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Compared with the leg-lengthening thigh-high or the equestrian over-the-knee, the ankle boot may be less statement-making. But what it lacks in height, it makes up for in versatility — we’d be willing to bet that if there’s one style of shoe you can slip on from late August through mid-May, it’s an ankle boot. Like all wardrobe basics, whether a white button-down or a black T-shirt, there’s a vast sea of options to wade through before landing on the right ones. So to find the best ankle boots, I asked opinionated shoe obsessives about the pairs they rely on — and tested a couple of the styles they mentioned for myself. To ensure any noteworthy footwear wasn’t missed, I also searched our archives for other boots worthy of being named the very best of the best.
What we’re looking for
Size range
As usual, we’re on the hunt for a large size range.
Material
Caring for a frequently worn boot is a Sisyphean responsibility — the more you wear it, the more it looks worn. But how long a pair lasts comes down to two things: what they’re made of and whether they’re waterproofed. Not all ankle boots can handle precipitation right out of the box (only one on this list is water-resistant), but fortunately, this is a pretty easy fix with the right waterproofer, which you can spray on yourself (Tarrago is our best overall pick).
Design details
The ankle-boots category covers a lot. Anything with an ankle-high shaft counts — no matter the shape of the heel, heel height, or other details like zippers on a specific side (as opposed to Chelsea boots, a kind of ankle boot that always has a lower heel and elastic at the sides). To make sense of it all, we looked at the design of every pair of ankle boots recommended to us, searching for the details — from stitching to the shape of the sole — that make each one special.
Price
We ranked every pick below by affordability — $ for those $150 and under, $$ for $151 to $300, and $$$ for anything over $350.
Best overall ankle boots
Sizes: 5–12 | Material: Leather | Design: ½” platform, lug sole, pull tab, Docs stitching | Price: $$
Docs are the gold standard for ankle boots, according to those we talked to, and the 2976s are its original Chelsea, manufactured since the 1970s. New York Review Books marketing manager Abigail Dunn describes the style as subtler than some other showier Docs for their lower-profile, translucent sole and matte leather. (Though if you want something flashier, you can also get them with a faux-fur lining or a platform.) The boots are utilitarian and versatile, which Jenni Lee, founder of sock label Comme Si, appreciates: For her, they double as slush-fighters in the winter and rain boots in the spring.
Hannah Baxter, former deputy beauty editor of the Zoe Report, credits good ol’ British craftsmanship for the boots’ durability. But Docs are notoriously stiff at the start — Dunn recommends slathering on the brand’s Wonder Balsam to soften the leather and make it “pretty much indestructible.” After starting to wear the 2976s myself, I absolutely suggest taking your time to break them in without literally hurting yourself. I have been layering two crew socks as I get the shoes stretched out, and it’s worked well so far — the boots are easier to pull up and becoming more comfortable by the day. And while I have wider feet (a struggle I’ve chronicled on this very site), the 2976s are accommodating, with room for my toes to wiggle around. Come winter, I’ll be ready to wear them everywhere.
Best chunky ankle boots
Sizes: 5–11 | Material: Rubber | Design: 1 ½” heel, 1-inch platform, lug sole, toe cap | Price: $$
Ganni — or the “Danish Mansur Gavriel,” as we dubbed the label — makes tactical-looking boots that Taylor Tomasi Hill, creative and fashion director of the Yes, and fashion content creator Tilly Macalister-Smith both love. This recycled-rubber style comes recommended courtesy of Macalister-Smith, who says that though they look high-end, they don’t have a high-end price tag — that’s why she was willing to make an exception to her secondhand-shopping habit for them. Macalister-Smith describes them as undestroyable and capable of handling everything from snowy streets to garden exploits. The shoes are so comfortable they rival sneakers — remarkably, she says she didn’t have to go through a real breaking-in process with them.
Best platform ankle boots
Sizes: 5–12 | Material: Leather | Design: Branded pull tab, 2” heel, 1 ½” platform | Price: $$
This is the platform version of the 2976s that earned our Best Overall title. Lisa Sokolov, co-founder of Social Goods, bought these boots out of nostalgia — she has been wearing Docs on and off since middle school. The chunky one-and-a-half-inch platform and two-inch heel give her a little more height, but that boost doesn’t detract from how easy these are to walk in. This isn’t the first time we’ve heard about them, either — Elizabeth Tamkin, content and partnerships manager at Kule, is another fan of the thicker-soled Docs.
