As the air gets nippy and the leaves start to change, one of the things we look forward to most is the chance to don our autumnal best. For many of us, that means pulling on a pair of tried-and-true Chelsea boots, a staple shoe in the wardrobes of countless well-dressed people. It’s easy to see why they’re so popular: The boots, which are typically characterized by their ankle height and elastic side panels, are streamlined, easy to slip on and off, and have been a classic since mods made them cool in 1960s Britain (though they were around long before that). To find the best Chelsea boots, we asked stylists, fashion bloggers, and all-around stylish women for their favorites, from sleek classic leather ones to chunky platforms and everything in between. Below, 21 foliage-stomping pairs, as recommended by our panel of cool people.
Best classic Chelsea boots
Dr. Martens Flora boots came up more than any other Chelsea boots mentioned by our experts. For software engineer and self-proclaimed “sewist” Nozlee Samadzadeh, the Flora boots hit a sweet spot: “I scoured stores for a Chelsea boot that isn’t too sleek but isn’t too chunky, and I am so happy with these,” she says. The monochromatic boots are made from polished leather and have a lower-profile heel and opaque sole that Samadzadeh says make them different from other Docs (which typically have a chunkier, brown heel). The fact that the soles are no-skid makes these perfect for winter, too, Samadzadeh adds. Iva Dixit, a noted coat collector and an editor at the New York Times Magazine, also owns Floras (in burgundy) and agrees that the rubber sole — which lacks the British shoemaker’s signature yellow stitching — “makes them feel a little more adult.” She adds that these “are an incredibly well-made shoe for the price.” Dixit has had her pair for three years, saying they now “look like they’ve been worn, but not beaten up,” and that “the dark sheen patinas beautifully over time.” The Floras are also among the favorite Chelsea boots of Coveteur senior beauty editor Hannah Baxter, who says that because their maker is British, she feels like they’re the “real deal.”
This chunkier take on the Chelsea by Dr. Martens’s came in a close second; it was named a favorite by two of our panelists, including London-based journalist and podcaster Pandora Sykes, who says she lives in her (oxblood) a pair of the chunky-soled, patent leather boots. Freddie Harrel, the blogger turned founder of beauty company RadSwan, also loves the Dr. Martens 2976 Chelsea for its thick sole and signature yellow stitching, which make these a bit more casual than the Floras. “This pair adds an extra badass edge to any outfit,” she says.
Two more of our stylish women, Teat and Cosset’s Peggy Economou and Kate McLeod, a co-founder of her eponymous brand that makes all-natural lotion “stones,” recommend these everyday Chelsea boots from sustainable shoe company Nisolo. Economou loves that they’re “understated and elegant,” and McLeod says they’re “quickly becoming my new shoe staple” because “they can be dressed up or down, slide right on, and fit snugly.” Both women add that they appreciate Nisolo’s commitment to quality, ethical factories, and fair trade. “Nisolo partners with Ecosphere to offset carbon emissions and ensures that their artisans have proper health care and are earning fair wages,” explains McLeod.
Blundstone’s classic boots are a Strategist favorite for their durability and versatility — especially for snowy weather. But sometimes you want to wear something that’s not as utilitarian. Enter Blundstone’s Dress Chelsea Boots, which have the same look and reliability of its classic work boots, but are just a little, well, dressier. “They really just go with anything and work for everything,” says Strategist newsletter editor Mia Leimkuhler. “I once took them as the only pair of shoes on a weekend trip to Portland that included both going to the ballet and on a hike up Multnomah Falls, and they were great for both.” Nadine Abramcyk, a co-founder of salon Tenoverten, also prefers this style (but in a different finish) over the Australian brand’s popular work boot. “They’re utilitarian and can withstand heavy city walking while still looking feminine,” she says. The water-resistant boots have a chiseled, square toe, a more streamlined profile, and a thinner, slip-resistant sole.
Eva Lee, the head of newsroom operations at BuzzFeed, loves these low-heeled Chelsea boots from Madewell for their versatility. “You can wear them with anything: cropped jeans, trousers, or with tights under a skirt,” she says. She says the shape of the toe and the shaft height make them “the perfect middle ground between casual but still feminine.” The leather boots have covered elastic side panels that make them look a little sleeker, padded insoles, and are also available in a brown color called “English saddle.”
Sea of Shoes blogger Jane Aldridge (who knows a lot about footwear) recommends these Chelsea boots by Daryl K. With their covered elastic panels and similarly shaped toe, you could call them the sophisticated big sister to the Madewell pair above. “I always wear them a lot this time of year,” she says. “They’re about as classic as it gets, and I always get compliments on them when I wear them.” Aldridge adds that they make “great travel boots, too.”
