I Spent This Winter Trying Out Ankle Boots — and the Best Are Under $200

What we’re looking for

Sizes: 5-13 (with half sizes 5.5-9.5) | Material: Leather upper, elastic part of the shaft, synthetic outsole | Design: Side zipper and panel, 1.75” heel | Price: $

Franco Sarto isn’t a name that came up while reporting out this guide originally — but in my experience, you can’t go wrong with the brand. (Its Lyanna slingbacks are a runner-up in our hunt for starter heels and the Bocca is a longtime recommendation in our guide to loafers.) This is especially true for its boots. They’re reasonably priced — nearly every style of boot Franco Sarto currently sells is under $200 — and good quality (meaning they can be worn over more than a single winter). I’ve been trying the Luella, Saydie, and Gracely styles over the past several months, and while the Luellas and Saydies are favorites, the Gracelys are my favorite-favorite.

Before I tell you more about them, I’ll say that I’d rather be wearing anything other than a boot. (I’m the writer behind our list of winter shoes that aren’t boots.) Still, I wore Gracelys every day I could this winter — they’re that good. For one, they’re easy to style, even under layers. I’d credit them with helping me survive this miserable winter, from the below-freezing temperatures in January and the aftermath of a snowstorm in February to just the regular gray days of December. They’ve kept my feet warm, and I love that I don’t have to be precious about them. They’re very forgiving — even after I’ve worn them down countless snow-covered blocks, they don’t look like they’ve been dragged through countless snow-covered blocks. It’s not a struggle to get them on and off thanks to the side zipper. I wore them right out of the box without a single blister (it might’ve helped that I requested a size eight instead of my usual size seven to accommodate socks). I can’t ask for more from a boot that retails for $175.

Sizes: 6-16 (with half sizes 6.5-13.5) | Material: Leather upper (water-resistant), elastic part of the shaft, TPU outsole | Design: Extra set of footbeds, stitching around heel and gusset, dual pull tabs | Price: $$$

It feels like you can’t walk a few blocks in Greenpoint without seeing someone wearing the Barla Boot from Rachel Comey . They fare well in other cold parts, too. Noihsaf Bazaar’s Kate Lindello told me she relies on her Barlas extensively living in Duluth, Minnesota, “where anything above 30 degrees is considered balmy.” They’ve also been in brand consultant Nancy Rosenbloom’s rotation for more than six years: first for trekking around New York City and now for Vermont, where she currently lives. “They seem to be completely waterproof in rain and slush,” Rosenbloom says. Thanks to their rugged lug soles, they have plenty of traction. And they’re easy to slip on, with the shaft covered in a stretch material (Rosenbloom describes it as similar to neoprene) and a pull tab that “slides them off like a Blundstone.” The glossy spazzolato might feel a little stiff, while the nubucklike finish has a bit more give from the beginning. (The brand recommends sizing up at least half a size in every Barla style.)

Sizes: 5-12 | Material: Leather upper (water-resistant), Tencel lining, rubber outsole | Design: Western-style stitching, pointed toe, pull tabs, 1.5” heel | Price: $

I have had pairs of Vagabond boots longer than my time working at the Strategist, and this will be my fifth year as a writer here. So while this is one of the cheapest pairs on this list, you’re getting more than your money’s worth in terms of quality and longevitiy. I heard about the Kelsey from author Eliza Dumais. As she says, there’s a “Western grandeur” about the Chelsea style (without being entirely cowboy-y) in no small part because of the pointed toe, a shaft that’s high enough to reach the hem of anything cropped, and a low heel. They’ve “faithfully carried” her across the Nightmoves dance floor, a walk to the A train when the G stops running on weekends, and even vineyards and caves in the Loire Valley, which was an “all-terrain experience of soil, cobblestones, mud, gravel.” Note that they definitely run on the narrower side and that “when they’re new, the point does squeeze your toes.” Still, “they break in super nicely and they really do hold up over time,” Dumais says. After she originally got them in 2018, she replaced them with an exact-same pair in 2023.

Editor’s note: Vagabond will occasionally “discontinue” a style, only for it to come back another season under the same name but with a slight change, like a higher shaft — in the case of the Kenova that appear in another Best in Class guide — we’ve linked to the new version of the Kelsey that’s nearly identical to the style of Kelsey Dumais has.

Sizes: 5-12 | Material: Leather upper, canvas shaft, rubber outsole | Design: Yellow welt stitching, branded pull tab, elasticated gusset | Price: $

Manufactured since the 1970s, the 2976s are Docs’ original Chelsea style, and there’s a certain appeal to the yellow stitching even nearly half a century later. Like Blundstones, Dr. Martens can lean informal. (There’s a version with a high-shine finish named the Flora, if you’re so inclined.) But when I think about the words “Chelsea boots,” I picture a boot that looks like 2976. The 2976s are nothing if not a workhorse of a boot (my dad even used to wear his while working at a pharmaceutical factory). Mine have saved me from puddles and sleet. Other fans:The New York Review of Books’ marketing manager Abigail Dunn, Marie Claire beauty director Hannah Baxter, and Comme Si founder Jenni Lee. But here’s something important to note: Docs are notoriously stiff at the start. I suggest layering on socks until they stretch out a bit. (And “breaking in” is different for everyone, as I learned reading through the Dr. Martens-related sub-Reddit.) That said, they get more comfortable by the day. (Dunn also uses brand’s Wonder Balsam to make them “pretty much indestructible.”)

(Other Docs of note: the 1460, which were introduced in 1960, and have since been worn by the likes of the Clash and the glitterati. Catbird chief creative officer Leigh Plessner likes how they look with nightgowns.)

