IE 11 is not supported. For an optimal experience visit our site on another browser.

14 knee-high boots to wear this winter and how to style them

These statement-making boots are equally stylish and comfortable.
TODAY Illustration / Looks Like Summer / DSW / Thursday Boot Co.

Shop TODAY is editorially independent. Our editors selected these deals and items because we think you will enjoy them at these prices. If you purchase something through our links, we may earn a commission. Items are sold by retailer, not TODAY. Pricing and availability are accurate as of publish time. Learn more about Shop TODAY.

Plunging temperatures are a great excuse to don our most fabulous (and coverage-prioritizing) fashion pieces. But when it comes to footwear, nothing brings more excitement than pairing your cloud coat and snow-appropriate attire with knee-high boots.

While this shoe style has been spotted on many celebrities and off the runway since early fall, knee-high boots have been a perennial cold weather go-to thanks to its natural functionality and elegance. Not only can they elevate any ensemble, they also elongate your legs — which is always a plus!

Whether you prefer to wear a flat heel or something a little higher, Shop TODAY asked wardrobe stylist Jacquie Trevizo and New York-based stylist Gianna Nucci for tips on how to wear knee-high boots this season.

How to choose the right knee-high boots

One of the first steps to consider before you invest in new winter boots is to think about your environment. Do you live in a place that has more rain or snow? Do you need boots that are both warm and weatherproof? These are questions Nucci suggests you ask yourself to find a great pair that’s both "stylish and functional."

Secondly, think about your daily lifestyle and the type of footwear you want to match with your wardrobe. "Maybe you have a lot of walking on your commute, so would need a more durable style that’s also comfortable," added Nucci.

If you're in the market to splurge on knee-high boots, make sure they are "versatile and timeless," shared Trevizo. "Warmth is crucial when you consider where you’re based. If you live in a [very cold] area, maybe consider a boot that is lined with faux fur. If you’re in a city where it rains often like Seattle or Miami, it's good to consider boots that have some waterproof factor to them — like [rubber]."

If your town or city has sludge and puddles to overcome this season, Nucci says there are "a lot of cute winter boots that aren’t functional for rain and snow, so you want to be sure you’re not just buying off aesthetic." For example, while leather boots are stylish, these are not easy to clean. Instead, Nucci advised looking for boots with "flannel, sherpa or [insulation features] for those who live in colder climates."

How to style knee-high boots

For the day

Both stylists agree that knee-high boots can be worn day or night. For a chic daytime look, Trevizo opts for a tunic-style sweater, stockings and a roomy trucker jacket. "For New York weather in March, [add] a quilted long coat layered over that oversized trucker jacket, throw on a cute hat and you’re all set."

One of Nucci's favorite casual daytime outfits to style with knee-high boots is "pairing them with leggings, a faux leather or thick ponte knit fabric and a chunky sweater. For a more elevated look, wear them with skinny jeans, so they tuck better, and a structured jacket like a blazer layered over a thin knit."

For the night

For the evening, Nucci loves wearing a knee-high boot with tights and a midi dress or skirt. "I would also recommend a heeled style for the evening. Whether it’s a one-inch bock heel or a stiletto, a heel always makes an outfit dressier."

As for Trevizo, a black monochrome look will complete your night out attire. "Whether it be a bodysuit or a little black dress accompanied by your knee-high boots, [this will look more provocative]. Go all out and do an oversized blazer or faux leather jacket for Los Angeles weather or choose a long trench coat or faux fur coat if out in New York."

What boot styles are trending this season?

According to Trevizo, the boot styles trending this season are equestrian-inspired knee-high boots, suede leather boots, knee-high boots with a pointed toe and chunky block heel or knee-high boots with a kitten heel.

Additionally, there is a higher interest in a lugged sole trend that "carry into 2022, as well as the skin-tight styles that [really] hug the calf," said Nucci. Other trends that continue to dominate street style are western-inspired boots and over-the-knee designs.

