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.”