A version of this story originally appeared on the Strategist U.S.
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 see the appeal of the Chelsea boot, especially at this time of year. Not only do they pair with almost any outfit, but they can brave whatever weather conditions are thrown at us as winter approaches.
To find the best Chelsea boots to suit anyone’s style, we asked stylists, fashion bloggers, and all-around stylish women for their favourites, from sleek leather ones to chunky platforms and everything in between. Below, 17 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 favourite by two of our panelists, including 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.
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.”
Strategist UK editor Ailbhe Malone favours a different Australian boot. “I first spied R.M Williams boots when I was in Tasmania, and then again in Melbourne”, she says. “They’re expensive, but they’re the Australian version of a Church’s loafer — they last for a million years, and can be worn with a suit (I’ve worn mine to weddings), or with a miniskirt.” Malone recommends trying the boots on in-store, as they run a little narrow, but also mentions that after purchasing, if you’re ever near a R.M Williams store, you can drop in and get a free clean and polish while you wait.
“Tod’s Leather Chelsea boot is the everything boot”, says Maisonette co-founder Sylvana Ward-Durrett. She says it works equally well with jeans or with tights and a dress. We like the low heel on this guy and the elastic side panel that’s shaped like a T.
[Editor’s note: Unfortunately, Sylvana’s exact pick is out of stock, but we spotted this similar pair, also from Tod’s, available to shop now.]
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.
[Editor’s note: Whilst Luisana’s boots are no longer available, we spotted this remarkably similar pair, also from Prada.]
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 colours.” 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
Personal stylist Bee Stuart told our sister site about these chunky Chelsea boots from COS. “Most Chelsea boots stop right at the ankle, but these go two to three inches above the ankle, which really makes them unique and super-stylish,” she says. The boots have a stretchy elastic panel, meaning they won’t pinch your calves once they’re pulled on. They also have a rubber lug sole, which Stuart says gives them an “edgy ‘cool’ factor while still remaining very timelessly chic.” For Stuart, part of the boots’ appeal is their ability to be worn with jeans tucked into or hanging over the slightly raised shaft. But when she’s not in jeans, her favourite pair of bottoms to style them with are some leather trousers. “They look so sexy and badass,” she says.
Platform Chelsea boots seem to be the trend to try this autumn, and these from Dr. Martens — arguably the favourite 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.
Illustrator and designer Poppy Almond favours these high, chunky Chelsea boots from Ganni. “I love stomping around the city in them,” she says. “They give me so much confidence.” She says the boots, in which she opted for in a half-size up to fit thick socks, offer a comfortable amount of room around the calves and legs. Almond also says that she thinks the boots are worth the slightly higher price as, not only will she wear them for many winters, she can style them for evenings out with big dresses, and casually under her jeans through winter. She does warn, however, to keep some plasters at the ready for their first few outings. “My feet are currently covered in blisters,” she says. “However, the first time I wore them, I ended up doing 30,000 around London Fashion Week – so they maybe just needed to be broken in first!”
[Editor’s note: Poppy received the boots as a press sample, but has no commercial partnership with the brand.]
Best brogue-style Chelsea boots
For a twist on the traditionally unadorned Chelsea boots, 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 favourites.” She adds that “they’re such a classic pair, and they’ll definitely come into their own again” now that autumn 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 favourite 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.”
Best statement Chelsea boots
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.
Best old Celine–style Chelsea boots
According to Tamkin, past season Celine Chelsea boots are the platonic ideal of the style. But if you can’t find any on Vestiare Collective, she says these from Labucq will do. She loves the chunky tread sole of this particular pair, and recommends offsetting the bulk with “a girly tea-length dress.” [Editor’s note: This price does not include shipping fees.]
Best white Chelsea boots
Photographer and graphic designer Shini Park of Park and Cube likes these square-toed socklike boots from By Far: “These ankle boots are the perfect winter whites.” When we asked her how she wears them, she told us to “pair with classic jeans or with a skirt,” and that they have a “great heel height for stomping around, too.”
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