Sizes: 5-11 (with half sizes 5.5-10.5) | Material: Knitted (water-repellent) upcycled materials, rubber outsoles (anti-slip) Design: More roomy square-toe box, sock-like shaft, pointed toe, pull tabs, 2” block heel | Price: $

Where Zoë Sessums, writer of the newsletter Archive of Everything, lives in Maine “tends toward lots of snow, ice, mud, and walking on trails and rugged sidewalks,” making it hard to wear anything other than Blundstones. That is, until she discovered this water-repellent Vivaia pair. They’ve survived three winters in a row now. “They feel somewhere between a compression and a wool sock,” she says. Sessums even wore them to DJ a friend’s party. “I maneuvered my sloped, gravely, icy driveway, loading and unloading equipment from the car to the venue, and the entire party (grooving and standing) with comfortable feet,” she says. “I was amazed at how I wasn’t thinking about any aches or pains throughout the night or when I finally took them off.” (Vivaias are known for being comfortable: its flats are worn by restaurant people.) The one caveat: Because they’re knitted — similarly to a Rothy’s — they aren’t the warmest. “Sometimes if I start with cold feet, it takes a little while to warm up since there isn’t much wiggle room to get the circulation going.”

Sizes: 36-43 (equivalent to 4-12) | Material: Leather upper (water-resistant), shearling on the inside, rubber (Vibram) outsole | Design: Zipper front,shearling lining, 3” heel | Price: $$$

Maguire’s water-resistant Estrellas are outfitted with Vibram — a trademarked rubber used in many a Blundstone and Merrell. “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. You could say they’re “snow boots that don’t look like straight-up snow boots.” (The coldest temperature she’s worn them in was nine degrees.) And the zipper is “super-helpful if you have on a thick sock — you don’t have to jam your foot into the boot.” This came in handy when she was nursing a broken kneecap last year. “They didn’t need to be broken in, and they’re very easy to take off,” she adds.

Editor’s note: Some sizes are sold out, but you can sign up to receive an email when your size is back in stock.

Sizes: 6-16 (with half sizes 6.5-13.5) | Material: Leather upper (water-resistant), elastic part of the shaft, TPU outsole | Design: Extra set of footbeds, stitching around heel and gusset, dual pull tabs | Price: $$$

This winter, our senior editor Hilary Reid found what she hadn’t been able to find for some time: a good New York winter boot (which she defines as “one that’s not a snow boot but can be worn in the snow and slush, not a going-out boot but can be worn out for dinner and to the office, and not explicitly outdoorsy-looking but that can be worn in the city’s ten-degrees-but-feels-like-minus-11-freezing-cold-pavement great outdoors.”) Diane B. — which has stores on Third and Lexington Avenues — is where they were. “A lot of its styles are strongly reminiscent of more expensive designer styles … at prices that are not low by any means but a lot less than you’d pay for those pairs and, from what I can tell, just as well made,” she explains. Reid’s exact pair isn’t sold online, but the similar Stormytwo is available on the site. They’re made from the same suede, with a very warm shearling lining and a top that “can fold up or down to either show the shearling or give them a slimmer fit through the ankle,” she adds. At $450, Diane B.’s Stormytwo is similarly priced as Maguire’s Estrella, at $390 (both with a zip front) — but you do get the look of two boots for the price of one.

Sizes: 33.5-45 (equivalent to 3.5-14) with medium, narrow, and wide widths available | Material: Leather upper and outsole, foam padding | Design: Size zip, pointed toe, 1.5” heel | Price: $$

It’s because of the reputation Margaux has in our Strategist circle (our former senior editor Kiki Aranita’s slingbacks from the brand don’t retail for a Chanel price but are Chanel-y anyway and Reid’s sandals have traveled to Jamaica and Italy) that I’ll rationalize making the investment of the Ingas from Alex Mill’s collaboration with Margaux. Is $495 a lot to spend? Absolutely. But you’ll be getting something that’s really well-made (there’s a reason why Margaux comes up in different Strategist guides). This winter, Reid has relied on them any time she wanted to look put-together. They’re not “overly trendy,” thanks to the “snip-nose” toe that’s not quite pointed and stiletto-inspired kitten heel (I can’t help thinking of old Prada because of it, actually). Not only are the heels sturdy, they’re “extremely comfortable.” Unlike other styles on this list, the Inga is also available in different widths: medium, narrow, and wide for a better fit. “I know that I will be wearing these for seasons to come,” Reid adds.

Sizes: 35–42 (equivalent to 5-12) | Material: Leather upper, wood base with polyurethane outsole | Design: Shearling lining, side zip, different finishes across colorways, 2.5” heel, 1” platform | Price: $$

As we’ve said before, No. 6 clogs are a favorite of moms from Boerum Hill to Silver Lake, and they’ve been seen on everyone from Julianne Moore to Michelle Williams. To quote writer Lauren Mechling (who likely coined the term clogerati), “They’re the priciest, yes, but the most pleasing to the eye … you could say they’re the Manolo of the increasingly crowded klompen field.” What you may not know is that No. 6 makes clog boots that are around the same price range as Swedish Hasbeens. At $420, they’re not exactly cheap. If you wait long enough (and stock willing), you can get them at the store’s annual sample sale. Writer Alexis Cheung did just that, 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. And you don’t even need to wear socks with them. Shearling-lined, “they’re like mittens for your feet.” Just note that “the heel is a bit tippy.” (It measures 2.5 inches exactly.) Cheung adds, “I always grab a stair railing for fear of falling. But other than that, I find them easy to walk in.”

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