Best lace-up ankle boots
Sizes: 5–11 | Material: Leather | Design: 1 ¼” heel, 8-eye lace-up, brand’s signature stitching | Price: $
The 1460s were introduced in 1960 — and since then, the lace-up style has earned quite the following, favored by the likes of the Clash and even the glitterati. Here at the Strategist, we’ve heard about them from hairstylist Cassadi Currier and Catbird chief creative officer Leigh Plessner. Currier wears hers to work since they’re slip-resistant — when there’s water on the floor, she knows that “if I want to walk through it quickly, or if I have to, I’m not gonna fall and die.” The patent-leather 1460s in particular fulfill Plessner’s passion for shiny black shoes, toughening up nightgowns and dressing up sweatsuits. Strategist writer Dominique Pariso is our third devotee — she has been relying on her 1460s every winter since she was a teen. “Pair them with a wool sock and they are guaranteed to keep your feet warm and dry,” she says.
Best combat ankle boots
Sizes: 5–12 | Material: Leather | Design: Lace-up front, side zipper, 2” heel, 1 ¼” platform | Price: $$
Docs’ Jadon line of lace-up platforms is a favorite of three celebrities, each of whom named a pair as one of the things they can’t live without. The Jadon 8-Eye Boot was name-checked by actress-singer Dove Cameron and YouTuber Emma Chamberlain, who considers these nothing short of life-changing. “They give me a rock-star feeling, like I could stomp on a drum set with my boots if I wanted to,” she explains, adding that they “take every outfit from ‘that’s cool’ to ‘whoa, look at her.’” Cameron seconds that sentiment: She fell in love with hers on the set of Marvel’s Agents of S.H.I.E.L.D., where she had to gear up in tactical clothes as a villain. Off-screen, she has been known to stuff sweats and too-long jeans into the tops. For more height, model Georgia May Jagger recommends the Max version of the shoes, which she says act as “I mean business” armor thanks to their even thicker sole.
Best block-heeled ankle boot
Sizes: 35–41 (equivalent to US 4–10) | Material: Leather | Design: 2 ½” block heel, square-toe | Price: $$$
The Lazaros are LoQ’s signature block-heeled boot, with a square toe and zippered sides. Bathen co-founder Hannah Zisman likes that the square toe has rounded edges that keep it from looking too severe. And while they’re an investment at $395, I know from experience that they’re well constructed — made in Spain from a supple leather that doesn’t scratch too easily, and I’ve never felt wobbly while walking in them. With a 2.5-inch heel, they are quite comfortable to wear for longer stretches — I’ve been testing them on and off since July. And Ouisa founder Bryn Taylor actually describes the Lazaros as slipperlike on the comfort scale, though it can take a minute to get there: Strategist writer Lauren Ro, who also owns a pair, explains that the opening at the ankle is tight at first, but stretches after a few wears. Even as someone with wider calves, I didn’t find the boots too challenging to break in. Just remember to size up, per LoQ’s own instructions, as its sizing is based on European conversions. For reference: I often size up from my usual 7 to an 8 when buying boots, and requested a 39 from the brand for testing.
Best square-toed ankle boots
Sizes: 35–44 (equivalent to US 5–13) | Material: Leather | Design: 3” block heel, slim shaft, pointed square-toe | Price: $$
These West boots from Alohas are another one of Hill’s favorites. The square toe straddles the line between fresh and classic, she says. And while the toes on the LoQ Lazaros, above, have a curved edge, the toes on these are sharper with a more western look, contrasting with the sculptural block heel. Hill also shouted out the brand’s “on-demand” production model, with some styles available for preorder at a discount, so the brand knows how many pairs to make. Depending on the size and color you choose and when you order, you can get them for up to 40 percent off — just double-check the expected shipping dates, which can vary depending on which production “phase” the boots are in.
