35–45 (unisex sizing) | Leather | Metal bumper, cap toe, purple back pull tab | $$$
For a pair of platform Chelsea boots, Scandinavian shoemaker Eytys earned rave reviews from three panelists, including Tamkin and Dixit. It can be difficult to get platforms right — “If they’re too high or too bulky, you look like a tween who just hit up Steve Madden at the suburban mall,” Dixit says — but Eytys doesn’t fall into that trap. The third nomination for the Nikita (one of the brand’s more affordable boots) comes courtesy of Sea of Shoes blogger Jane Aldridge, who says the metal bumper on the toe “sets the tone” for its punk-ish attitude.
Or you can’t go wrong with the Dixit- and Tamkin-approved Ortegas, which are selling out fast. These are too pricey for us to consider them a “best” pick, but if you can splurge, they’re well worth it. They’re not exactly lightweight, but they’re also not “like truck wheels either,” Dixit mentions. Tamkin, too, says the Ortegas are perfect for “clunking around in.”
Best less-expensive platform Chelsea boots
Sizes 6–11 (with half sizes) | Leather | 1.6-inch heel, stacked sole, double pull-loop | $
The Carmels from Free People are a more traditional take than the Nikitas, which might make them a little less edgy but more wearable. Bee Stuart, a personal stylist and founder of QueerYorker, calls them versatile because the shoes are “the perfect ankle length, which complements all jeans and trouser-type pants.” And unlike most of the other Chelsea boots on our list, these come more colors than just black. Stuart favors the olive hue, which reminds her of a classic camo print.
Best chunky Chelsea boots
Sizes 4–11 | Leather | Chunky sole, mid-high shaft | $$
& Other Stories was cited a couple of times by our experts for its high quality at relatively low prices. These Chelsea boots, which are just a little over $200 (making them on the brand’s pricier side), come courtesy of former Strategist writer Hilary Reid, who calls herself an & Other Stories devotee. “The shoes look much more expensive than they are, and I’ve found them to be some of the best quality leather for the price point out there,” she says. These have less of a platform than Eytys’s or Free People’s, but the chunky treaded sole comes in handy on icy sidewalks, Reid says. The boots’ higher-than-average shaft is another reason why they’re our chunky pick.
Best Chelsea boots with a small heel
Sizes 6–11 (with half sizes) | Water-resistant leather | 1.5-inch heel, square toe | $$
Longtime Strategist readers will be no strangers to Blundstones, which are among our favorite work boots for their durability and versatility. But when you want something that’s dressier, enter the Blundstone 63s, which have a low heel for a little more panache than some of the brand’s other offerings. “They really just go with anything and work for everything,” says Strategist newsletter editor Mia Leimkuhler. Emphasis on everything — Leimkuhler once only brought this pair on a weekend trip to Portland that included going to the ballet and a hike up Multnomah Falls. Nadine Abramcyk, co-founder of salon Tenoverten, describes the 63s as both tough enough to “withstand heavy city walking” and feminine at the same time.
Best less-expensive Chelsea boots with a small heel
Sizes 5–11 (with half sizes) | Water-resistant leather | 1.25-inch heel, triangular elastic side panels | $$
These Nisolos are more minimal than the aforementioned Blundstones, which is why they come in second place. But the shoes do feature a barely there block that’s menswear-inspired and more understated than the platformed options we’ve featured here. Peggy Economou, co-founder of nursery clothes brand Teat and Cosset, and Kate McLeod, co-founder of her eponymous label of lotion stones, each have a pair. Economou considers them understated and elegant. McLeod echoes that, calling them a “shoe staple” because they’re easy to dress up and down, along with sliding right on and fitting snugly. To boot, both pointed out Nisolo’s commitment to sustainable practices, operating ethical factories, and fair trade.
Best Chelsea work boots
Sizes 5–11 (with half sizes) | Water-resistant leather | Double pull tabs | $$
There was a time when at least four Strategist staffers owned a pair of Blundstones, which shows in our guide to the best ankle boots, where these 500s make an appearance. These are designed for rough conditions, with a water-resistant finish and high-traction soles. Audio producer Amy Pedulla says Blundstones are big with the podcasting crowd — after years and years of wear, she’s only on her second pair because the boots are designed to last, even as she’s carried around heavy audio equipment from studio to studio. Dancer Eva Alt agrees that they wear really well, especially on slippery walks around the city.
