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.