Best pointed-toe ankle boots
Sizes: 35–41 (equivalent to US 5–11) | Material: Leather | Design: 3” block 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 every so slightly squared at the end, giving its shoes a “subtle western vibe,” Taylor says. 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 Leandra dresses up the most casual of outfits with its glossy finish.
Best (less expensive) pointed-toe ankle boots
Sizes: 5.5–11 with half sizes | Material: Leather | Design: Western-style, 2 ½” stacked block heel | Price: $
These are a more affordable alternative to the Leandras with a much more dramatic pointed toe. Style coach Kim Hancher likes to wear them with bootcuts and flares so the toe peeks out. She says she gets compliments whenever she steps out in them. For her “ailing feet,” the chunky stacked block heel sits at the right height and offers more stability than a spikier one. These boots come in a number of shades, prints, and textures, including cow and leopard — Hancher went with a beige-and-tan snakeskin that she says makes these look more expensive than they are.
Best sock ankle boots
Sizes: 5-11 with half sizes | Material: Polyester, nylon, elastane | Design: Ribbed detail, 2” heel | Price: $
The Glove Boot may be one of the cheaper pairs on this list, but that doesn’t mean it’s any less worthy. It 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 — 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.
Best rugged ankle boots
Sizes: 5-11 with half sizes | Material: Water-resistant leather | Design: Double pull tabs, lug sole | Price: $$
There has been much Blundstone praise on the Strategist, but the 500s in particular were a big hit with the stylish people we talked to. Jo Zasloff, co-founder of skin-care line Sisters, sums it up best: These are a perfect everyday boot. Emily Vaca, founder of the inflatable-pool purveyor Minnidip, considers these Blunnies (“as the cool kids call them”) a true workhorse. She wears them with Dickies for warehouse work and then out for cocktails once she’s off the clock. Dancer and consultant Eva Alt uses these to survive slippery city walks. And audio producer Amy Pedulla likes how they get better with age, becoming a “smudgy, comfy glove on your feet.” Pedulla let us in on this industry secret, too: Nearly everyone in podcasting wears a pair of Blundstones. For her part, Pedulla relies on them for schlepping audio equipment around between studios.
Best cowboy ankle boots
Sizes: 5-12 | Material: Leather or suede | Design: 2 ½” heel, snipped toe, toe-bug stitching | Price: $$
For a true cowboy-style ankle boot that’s not an Ariat, go with a pair from Tecovas, a favorite of two Strategist staffers. Milliner-Waddell says that with her wider feet, boots are oftentimes hit-or-miss, but the Daisys (full disclosure, they were a gift) were comfortable from the moment she slipped into them. Pariso was also surprised to find the Tecovas didn’t need to be broken in — a feat considering that, as someone with wider calves, she usually doesn’t have enough space in boots.
Some more ankle boots we’ve written about
Our experts
• Eva Alt, dancer and consultant
• Hannah Baxter, deputy beauty editor of The Zoe Report
• Dove Cameron, actress-singer
• Nana Castro, blogger-TikToker
• Emma Chamberlain, YouTuber
• Cassadi Currier, hairstylist
• Iva Dixit, New York Times Magazine editor
• Abigail Dunn, New York Review Books marketing manager
• Kim Hancher, style coach
• Freddie Harrel, founder of beauty company RadSwan
• Taylor Tomasi Hill, creative and fashion director of the Yes
• Georgia May Jagger, model
• Christel Langué, stylist
• Jenni Lee, founder of luxury sock label Comme Si
• Tilly Macalister-Smith, fashion content creator
• Jenna Milliner-Waddell, Strategist associate editor
• Dominique Pariso, Strategist writer
• Amy Pedulla, audio producer
• Leigh Plessner, Catbird creative director
• Alisa Richter, head of public relations at the Sill
• Lauren Ro, Strategist writer
• Nozlee Samadzadeh, New York Times senior software engineer
• Lisa Sokolov, co-founder of Social Goods
• Bryn Taylor, founder of Ouisa
• Emily Vaca, founder of inflatable-pool purveyor Minnidip
• Kiane von Mueffling, Sold Out NYC founder
• Jo Zasloff, co-founder of skin-care line Sisters
• Hannah Zisman, Bathen co-founder
Additional reporting by Hilary Reid and Jenna Milliner-Waddell.
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