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Nov 02, 2024

13 Best Chelsea Boots 2024 | The Strategist

The Strategist’s carefully chosen and rigorously vetted flagship shopping guides. Learn about our methodology here, and find all our Best in Class guides here. The Strategist’s carefully chosen and

The Strategist’s carefully chosen and rigorously vetted flagship shopping guides. Learn about our methodology here, and find all our Best in Class guides here.

The Strategist’s carefully chosen and rigorously vetted flagship shopping guides. Learn about our methodology here, and find all our Best in Class guides here.

Chelsea boots are utilitarian, streamlined, and sometimes even edgy. But above all, they are easy to wear, with elastic sides that slip right on. Invented by Queen Victoria’s shoemaker, the style has been riffed on for decades by standard-bearers like Dr. Martens and Blundstone as well as newer brands such as Ganni and Vagabond. So in making this guide to the best Chelsea boots for women, I wanted to include all sorts, so I talked to stylish shoe obsessives (including editors, stylists, and brand founders) about the ones they own. Read on for the boots I’ve been breaking in myself, including our best-in-class pick and a few pairs that have been recommended to me over and over. And if you’re looking for more boots, the Strategist has guides to the best women’s winter boots and rain boots as well.

Update on November 1, 2024: Updated prices and checked stock for all products.

I looked for boots that come in a broad selection of sizes, including half-sizes. (As someone with wider feet, I always size up by at least a half-size, a habit I’d also recommend if you like to have more room for thick socks.) I also noted which brands use European sizing and have their own size conversion charts, so you can make sure you’re buying the right size.

The material your boots are made of will affect how durable and weather-resistant they are. Leather is strong. Suede is more high-maintenance, absorbing water like a sponge, so waterproofing is a must (Terrago spray is our best-in-class pick). You can also look for materials that are already water-resistant, like patent leather, or completely waterproof, as some of the pairs here are.

Elastic sides are the feature that makes a Chelsea boot a Chelsea boot. To fit the classic profile, a Chelsea boot should also hit a little above the ankle, come with a pull tab in the back, and have a low heel. However, brands and designers are always reimagining the Chelsea boot, with new details like sky-high shafts, thick platform soles, and even cap toes. I kept an eye out for those kinds of features to build a comprehensive guide with pairs that don’t all look the same.

Based on researching the market and counting all price points that came up while reporting, I marked each Chelsea boot as either $ (under $200), $$ (under $300), or $$$ ($300 and up).

Sizes: 5–11 | Material: Leather | Design: ¾-inch platform, grooving on the elastic gussets, Docs signature stitching, lettering on pull tab | Price: $

Dr. Martens makes functional and durable boots with an edge. The 2976, which has been manufactured since the ’70s, is the brand’s hard-wearing Chelsea boot. The pair is handsome and understated, made from a smooth leather that’s more matte than patent, though there’s some subtle sheen to them. Everyone will know you’re wearing Docs because of the signature yellow stitching — something you’ll either love or hate. But as someone who grew up on the Ramones, I like that the boots feel a little rebellious without drawing too much attention to themselves. I’ve named them the best overall Chelsea boots for their wearability and iconic style. Not only are they sleek, they’re comfortable enough for long days on your feet (my dad used to wear a pair daily while packaging pharmaceuticals on a factory floor).

But getting them there can take time. Docs are infamous for their brutal break-in. New York Review of Books marketing manager Abigail Dunn recommends coating them in the brand’s Wonder Balsam to soften the leather. Another trick to loosen them up is to heat them with a blow-dryer. In the end, I went with the double-sock method, wearing two crews at once, on and off for months, to prevent blisters and rubbing as the shoes stretched out. Because I have bigger calves, the shafts needed the most easing, but now I can slip into the boots painlessly.

I’ve worn mine in both rain and mud, and the boots wiped up easily, even though I haven’t waterproofed them yet. And I’ve heard from people who’ve owned theirs for years, including Comme Si founder Jenni Lee, that they’re very long-lasting — she wears hers while treading through city slush. They get the job done, while adding what RadSwan founder Freddie Harrel praises as an “extra badass edge” — and they come in a platform version too, if you want a more eye-catching look.

Sizes: 6–11 with half sizes | Material: Water-resistant leather | Design: 1½-inch heel, front and back pull tabs, square toe | Price: $$

If the 2976s from Dr. Martens are too utilitarian (or too punk) for your taste, consider the 63s from Blundstone. Blundstones (or Blunnies, as the boots are called in Australia) have a following that includes current and former Strategist staffers, musician Sharon Van Etten and the Princess of Wales. And while the brand is largely known for its rugged round-toe boots, the 63s are billed as a dress boot, with a square toe and softer shape throughout. “They really just go with anything and work for everything,” says former Strategist newsletter editor Mia Leimkuhler. Emphasis on “everything” — Leimkuhler has worn them both to ballet and while hiking up Portland, Oregon’s Multnomah Falls. The 63s are made from water-resistant leather with a durable outsole, and Nadine Abramcyk, co-founder of the salon Tenoverten, describes them as tough enough to “withstand heavy city walking” too.