If you’re in need of true safety work shoes, Chicago-based pattern-maker Xochil Herrera Scheer introduced us to the Xena Omegas. The zippered style manages to look stylish and like it belongs on a construction site at the same time. Scheer says they’re extremely wearable, as they are made of flexible leather to make them easier to walk in.
Best cowboy-style Chelsea boots
Sizes 5.5–12 (with half sizes) | Leather | Pointed toe, pitched heel, higher shaft | $$$
When Strategist senior writer Liza Corsillo asked real-life cowgirls and country singers about their tried-and-true cowboy boots, Frye collected the most mentions after Ariat. If you’re a non-traditionalist, the Sachas are a Western take on the classic Chelsea that musician Courtney Marie Andrews calls her absolute favorite — she wears this pair almost every day. This is thanks to their comfort: “Once you wear them in, they form to your foot,” she explains.
Best Chelsea boots with a zipper
Sizes 5.5–11 (with half sizes) | Waterproof leather | 1.5-inch heel, 6-inch height, brass zipper | $
These Ariats are technically paddock boots with a zipper right down the front, but the pull tab in the back and elastic side panels make these qualify as Chelsea boots. Corsillo was convinced to try out the brand after reporting on the aforementioned cowboy boots story. Now, she considers them an old faithful for the winter, especially as the waterproof leather works well in less-than-ideal conditions. The zip makes them easy to take on and off, even more so than traditional Chelseas. Corsillo likes to wear them with cropped jeans as “they cover that weird ankle gap that always gets cold.”
Best Chelsea rain boots
Sizes 5–11 | Waterproof PVC | 1.5-inch heel, 1-inch platform, lugged sole | $
When we asked stylish women from rainy locales (like Seattle) about the rain boots they wear, Jeffrey Campbell came up just as much as Hunter. These are a no muss, no fuss option, as the platform does well against puddles. Style blogger Heidi Grey likes that these are sleeker than thicker rain-boot styles and that once on, they look like a normal Chelsea boot. (They’re also the cheapest boots on our list.)
Best waterproof Chelsea boots
Sizes 6–11 (with half sizes) | Waterproof leather | Double pull tabs, sheepskin footbed | $$
And if you want something that really doesn’t look like a rain boot, consider these Blundstones, which were highly raved about in our guide to the most comfortable shoes, according to pros who stand all day long. Chef Adina Halpern wears the 1477s in and out of the kitchen. These have more support than the ubiquitous clogs and slides, and since they’re waterproof and slip-resistant, they can handle messes — including mud and slush. In fact, Halpern once tested them out on a butcher-shop floor covered in beef fat and didn’t stumble once.
• Nadine Abramcyk, co-founder of salon Tenoverten
• Jane Aldridge, Sea of Shoes blogger
• Eva Alt, dancer
• Courtney Marie Andrews, musician
• Hannah Baxter, deputy beauty editor of The Zoe Report
• Liza Corsillo, Strategist senior writer
• Iva Dixit, The New York Times Magazine editor
• Abigail Dunn, New York Review Books marketing manager
• Peggy Economou, co-founder of nursery clothes brand Teat and Cosset
• Heidi Grey, style blogger
• Adina Halpern, chef
• Freddie Harrel, founder of beauty company RadSwan
• Jenni Lee, founder of luxury sock label Comme Si
• Mia Leimkuhler, Strategist newsletter editor
• Kate McLeod, co-founder of her eponymous label of lotion stones
• Jenna Milliner-Waddell, Strategist associate editor
• Amy Pedulla, audio producer
• Hilary Reid, former Strategist writer
• Nozlee Samadzadeh, New York Times senior software engineer
• Xochil Herrera Scheer, patternmaker
• Bee Stuart, personal stylist and founder of QueerYorker
• Pandora Sykes, journalist
• Elizabeth Tamkin, content and partnerships manager at Kule
• Bryn Taylor, co-founder and creative director of Ouisa
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