Here are the most stylish knee-high boots for winter — curated based on our experts' recommendations — so you make a statement through every stride.

Best knee-high boots, based on expert insights

Universal Thread Lainee Heeled Scrunch Boots

Keep it versatile with this affordable design that comes in a neutral taupe color. You can never go wrong with a classy pair that transitions from day to night.

Marc Fisher Renn Over the Knee Boots

If you're looking for extra coverage, opt for these over-the-knee boots from Marc Fisher. This style won't slouch and will hug your legs all the way up, and the modest block heel makes navigating around much easier. Plus, according to Macy's shoppers, these hold up perfectly even if you have skinny legs.

Circus by Sam Edelman Dinah Lace-Up Lug Sole Combat Boots

For an edgier vibe, consider these boots that reverberate '80s style. The chunkier the better when it comes to combat boots, particularly when that style reminisces Dr. Martens.

Journee Collection Vellia Knee High Boots

This kitten heel boot won't exhaust you when you're walking around town. It comes in four different colors to style day or night — plus it'll be a great pair to transition into spring.

Asos Carla Chunky Flat Boots

Avoid slushy sidewalks with these chunky boots made with a lugged sole. This boot trend continues to control street style and is the perfect addition to your casual winter wear, especially if your city is covered in snow.

Journee Collection Therese Wide Calf Boot

This western-inspired boot comes in three flattering hues, including one of 2021's hottest colors. The boots feature a deep V detailing on the edge, pointed toes and are equipped with Tru Comfort Foam insoles for a cushier walk.

Dune Tawn Faux Shearling-Trimmed Knee-High Boots

For those days when you need protection and style, opt for these leather boots featuring shearling details. The pair has a two-inch high heel to walk in comfort and zip fastening.

Boston Proper Suede Over-The-Knee Boot

With dozens of five-star ratings, this pair from Boston Proper is your go-to style for daily wear. Pair them with Y2K-inspired trends like low-rise jeans or a tulle skirt for a maximalist look. "I wore them at a party with lots of standing with no discomfort," shared one reviewer about how convenient they are to wear.

Sam Edelman Larina Waterproof Knee High Platform Boot

Keep your feet dry in these waterproof knee-high boots from Sam Edelman. Available in four versatlie colors, these are made with a leather upper synthetic lining that won't deteriorate and keep your legs cozy. "They kept my feet warm and dry in snowy Dillon, Colorado," shared one Dillard's shopper.

Looks Like Summer Trinity Knee High Boots

These boots combine comfort and style while keeping your legs warm during winter. The style features a back lace-up detailing and rubber sole to walk with confidence in the snow.

Nine West Hiya Heeled Boots

Slay your way into the freezing atmosphere with these sleek boots from Nine West. The pair is available in four neutral colors with a western-inspired pointed toe. Wear it with a sweater dress and trench coat for a polished vibe.

Thursday Boot Co. Tempest

Look elegant on your next night out with these over-the-knee boots made with ultra-suede fabric. The boots feature anti-slip, shock-absorbing soles and a pull-on style with form-fitting material.

Dolce Vita Solei Boots Whiskey Nubuck

Embrace your inner cowgirl with these western-inspired boots. They come in three neutral colors, plus they feature a manageable two-inch heel for easier strides. P.S. Customers have noted its snug fit, so size up if you need.

Overland Major Shearling-Lined Waterproof Suede Boots

For ultimate functionality, choose these waterproof boots made with a Merino shearling lining. Not only does it have a feminine, comfortable construction, but it can also withstand temperatures up to -13°F.

Chiara Ferragni Hearts Combat Boots

Made of 100 percent calf leather, these boots are definitely a conversation starter. The pair features a platform sole and rounded toe for a comfortable fit. These boots will give you overexposure wherever you go.

For more stories like this, check out:

Subscribe to our Stuff We Love and One Great Find newsletters, and download our TODAY app to discover deals, shopping tips, budget-friendly product recommendations and more!