Sizes: 5–11 with half sizes | Material: Water-resistant leather | Design: 1½-inch heel, front and back pull tabs, double stitching | Price: $$

Though the differences are subtle between the 63s and the 510s, the 510s are more of a typical winter boot, with a rounded toe and more of that signature Blundstone ruggedness. Strategist writer Katherine Gillespie has worn them for the last six winters on the East Coast and says she can’t imagine “conquering the elements without them,” as the lugged sole and “reasonably waterproof” leather mean they can easily handle wet park walks and puddle-filled commutes. (Strategist writer Jeremy Rellosa is also a fan and further “winterizes” his Blundstones with toilet wax.) The boots get a nice patina after a while and don’t require too much breaking in, but they will mold to your feet through wear.

You can’t go wrong with other ankle boot styles in the 500 series, either — each has a water-resistant finish and high-traction soles. Audio producer Amy Pedulla told me that the boots are big with the podcasting crowd, while dancer Eva Alt says they wear really well, especially on slippery strolls around the city.

Sizes: 35–42 (equivalent to sizes 5–11) | Material: Rubber | Design: Logo-print on back, toe caps, grosgrain pull tabs | Price: $$

Fashion content creator Tilly Macalister-Smith originally pointed me to a version of these Chelsea boots from Ganni, the “Danish Mansur Gavriel,” in our guide to the best ankle boots. And Taylor Tomasi Hill, creative and fashion director of the Yes, is another devotee of the brand’s tactical-looking footwear. I liked the edginess of this recycled-rubber style enough to give it a spot on this list. The boots have an indestructible lug sole that, according to Macalister-Smith, has been equally dependable while walking on snowy streets and working in the garden. She especially appreciates that they are made from recycled materials — she usually shops for shoes secondhand and makes it a point to be mindful about a company’s production practices when buying new footwear.

Sizes: 35–42 (equivalent to sizes 5–12) | Material: Leather | Design: 1 ½-inch heel, lugged soles | Price: $

I own three pairs of boots from Swedish shoemaker Vagabond (which also sells excellent loafers) and they’ve all lasted me years (I’ve had my oldest pair for five). These Kenovas come recommended by Strategist deals editor Sam Daly and have a more minimalist look than the chunkier Ganni pair above, with smaller lugs throughout the sole. Daly chose them because the brand is Swedish — and “the Swedes know how to make very classic, non-trendy things.” The boots have become her go-to for everything from going out to swinging by the supermarket. “All my life, I thought comfy shoes meant that they had to be ugly,” Daly says, but the Kenovas are both nice-looking and shoes her podiatrist “would be proud of.” (Pro tip: You can sometimes catch Vagabond styles marked down at Urban Outfitters, which is where I found mine.)

Sizes: 5–11 with half sizes | Material: Water-repellent leather (also available in suede) | Design: Almond-toe, flat sole, higher shaft with gored sides | Price: $

Personal stylist Erica Ball discovered the Cecyls while shopping for a client. From luxury label Vince, which is known for its basics, these boots have a distinctly clean look — their only “embellishment” is a higher-than-usual shaft with an extended gore that wraps around the back for a slightly more dramatic effect. These Chelsea boots caught Ball’s attention for their versatility (she’s a big believer in having a “curated closet”) as she can wear them just as easily with a frillier dress as with a leather jacket and raw-hem denim. Ball adds that these are made of a quality leather and are likely to last a long time, making the Cecyls worth the investment if you subscribe to a “cost-per-wear” philosophy.

Sizes: 5.5–11 with half sizes and wide options | Material: Leather (also available in suede) | Design: Socklike ribbed inset, ¾-inch platform, 2¼-inch heel | Price: $

It can be difficult to get platforms right because, as The New York Times Magazine editor Iva Dixit says, “if they’re too high or too bulky, you look like a tween who just hit up Steve Madden at the suburban mall.” The Hayles, which happen to be from that very company, aren’t that at all. Strategist writer Brenley Goertzen likes the contrast between the ribbed-knit inset where the traditional gusset would be and the combination of the statement-making lug sole with a thicker, flared heel. The nontraditional socklike shaft and stomp-y sole add interest. And the stretchy opening is especially comfortable — Goertzen didn’t even have to break these in. They are one of the most affordable pairs on this list and come in two shades of fairly hardy suede (Goertzen’s even cleaned up well after an unfortunate red-wine spill, despite the fact that she hadn’t weatherproofed them) as well as black or white leather. They are also the only boots on this list that come in wide widths, though many of the wide-width sizes are sold out.

Sizes: 35–41 with half sizes | Material: Suede (also available in leather) | Design: 2¾-inch heel, almond toe | Price: $$$

Even with their block heel, which Chelsea boots don’t usually have, the Rovers (from the usually grungier Rag & Bone) are not ostentatious. The heel blends right in with the rest of the boot, which features vertical stitching on the side panels and a perfectly pointed almond toe. Because the heel isn’t too high, at just under three inches, Portland, Oregon–based wardrobe stylist Grace Thomas found that the boots were comfortable the first time she wore them. Their toned-down appearance was a big selling point: “They will never go out of style,” she praises.

