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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, we asked opinionated shoe obsessives about the pairs they rely on. And to ensure we didn’t miss any noteworthy footwear, we searched our archives for other styles worthy of being named the very best of the best.
What we’re looking for
As usual, we’re on the hunt for a large size range.
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).
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.
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: $$
Docs are the gold standard for ankle boots, according to our panelists, and the 2976s are its original Chelsea. New York Review Books marketing manager Abigail Dunn calls the 2976s a go-to for their subtlety compared with some showier Docs, thanks to a barely there platform and almost matte leather. Jenni Lee, founder of luxury sock label Comme Si, mentions that these are functional on top of their timelessness — they work as a slush-fighting machine in the winter and a rain boot in the spring. They also earned a spot in our guide to the best Chelsea boots, with Freddie Harrel, founder of beauty company RadSwan, relying on the 2976s for an “extra-badass edge.” (A pro tip to know before we go on: Docs are notoriously stiff at the start, so Dunn recommends slathering on the brand’s Wonder Balsam to help soften them up and make them “pretty much indestructible.”)
Best Chelsea ankle boots
Sizes: 5–11 | Material: Leather | Design: Glossy finish, 1” block heel | Price: $
The Floras are the pair we heard about most in the aforementioned Chelsea-boots guide. New York Times Magazine editor Iva Dixit says their streamlined sole “makes them feel a little more adult.” New York Times senior software engineer Nozlee Samadzadeh also attributes their grown-up vibe to the flatter heel, which keeps them from looking like the taller Docs out there. Their lower height is practical, comfort-wise, and Strategist associate editor Jenna Milliner-Waddell says she has yet to step into a puddle or pile of snow these boots couldn’t handle. Every expert who recommended the Floras agrees that the boots are long-lasting, too. The mirrorlike finish gradually develops a patina that makes them seem pre-loved as opposed to worn out, Dixit mentions. Hannah Baxter, deputy beauty editor of The Zoe Report, credits good ol’ British craftsmanship for their durability.
Best chunky ankle boots
Sizes: 5–11 | Material: Rubber | Design: 1 ½” heel, 1-inch platform, lug sole, toe cap | Price: $$
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: $$
This is the platform version of the 2976s that earned our Best Overall title. Lisa Sokolov, co-founder of Social Goods, bought these boots out of nostalgia — she has been wearing Docs on and off since middle school. The chunky one-and-a-half-inch platform and two-inch heel give her a little more height, but that boost doesn’t detract from how easy these are to walk in. This isn’t the first time we’ve heard about them, either — Elizabeth Tamkin, content and partnerships manager at Kule, is another fan of the thicker-soled Docs.
Best lace-up ankle boots
Sizes: 5–11 | Material: Leather | Design: 1 ¼” heel, 8-eye lace-up, brand’s signature stitching | Price: $
The 1460s were introduced in 1960 — and since then, the lace-up style has earned quite the following, favored by the likes of the Clash and even the glitterati. Here at the Strategist, we’ve heard about them from hairstylist Cassadi Currier and Catbird chief creative officer Leigh Plessner. Currier wears hers to work since they’re slip-resistant — when there’s water on the floor, she knows that “if I want to walk through it quickly, or if I have to, I’m not gonna fall and die.” The patent-leather 1460s in particular fulfill Plessner’s passion for shiny black shoes, toughening up nightgowns and dressing up sweatsuits. Strategist writer Dominique Pariso is our third devotee — she has been relying on her 1460s every winter since she was a teen. “Pair them with a wool sock and they are guaranteed to keep your feet warm and dry,” she says. Though keep in mind that the 1460s are “famously stiff to start,” according to the company.
Best combat ankle boots
Sizes: 5–12 | Material: Leather | Design: Lace-up front, side zipper, 2” heel, 1 ¼” platform | Price: $$
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 with half sizes (equivalent to US 5–10) | Material: Leather | Design: 2” block wooden heel, square-toe | Price: $$$
Alisa Richter, head of public relations at the Sill, got these block-heeled Coclico boots as a replacement for a pair of old, overworn A.P.C.s. Made in Spain from Italian leather, the Jujus are decidedly austere in appearance, featuring a heel fashioned from solid wood and a squared toe. Like other pairs designed by New York City–based shoemaker Coclico — Richter has been a loyalist to the company, collecting a number of their sandals over the years — these are “impeccably well made and have a subtle ’70s vibe,” she says. She adds that the boots are “an investment piece but will anchor my wardrobe for many seasons to come.” She says they’ve elevated every outfit she’s worn them with, including ripped Levi’s denim with a top from Sézane and a Cara Cara dress.
Best square-toe ankle boots
Sizes: 35–41 (equivalent to US 4–10) | Material: Leather | Design: 2 ½” block heel, square-toe | Price: $$$
Although they’re an investment, you can’t go wrong with LoQs — among the higher-end labels recommended to us, it was one of the most cited. The Lazaros have a square toe that’s not so severe with its rounded edges, says Bathen co-founder Hannah Zisman. In terms of feel, Ouisa founder Bryn Taylor considers the Lazaros to be slipperlike on the comfort scale, though it takes a minute to get there: As Strategist writer Lauren Ro explains, the ankle opening is tight at first but quickly stretches out after just a few wears. She adds that the practical block heel is neither too high nor too low.
Best (less expensive) square-toe ankle boots
Sizes: 35–44 (equivalent to US 5–13) | Material: Leather | Design: 3” block heel, slim shaft, pointed square-toe | Price: $$
Alohas West Black Vintages are a particular favorite of Hill’s because the square toe straddles the line between fresh feeling and classic. While the toes on the Lazaros have a curved edge, the toes on these are sharper with a more western feel, which contrasts with the sculptural block heel. Another perk, Hill points out, is Alohas’ sustainable on-demand model, meaning most of its shoes are available for preorder (sometimes at a discount), so the brand knows exactly how many pairs to produce.
Best pointed-toe ankle boots
Sizes: 35–41 (equivalent to US 5–11) | Material: Leather | Design: 3” block heel, pointed square-toe | Price: $$$
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 knit ankle boots
Sizes: 5-13 with half sizes | Material: Knitted from merino wool and plastic bottles | Design: Back pull tab, stretch panels on sides, square-toe | Price: $$
These Rothy’s are knit from a combination of merino wool and the company’s “signature thread” spun from plastic bottles. It was an Instagram post of an “impeccably dressed influencer traveling in Vermont with a toddler” that convinced Richter to get a pair for herself. She’s found them to be exactly what she’s looking for when it comes to boots as they’re flat, easy to slip on, and can “withstand icy New York winters” since the shoes are machine-washable. Plus, the boots are so comfortable that they feel like slippers, requiring zero breaking-in time and weighing “next to nothing.” Richter adds: “These are like wrapping your feet in a cozy merino sweater, but they still look chic.”
Best sock ankle boots
Sizes: 5-11 with half sizes | Material: Polyester, nylon, elastane | Design: Ribbed detail, 2” heel | Price: $
The Glove Boot may be one of the cheaper pairs on this list, but that doesn’t mean it’s any less worthy — stylist Christel Langué and blogger-TikToker Nana Castro both recommend it. The lowish block heel makes these pedestrian-friendly — Langué turns to them when she knows she has a full day of walking ahead because they help her stay as pain-free as possible. Castro is especially fond of the boots’ aesthetic: “These are made from renewed plastic bottles, though you’d never know from the knit look.”
Best rugged ankle boots
Sizes: 5-11 with half sizes | Material: Water-resistant leather | Design: Double pull tabs, lug sole | Price: $$
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
• 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
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