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Throw on a knee-high boot, and it instantly elevates a plain skirt or dress into a full-on outfit. Finding the right pair can be a bit difficult, though. “Tall boots open up more room for mistakes, flaws, and ill-fitting issues,” says stylist Vanessa Valiente. “You’ll often see these sky high heels or a beautiful shoe that doesn’t necessarily move beautifully.” On top of that, the prices for taller boots will typically cost you at least a hundred bucks, so they’re more of an investment, than say, ankle boots or sneakers. I went in search of the ones that are actually worth it and spoke to stylists, founders, content creators, and other fashionable folks about their personal favorites. You’ll find everything from snake skin kitten heels to boots for every calf size. And if you’re in search of even more shoes, we have some handy guides on the best women’s winter boots, rain boots, and Chelsea boots.
Under $250
By far the most inexpensive of the bunch are these boots by Aerosole recommended by creative director Hannah Black. “I find them to be just as comfortable as my flat Sketchers,” Black says, adding that the memory foam and soles make staying on her feet for hours at a time a breeze. The shaft is the right amount of stretchy, but if you’re worried about it fitting your calf, they also offer it in wide sizes. Black also called out the fashion-forward square toe and versatility of the shoe. “I like to wear them with a midi skirt because they’re cute enough to show off, but they do look nice under a wide leg pant,” she says. The boots are cheapest at Aerosoles’ site with limited size options, and Amazon carries them for under $100 with more colors and sizing.
Stylist Charline Zeroual also likes the brand Aerosole for her clients who can’t sacrifice comfort for style. She often recommends these to clients who walk a lot in colder cities, because of the shoe’s cushiony insoles and water- and slip-resistant features. These aren’t available in wider calf sizes, but they do come with a second zipper that widens the shaft fit.
For a similar boot as above that’s made with real leather, Zerousal recommends these from Madewell. A couple thing to keep in mind: they have a slightly lower heel height and shaft height, and they don’t come with an option to widen the calf. But, if these are a fit for you, they’re a steal for leather knee-high boots.
“Sam Edelman’s quality is pretty amazing for the price point,” says Zerousal, who often recommends the brand to her clients on a budget. Both she and Black are fans of the classic-looking Sylvia boot because it comes in a lot of colorway and pattern options and that it’s available in wide-calf sizes. “It’s a sleeker boot for the price,” says Black, adding that the detail in the heel is a nice touch.
If you’re looking for boots that lean Western but don’t scream cowboy, Zerousal recommends these from Quince. “They look pretty amazing,” she says, adding that the quality surpasses the fairly affordable price point. The one thing she notes though is that they may be too tall for petites. “My client who wore them is 5-foot-8. On anyone shorter, these might throw off the proportions,” she says.
Under $500
Zerousal’s a fan of the brand Alohas, because of their sustainability efforts. Rather than over-producing, they encourage customers to pre-order and join waitlists as a way to cut back on waste, she says. Her current favorite from the brand are leather kitten-heel boots with a slouchy wrinkled effect at the shaft. She owns them herself, noting that they’ve held up beautifully and that she often styles them with maxi dresses and silk skirts.
Valiente, also a fan of Alohas, prefers the Rory for its streamlined, modern look. They also have a modest heel, so they’re easy to walk in. And, importantly, she says that these move well. “A shoe can be as beautiful as you want, but it doesn’t matter if it’s going to look ugly or wrinkle poorly when you’re moving,” she says.
If you’ve ever struggled to find a knee high boot that fits just right, Duo boots offers the widest range of sizing on this list. Their boots come in petite, regular, and tall shaft heights, and calf width sizes ranging from 30 to 50 centimeters. Petite Studio founder Jenny Wang is a fan and has had a pair of the Haltham knee-highs for about a year. “They’re so comfortable,” she says. “I can walk in them for hours without any blisters.” She also likes their classic design that makes them versatile enough for dresses, midi skirts, and mini skirts.
Strategist writer Brenley Goertzen has had a pair of these Tony Bianco boots in chocolate brown since last October and has already trekked miles in them through downtown Toronto. “The heel is just so durable, because it’s wider,” she says. “And the heel height is just right: not too tall but not a kitten heel.” She also appreciates that the boots are slightly wider at the top, because they never squeeze her leg and are always comfortable.
Zerousal says Margaux makes some of her favorite boots at the moment. These specific suede ones caught her eye because they’re the “perfect chocolate brown.” And, it happens to be the only round toe boot on this list, which was a big plus for Zerousal. “The square toe is very 2023 or 2024,” she says. “When we can put a year on an item of closing, it’s usually not a good sign. It means it’s not very timeless. Can we put a year on it? No, because it’s super timeless.”
$500 and over
Page Six style and shopping director Elana Fishman wears her Loeffler Randall boots at least once or twice a week during the fall and winter months. The two-inch heel is perfectly walkable, and these didn’t require any break-in time, she says. She also appreciates the pull-on style instead of a zipper, because it adds to its sleek, polished look. “They’re certainly an investment, but in terms of cost per wear, you really can’t beat them,” Fishman says.
These Labucq boots come with the steepest price point on this list, but they’re highly recommended by two folks I spoke to. Fashion writer and content creator Alyssa Coscarelli says they’re a favorite out of all the shoes she owns, because the quality is “such to last a literal lifetime,” they’re flattering for her 5-foot-tall frame, and look great with everything. Artist and writer Jo Rosenthal, who’s had hers since the shoe first came out (about four years ago), echoes the same sentiments. “They’ve become a staple in my wardrobe because they go with everything and can exist in every climate,” she says. “I’ve worn them while meeting camels in California and through many rainy days in Paris.” She’s even convinced her sister and sister-in-law to get pairs, and says they love them just as much.
The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.