Sizes: 5–11 with half sizes | Material: Water-resistant leather | Design: 1¼-inch heel, triangular side panels | Price: $

These Nisolos feature a barely there blockish heel (available in a contrasting wood tone if you’re so inclined) that’s more subdued than the taller style seen above. Peggy Economou, co-founder of the nursery-clothes brand Teat and Cosset, and Kate McLeod, co-founder of her eponymous label of lotion stones, each recommend the pair. McLeod calls them a “shoe staple” because they’re easy to dress up and down along with sliding right on and fitting snugly. To boot, both pointed out Nisolo’s commitment to sustainable practices, operating ethical factories, and fair trade.

Sizes: 5.5–12 with half sizes | Material: Leather | Design: Pointed toe, pitched heel, higher shaft | Price: $$

When the Strategist asked real-life cowgirls and country singers about their tried-and-true cowboy boots, Frye was one of the most mentioned brands. If you’re a non-traditionalist, the Sachas are a Western take on the classic Chelsea that musician Courtney Marie Andrews calls her absolute favorite — she wears this pair almost every day. This is thanks to their comfort: “Once you wear them in, they form to your foot,” she explains.

Sizes: 5–14 | Material: Waterproof rubber | Design: Double pull tabs, neoprene lining | Price: $

In our best-in-class rain-boots guide, these cheery boots from Merry Peoples — which come in a rainbow of hues including mustard, grasshopper green, and lavender — earned the title of “best Chelsea.” Gillespie was impressed with how city-friendly they are, with a soft and comfortable neoprene lining and a slightly wider fit that’s ideal for wearing thick socks. Two gardeners gushed to us about them too. “They’re just so comfortable and easy to clean,” says Amber Grossman, the creator of Black Girls Gardening. Katie Parks of Freckles and Sprouts adds that the boots “hold up well to our heavy clay soil that clumps to your boots in wet weather, and they have a nice grip, so I never slip.” She gets compliments on her pair all the time.

Sizes: 5–11 | Material: Waterproof PVC | Design: 1½-inch heel, 1-inch platform, lugged sole | Price: $

These rain boots from Jeffrey Campbell are also a good bet, at around half the price of the ones from Merry People (they also have the distinction of being the second-cheapest pair of boots on this list). They are more no-muss, no-fuss — made of a cheaper PVC material rather than rubber — and they only come in black, with a smaller size range. But the platform sole helps guard the top of the boot against puddles, and style blogger Heidi Grey complimented their sleekness, particularly compared to thicker rain-boot styles. Gillespie describes them as “a great option if you like a bit of height and aren’t into the classic Glastonbury-style Wellington look.”

Sizes: 5-11 | Material: Waterproof rubber | Design: 3-inch heel, side zipper, logo on pull tab | Price: $$$

Goertzen bought the Bettys from French fashion house Chloé to replace a worn-out pair of Hasbeens that she’d previously relied on in wet weather. “They perform just like my Hunter rain boots,” Goertzen says. “The rain just beads right off of them. There’s zero water getting into these clompers. So no damp socks.” And because Goertzen lives in Minnesota, known for its long winters, they’ve seen a lot of rainfall, snow, and slush. Since the wellies are made from rubber, a quick wipedown with a washcloth makes them seem brand new, “which is a big deal because here our sidewalks get covered in salt to prevent icy patches,” she adds. And while these are more of an investment, the Bettys are usually marked down during Ssense sales (that’s how Goertzen got hers).

• Nadine Abramcyk, co-founder of salon Tenoverten• Jane Aldridge, Sea of Shoes blogger• Eva Alt, dancer• Courtney Marie Andrews, musician• Erica Ball, personal stylist• Hannah Baxter, deputy beauty editor of The Zoe Report • Liza Corsillo, Strategist senior writer• Sam Daly, Strategist deals editor• Iva Dixit, The New York Times Magazine editor• Abigail Dunn, New York Review Books marketing manager• Peggy Economou, co-founder of nursery clothes brand Teat and Cosset• Lauren Gerrie, a co-founder of catering company Big Little Get Together• Katherine Gillespie, Strategist writer• Brenley Goertzen, Strategist junior writer• Heidi Grey, style blogger• Amber Grossman, creator of Black Girls Gardening• Adina Halpern, chef• Freddie Harrel, founder of beauty company RadSwan• Jenni Lee, founder of luxury sock label Comme Si• Mia Leimkuhler, former Strategist newsletter editor• Kate McLeod, co-founder of her eponymous label of lotion stones• Jenna Milliner-Waddell, Strategist associate editor• Katie Parks, a.k.a. Freckles and Sprouts• Amy Pedulla, audio producer• Nozlee Samadzadeh, New York Times senior software engineer• Xochil Herrera Scheer, patternmaker• Pandora Sykes, journalist• Elizabeth Tamkin, content and partnerships manager at Kule

Additional reporting by Lauren Ro and Jenna Milliner-Waddell.

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