The 12 Very Best Chelsea Boots for Women

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: 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: 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.