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 maxi dress and faux leather jacket with knee-high boots.
While this shoe style has been spotted on many celebrities and off the runway every 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 boots is to think about your environment. Do you live in a place that has more rain or snow in the winter months? 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 fall— curated based on our experts' recommendations — so you make a statement through every stride.
Best knee-high boots, based on expert insights
Keep it versatile with this affordable design that comes in a neutral tan color. You can never go wrong with a classy pair that transitions from day to night.
Western-style boots rose in popularity last year and are seemingly here to stay. Hop right onto the trend with these tall embroidered boots that go with everything, according to reviewers. One Amazon shopper says they keep your feet very warm which is perfect as temperatures start to drop.
A classic tall riding boot is a must-have in any fall wardrobe. This style also comes in black and features a lugged sole that's both trendy and functional.
On the days you want to prioritize fashion over function, you can't go wrong with these slouchy over-the-knee boots from Macy's in-house brand INC International Concepts. Other stylish features include almost a four-inch high stiletto heel (inexperienced heel-wearers beware), a V-notch cutout in the back and memory foam inside.
Keep your feet dry in these waterproof knee-high boots from Aerosoles. Available in three neutral colors and two finishes, these are made with a rubber upper synthetic lining that won't deteriorate and keep your legs dry.
A black riding boot can easily be dressed up with your favorite maxi dress or maxi skirt or kept casual with a cozy jeans/sweater combo.
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.
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.
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.
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.
This western-inspired boot comes in three flattering hues, including one of last year'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.
These boots combine comfort and style while keeping your legs warm. The style features a back lace-up detailing and rubber sole to walk with confidence in the snow.
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.
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.
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.