The 13 Very Best Ankle Boots for Women

Sizes: 37–42 | Material: Leather upper (that’s water-resistant), rubber (Vibram) sole | Design details: Zipper front, shearling lining, 3” heel | Price: $$

Maguire’s water-resistant Estrellas have soles made with Vibram — a trademarked rubber used in many a Blundstone and Merrell, so they can handle some inclement weather. “These are great when it’s very cold outside, even with a little snow on the ground,” says Elizabeth Cardinal Tamkin, author of the newsletter The Corner Booth, who’s worn these for two winters. She says the zipper is “super helpful if you have on a thick sock — you don’t have to jam your foot into the boot,” she tells me. They’re so comfortable that she’s been wearing them while nursing a broken knee recently. “They didn’t need to be broken in, and they’re very easy to take off,” she says.

Sizes: 35–41 (equivalent to US sizes 4 to 10.5) | Material: Leather upper and sole | Design details: 2.25” block heel, square toe | Price: $$

The Lazaros are LoQ’s signature block-heeled boot with a square toe and zippered sides. They’re an investment at $395, but they’re well constructed — made in Spain from a supple leather that can take the occasional scrape without scratching easily. These have some texture to them with crinkled leather in the front that’s not as smooth as the leather on the Docs above; it’s a small contrast but one that I thought gave the boot a little edge. The heel, which extends a bit off the back of the boot (see here), adds to that feeling. The boots are practical for their two-and-a-half-inch block heel. I can stand for longer stretches and walk for blocks of uneven sidewalks without issue. Since trying them on for the first time in July, the boots haven’t been as challenging to break in as stiffer boots like Docs, even as someone with wider calves. But Strategist writer Lauren Ro found that the opening at the ankle is tight at first, even when buying them in her usual size 38 (she found that it stretches after a few wears, and Ouisa founder Bryn Taylor promises that, eventually, the boots will become almost slipperlike). I think what helped my pair break in faster was sizing up, per LoQ’s own instructions — I’m usually a seven and went with a 39, which is an eight/eight and a half in the brand’s European sizing. 

[Editor’s note: These boots are currently sold out in most sizes, though you can sign up to receive an email when your size is back in stock.]

Sizes: 5–11 (half sizes available) | Material: Leather upper and sole | Design details: 2” block heel, almond toe | Price: $$

Everlane’s shoes have often been compared to gloves, and these are no exception. (You might remember Everlane selling an earlier version of the boot under the same name. It has since been redesigned with a taller shaft than the original’s — which one of the Strategist’s resident Everlane experts had owned — with more of a curved silhouette on the side.) When I tried a pair, they were easy to pull on and there was enough room for my toes to wiggle without rubbing against the lining. They are also more than $100 cheaper than the Lazaros, and the differences between the boots are slight. The heel on Everlane’s boots is just about half an inch shorter than the heel on the LoQ boots, and while it’s not as blocked in terms of thickness, it’s comfortable enough that I never felt like I might stumble. Even though the Days are branded as having a square toe, they have more of a rounded, not-so-narrow almond toe compared to the Lazaros, resulting in a roomier toe box. The biggest difference comes down to the leather — I’ve noticed a few creases along the front stitching of the Days since getting them in October. The lines aren’t so noticeable, but I’ll be keeping an eye on them to see if they worsen with more wear.

Sizes: 35–41 | Material: Leather (calf) upper and sole | Design: 3” heel, pointed square-toe | Price: $$$

Berlin-based accessories house Aeyde was popular with our panel — Taylor, Sokolov, and Sold Out NYC founder Kiane von Mueffling mentioned it. All three like how Aedye’s pointed toe is ever so slightly squared at the end, giving its shoes a subtle western vibe. Sokolov and von Mueffling specifically directed us to the Leandras. A self-proclaimed Aeyde obsessive, von Mueffling praises the style’s high-quality leather, which is priced fairly and wears well over time, while Sokolov likes how the boots’ glossy finish dresses up the most casual of outfits.

Sizes: 35–43 | Material: Leather upper, wood base with polyurethane sole | Design details: Shearling lining, 2.5” heel, 1” platform | Price: $$

As we’ve written before, No. 6 clogs are a favorite of artsy moms from Boerum Hill to Silver Lake, and they’re worn by everyone from Julianne Moore to Michelle Williams. But unless you’re in the clogerati, you might’ve missed that No. 6 makes clog boots that are around the same price range as Swedish Hasbeen’s. If you wait long enough (and stock willing), you can even get them during the store’s annual sample sale — as writer Alexis Cheung did, getting her first pair in 2016 and a second in 2023. “They might get a little scuffed, but you can wear them for years before needing a new pair,” Cheung says. “They’re great for winter because you don’t need to wear socks with them, your feet stay incredibly warm, and they can handle snowy days.” And while these sit on a 2.5-inch heel and one-inch platform, it’s a comfortable height — mostly. “The heel is a bit tippy,” she warns. “I always grab a stair railing for fear of falling. But other than that, I find them easy to walk in.”

Sizes: 5-11 with half sizes  | Material: Polyester, nylon, and elastane upper with a leather sole | Design details: Ribbed detail, 2” heel  | Price: $

The Glove Boot comes recommended by both Christel Langué and blogger-TikToker Nana Castro. “These are made from renewed plastic bottles, though you’d never know from the knit look,” says Castro, as the ribbing is especially convincing. They have a just-right stretchiness, while still feeling supportive. Langué turns to them whenever she has a full day of walking ahead — with the pedestrian-friendly heel, they keep her as pain free as possible. Plus they are one of the cheapest pairs of boots on this list.

Sizes: 5–12 | Material: “Stretch material” shaft, leather upper, rubber sole | Design details: Pull tab, treaded outsole | Price: $$$

It feels like you can’t walk a few blocks in Greenpoint (when it’s winter, at least) without seeing someone in what appears to be the Barla Boot from Rachel Comey. (I’m almost certain I spotted artist Edith Young in a pair on Instagram not too long ago.) Brand consultant Nancy Rosenbloom told me that her Barla Boots have survived frequent treks through New York City and have been regularly in her shoe rotation for over six years. Now, she lives in Vermont, where the boots stand up to much more inclement weather. “They seem to be completely waterproof in rain and slush,” she tells me. Because of the rugged, lugged sole, they have plenty of traction, too, and they’re easy to slip into, thanks to the shaft, which is made from a stretch material (Rosenbloom describes it as a neoprene) and a pull tab that “slides [them] off, like a Blundstone.” Just note that the boots can run a half-size small. The glossy spazzolato might feel a little stiff, while the nubuck-like brushed-off finish has a bit more give from the beginning.