The Best Knee-High Boots, According to People Whose Taste We Trust

By far the most inexpensive of the bunch are these boots by Aerosole recommended by creative directorHannah 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.

StylistCharline Zeroualalso likes the brand Aerosoles 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.

“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. Curly-hair content creatorKristian Spragginsowns a pair of them in red and says they’re her favorite comfortable boots to wear in the late summer into fall.

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.

I’ve had these for about six months now, and they’ve become a shoe I reach for when I want to make a statement. I usually wear them under midi- and mini-length skirts and dresses and love that they look almost like an edgier riding boot.The square toe and slight platform lug sole feels like classic Doc Martens to me without being too obvious it’s from the brand. I’m typically a size 6.5 and sized down to a 6, which fits me perfectly. The one thing I’ll note, though, is these aren’t for folks with wider calves.

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 Studiofounder 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.

I’ve had these Vagabond boots for a little over two months now, and they’ve quickly become some of my favorite shoes. Right out of the box, I was able to walk all day in these without any pain. I especially like how comfortable the shaft of the boot is. It’s very fitted but has enough stretch so it never feels suffocating. The tight fit also lets me wear the boots underneath jeans and pants without the shaft sticking out near my knee (a pet peeve of mine). The rest of the shoe is designed just as comfortably: The square toe isn’t too blocky but roomy enough so that my toes never feel cramped and the heel is a breeze to walk in.

While technically a rain boot, personal stylist and Kule content directorElizabeth Tamkinsays these are unexpectedly versatile. She’s worn them in rain, shine, and even snow, since she’s not a fan of bulky snow boots. They’re made with a high-grade natural rubber and lined with a polycotton jersey lining that’s moisture-wicking and fast-drying.

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 wait lists 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.

Strategist writerBrenley Goertzenhas 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.

“Page Six” style and shopping directorElana Fishmanwears 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 one of the steepest price points on this list, but they’re highly recommended by two folks I spoke to. Fashion writer and content creatorAlyssa Coscarellisays 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 writerJo 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.

Laurel Pantin, creator of theEarl Earlnewsletter, says her most recent favorite pair of knee-highs are these barely there boots from Co. “They’re so thin that they kind of disappear up your leg,” she says, noting she’s worn them with midi-length skirts and dresses, as well as cropped trousers. They were one of the two shoes she wore during this most recent Paris Fashion Week, since they’re stylish, light, and comfortable.