Celebrity stylist Tara Swennen, who is best known for dressing Kristen Stewart, recommends Frye’s Melissa boot because it looks good and, importantly, holds up. “This is a staple boot that’s not only durable but also super-sleek,” she explains. Made of polished Italian leather, they have an added bit of embellishment in the form of a button on the back pull tabs.
These Chelsea boots from Rachel Comey come recommended by fashion illustrator Annie Reeds, who likes how they’re “narrower, dressier, and secretly weatherproof due to the patent leather.” Perhaps because it’s been months since most people dressed up, she “really appreciates a more formal shoe” like this right now, adding that “a shoe and a coat are the easiest way to trick an outfit into smartening up.” When going to the grocery store is “the only form of Being Seen,” Reeds says having “a slightly more pulled-together everyday boot” like the “low-heeled but slick Thora” will ensure you get noticed.
With their dainty toes, narrow body, and lower heels, these Chelsea boots look a lot like the Rachel Comey ones above — but they cost a fraction of the price. They come recommended by mom of two and fashion buyer Grace Lim, who calls them a great affordable option. She says the squared toe gives the boots a “polished and sleek” look, adding that they pair well with “a distressed skinny ankle jean and a fitted turtleneck.” And even though they’re less expensive, these are still made of leather.
Best Chelsea boots with a lift
For chunkier, almost oversize Chelsea boots, three of our cool women say you can’t go wrong with a pair from Eytys. “I love platforms,” says Dixit, who owns the Ortegas in a brown snake-embossed leather. But she warns that, with any platform Chelseas, you are (literally) walking a fine line: “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 the Ortegas are “hefty but still elegant,” noting their thick sole is made of crepe and cork. While they’re not exactly lightweight, they’re also not “like truck wheels either,” according to her. Elizabeth Tamkin, a market editor at Repeller, also likes the Ortegas (in black), agreeing that they are great for, as she puts it, “clunking around in.” She adds that, with them on, you’ll have “warm feet and be two-inches taller.” Aldridge, meanwhile, is a fan of Eytys’s less expensive Nikita boots, saying, “I love any boots with monstrous proportions, so these clunky Chelsea boots caught my eye immediately.” The Nikitas, she adds, have a metal bumper on the toe that “sets the tone.”
If you’re looking for an even less expensive way to dip your toes into the world of platform Chelsea boots, these from Dr. Martens — arguably the favorite brand among our experts for always cool, never-go-wrong Chelseas — are one of your best bets. Tamkin told us about them, saying that she already owns some patent leather Docs but is hoping to upgrade to this elevated pair for the many wet days ahead. They’re basically identical to the classic 2976 Docs near the top of the list, but have a thick 1.5-inch platform and a 2-inch heel.
“I love No. 6 shoes, but I am NOT a clog person,” says Reeds of the brand synonymous with the clogs worn by a certain subset of cool women. “But the rest of their stuff uses quality materials, in shapes that are interesting enough, but stay relevant in subsequent years.” That’s why she likes these “clunkier workhorse pull-on boots” with a thicker sole and heel, noting that they’re “good for clomping around in a wintry mix.”
If you want a Chelsea boot with a an even chunkier heel, art director Madelynn Furlong recommends this style from British heritage brand Church’s that has a glossy finish and a slightly pointed toe. In recommending them, Furlong told us that Céline once made the platonic ideal of the Chelsea boot — and these are the closest dupe she’s found for the now-discontinued Céline pair that she loves.
Best statement Chelsea boots
For those who want an even more unique pair of Chelseas, our cool women told us about some white and embellished styles that command even more attention. Dixit owns these Labucq Chelsea boots in white; they have a rugged Vibram sole, making them great for wintry weather. “I have very wide feet and very high arches, so I like a chunky boot that I can stomp on gross, wet, icy pavement with,” she says. While they’ll inevitably get dirty because of their color, she says they’re very easy to wipe clean. Tamkin is a fan of Labucq’s Suba boots, too (she likes them in black). Like Furlong, Tamkin says these remind her of old Céline, noting that their chunky sole makes the boots “perfect for wet slippery leaves.”
For a twist on the traditionally unadorned Chelsea boots, London-based fashion stylist and blogger Alex Stedman suggests these British-made, brogue-style Chelsea boots that she’s had “for years” and calls her “all-time favorites.” She adds that “they’re such a classic pair, and they’ll definitely come into their own again” now that fall has returned. Made in Italy, they’re also available in tan.
For a Chelsea boot with some preppy flair, might we suggest Stuart Weitzman’s take, which comes recommended by Liza Bychkov-Suloti, an on-air style expert and partner at integrated marketing and PR agency SHADOW. When choosing a Chelsea boot, she looks for a pair that has a narrow toe and an “edgy heel.” Bychkov-Suloti adds that she loves the faux-pearl trim on these, which give them a feminine touch.
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