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 sartorially inclined people. It’s easy to see why they’re so popular: They’re streamlined, easy to slip on and off, and have been classic since mods made them cool in 1960s Britain. To find the best Chelsea boots out there, 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, 29 foliage-stomping pairs, as recommended by our panel of cool people.
The best classic Chelsea boots
This chunky take on the Chelsea was called out as a favorite by two of our panelists, including London journalist and podcaster Pandora Sykes, who says she lives “in a pair of chunky-soled, patent oxblood short Chelsea boots. Next on my list are a white pair.” Freddie Harrel, the blogger turned founder of beauty company RadSwan, also loves the Dr. Martens Chelsea for its thick sole and signature yellow line. “This pair adds an extra badass edge to any outfit,” she says.
For something a little sleeker, consider the Flora, which features polished leather and a monochromatic look. It’s one of Coveteur senior beauty editor Hannah Baxter’s favorite boots (she owns multiple Docs), and because the brand is British, she feels like they’re the “real deal” Chelsea boots.
Two 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 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 comfort, 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.
Eva Lee, content operations manager at Refinery29, loves these flat Chelsea boots for their versatility. “You can wear them with anything: cropped jeans, trousers, or with tights under a skirt,” she says. She cites the shape of the toe and the shaft height as making them “the perfect middle ground between casual but still feminine.”
Everlane’s Chelsea boot is classic all the way, too, with a leather heel tab, squared elastic panels for easy on-and-off, and a toe that’s pointed just so. It comes recommended by publicist Sonya Li Casino, who loves the tapered toe and simple silhouette.
Jane Aldridge of the blog Sea of Shoes recommends these Chelsea boots by Daryl K. “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.”
Here’s a daintier glossy boot with a pointed toe, recommended by Maisonette’s other co-founder, Luisana Mendoza de Roccia. She calls the classic style “both elegant and functional.” And the tiny Prada logo embossed in white is a just-subtle-enough way to flex your taste.
A few of our cool women say the best Chelsea boots aren’t only found in the women’s shoe section. Brooklyn-based fashion blogger and stylist Allison Graham, who shows off her European menswear-inspired style on her blog She Does Him, told us she likes these men’s Chelsea boots by Saint Laurent in a tan suede. “I’ve always been a huge fan of Saint Laurent’s Chelsea boots, as I’m very big on quality and colors.” Baxter agrees, saying that although the Wyatt boots are for men, “There’s no reason why you can’t snag your size and look just as cool as the boys.” She calls them “the quintessential rock-and-roll Chelsea boot,” and we don’t disagree.
Best Chelsea boots with a lift
Platform Chelsea boots seem to be the trend to try this fall, and these from Dr. Martens — arguably the favorite brand among our experts for always cool, never-go-wrong Chelseas — are one of your best bets this season. Man Repeller’s market and affiliate strategist Elizabeth Tamkin already owns a pair of patent leather Docs, but told us she’s hoping to upgrade to this elevated pair for the many wet days ahead.
For something with a little more lift than the Daryl K boots, Aldridge recommends Eytys’ chunkier Nikita boots. “I love any boots with monstrous proportions, so these clunky Chelsea boots caught my eye immediately.” While her favorite pair in crocodile-effect leather is sold out, the Nikitas are still available in black leather. Tamkin also recommends a clunky pair from Eytys, the slightly more streamlined Ortega boot, which also provides a pretty hefty lift, courtesy of a two-inch heel.
Best brogue-style Chelsea boots
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.
Tamkin also told us she looks to the boys for her Chelsea boots. “I love men’s footwear,” she says. “Something about the toe, the details, and the width is always more pleasing to me.” Her favorite is a brogue-style pair from British heritage brand Grenson, which started with men’s boots and has since released this version for women. Tamkin calls them “the most perfect brogue Chelsea boot” and imagines that they would look smart worn “with a wool suit or perhaps a perfect plaid trouser.”