16 best knee-high boots, per stylists | CNN Underscored

Nov 08, 2024

Knee-high boots are the MVPs of fall footwear. They’ll help you look polished and put-together, even if you’re just throwing them on with your favorite leggings, plus they’ll stand up against the cool temps and wet conditions of winter. Investing in a quality pair will no doubt get you through this fall and beyond. To find the ones that are actually worth your money, I consulted professional stylists and a podiatrist for the best knee-high boots that balance comfort, style and practicality.

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"These classic knee-high riding boots have a timeless look while offering durable, quality leather," says fashion stylist Catherine Bibeau. "Not only do they make for a practical and casual look, but you can also dress them up or down."

I found these boots comfortable straight out of the box, and I've spent many days dashing around New York City in them since. They have a reasonable heel height and the pointed toe silhouette looks great with pants, dresses and skirts. I especially love the Plus, the style comes in extra-wide calf sizing for a comfortable fit.

These are board-certified podiatrist Dr. Elizabeth Daughtry's very favorite knee-high boots, which she says she wears all the time. Daughtry highlights their comfortable and supportive fit with a"flexible, removable, anatomic cork and latex footbed wrapped in suede which molds to the shape of your foot," adding that they "will allow you to be stylish and fashionable all day long without any toe pain or pain to the ball of the foot."

"Nine West makes a variety of knee-high boots that are very stylish, affordable and comfortable while also offering options in a wide calf," Daughtry says. The podiatrist recommends this pair, which are technically over-the-knee and feature a stretchy panel and pull tab to assist with pulling the boots on. "With a low heel and more rounded toe box, this boot is a good option for those that need extra room in the toe box," she says.

"Following the chocolate brown trend, this option is great to dress up or down," says Chicago-based stylist Katie Schuppler. The sleek boots have a square toe and straight shaft, although reviewers note that they have a slimmer fit.

With a low heel and slouchy shaft, these boots combine a couple of trends that the stylists called out. "Relaxed, slouchy boots are popular for their casual yet chic appearance and are perfect for pairing with dresses and skinny jeans," Bibeau says. On sale for under $100, this pair is minimalist and chic. The boots are made with vegan leather and come in three colors, including trending burgundy and chocolate brown.

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Bibeau recommends these Sam Edelman boots, calling out their block heel and comfort. They come in six smooth leather and suede options.

I had been lusting after a pair of Frye boots since I first read Nina Garcia's "The One Hundred: A Guide to the Pieces Every Stylish Woman Must Own" back in 2010. I finally splurged and added these to my collection this year and they quickly became my go-to knee-high boots. The 13-inch shaft height is a bit shorter than other knee-high boots, but I found this to be ideal as a petite person. They're made with a durable, structured leather that will only get better with age. I would recommend getting them resoled with a rubber sole as they can be a bit slippery, though.

One of Daughtry's picks, she says these leather knee-high boots have a round toe and reasonable 1.2-inch heel, plus decorative straps and buckle details to elevate the look. "The side zipper closure makes slipping the boot on and off much easier than the traditional pull-on style boots," she adds.

Schuppler says these flat boots from luxury brand Stuart Weitzman "are a great everyday option and for walking around during the cooler months while still being comfortable."

Director of social Stephanie Griffin hopped on the "coastal cowgirl" trend with the Abby boots from Tecovas. They're perfect for adding a country flair to any outfit, built to last and tshockingly comfortable. I can also vouch for Tecovas as one of the comfiest boot brands I've ever worn — there's no breaking-in needed, which makes the high price tag feel a bit more justified.

"Chunky heels and boots with thick block platforms offer both comfort and a bold look, making them versatile for various outfits," Bibeau says. Daughtry likes this pair, which have a higher 2.75-inch heel, but remain comfortable thanks to a stacked block heel and cushioned footbed. The podiatrist says the style is great for "helping you travel from day to night with ease."

"This pair is a chic, metropolitan take on a cowboy boot and would be amazing paired with jeans or leggings, or dressed up with a sweater dress," Schuppler says.

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If you're looking for a pointed-toe boot, Bibeau says to go with these. "Perfectly paired with a dress or a classic pair of pants, these boots have such a sophisticated look to them," she says.

I've largely avoided stiletto heels, so I was pleasantly surprised to find out how comfortable these boots are — and they have a considerable 3.5-inch heel. They are made with a special, arch-supporting insole that actually makes a difference. I have the Natural Snake color, which adds a bit of attitude to my look, but I'd also love the clean Black Calf leather.

"For those looking for a Western boot, Ariat is the boot that I recommend most often," Daughtry says. "The Casanova Western boot offers a resoleable Goodyear leather welt construction, a wide width option and ATS technology that provides ergonomic support on uneven terrain. This fashionable but functional boot is beautiful, comfortable and long-lasting."

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If comfort is your priority, Daughtry has several suggestions for how to find the best knee-high boots for you. The podiatrist recommends sticking to boots that have a maximum heel height of two inches, as anything higher “can place too much pressure on the ball of the foot, leading to metatarsalgia (pain and inflammation in the ball of the foot).” She also suggests looking for a cushioned footbed, ideally with arch support, and boots that are made with a leather or mesh upper “that will stretch and accommodate for any toe deformities, especially if the toe box is more pointed.”

For those with larger calves, Daughtry says riding boots and cowboy boots “tend to be more comfortable and forgiving,” while also offering more room for thicker socks. As for things to avoid, Daughtry says, “The more ‘fashionable’ leather boots with side or back zippers can be uncomfortable or difficult to wear if your calf is large or your ankle is larger or smaller than a ‘standard’ ankle.”

Since quality boots can be pricey, Schuppler says to play it safe and “look for something that is a classic style so that it can be a staple in your wardrobe. She also has advice if you live in a snowy climate: “Opt for a leather option over a suede to maintain the quality of the boot.”

The following FAQs have been answered by board-certified podiatrist Dr. Elizabeth Daughtry and professional stylists Catherine Bibeau and Katie Schuppler.

“Depending on the style of the boot, I would err on side of going up a size, as this will allow for different types and thickness of socks to be worn if the boot is slightly large compared with a shoe that is too small,” Daughtry says. And like any savvy shopper, she notes that it’s worth reading the reviews of the boots you’re interested in if you’re ordering online and aren’t able to try them on before purchasing, as well as checking the exchange and refund policies in case you end up needing a different size or wanting to return them.

Daughtry recommends crew-length or knee-high socks “as smaller, no-show or ankle socks will not be able to protect the bony prominences of the ankle joint to prevent issues or pain or even blisters when wearing boots that go up to the knee.” On top of that, Bibeau suggests opting for lightweight socks that will allow the feet to breathe.

According to the stylists, fitted pants, like skinny jeans or leggings, work best with knee-high boots since they will fit snugly into the boot. Bibeau says this creates a streamlined silhouette. Alternatively, Schuppler says tights and a dress or skirt also look great with knee-high boots.

For this article, we consulted the following experts to gain their professional insights.

CNN Underscored editors thoroughly test all the products we cover and provide full transparency about how we test them. We have an experienced team of writers and editors who have many years of testing experience and ensure each article is carefully edited and products are properly vetted. We talk to top experts when it makes sense to ensure we are testing each product accurately and speaking about pros and cons of each item. For this article, we spoke to professional stylists and a podiatrist to learn as much about picking comfortable yet stylish knee-high boots.

Sophie Shaw is Underscored's beauty and fashion editor. The Brooklyn-based journalist loves getting nerdy about skin care and, on the fashion side, delving into what viral trends are actually worth trying. (Ballet flats are a yes for her, but low-rise pants are a never.)