Plunging temperatures are a great excuse to don our most fabulous (and coverage-prioritizing) fashion pieces. When it comes to footwear, nothing brings more excitement than pairing a maxi dress and faux leather jacket with a fall footwear staple: knee-high boots.
Every fall, this shoe style is spotted on celebrities and off the runway, bringing an extra sense of coziness to our outfits. Knee-high boots have been a perennial cold weather go-to due to their natural functionality and elegance. Not only can they elevate any ensemble, but 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 several experts for tips on how to wear this footwear staple.
How to find the right knee-high boots | Boots trending this season | Best knee-high boots | How to style knee-high boots | FAQs | How we chose | Meet the experts
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 Maryland-based stylist Gianna 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," adds Nucci.
If you're in the market to splurge on knee-high boots, make sure they are "versatile and timeless," shares wardrobe stylist Jacquie 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 tends to have a lot of sludge and puddles to overcome, Nucci says there are "a lot of cute...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, they are not that easy to clean. Instead, Nucci suggests looking for boots with "flannel, sherpa or [insulation features] for those who live in colder climates."
Additionally, foot and ankle surgeon Dr. Buck Smith encourages people to try on knee-high boots in the store because "there is so much variability in construction and support between different types and brands of shoes. Certain foot types like flat feet will likely benefit from a wider boot with more support."
What boot styles are trending this season?
"This season, we’re definitely seeing a reiteration of trends from the past which is great because most likely there is something in your closet that will already feel current with fall approaching," shares Nucci.
One trend that continues to dominate street style is Western-inspired boots. "It seems like everyone enjoys adding a little country to their step because the Western trend is here to stay and continues to grow stronger over the years," says Nucci.
To add to its current popularity, Google Trends saw an uptick in cowboy boots-related searches up to 4,100% in the past 30 days. While the versatile boot is one of the most shopped boots in the market, there are some other styles trending and worth giving a try, according to Nucci:
- Lace-up/buckle boots: "Think punk meets moto for this trend that incorporates details like thick soles, buckles and laced-up closures to create a sense of toughness and edge. There is a good variation to this style like a classic combat boot that enables someone to err more on the side of caution, to more dramatic details like big buckles and rugged soles for those looking to fully embrace the style."
- Foldover boots: "Inspired by the classic Givenchy shark lock boot, this is a trend that we haven’t seen in a while and is more fresh to the scene this year. You will see these designed in either a heel or wedge sole."
- Slouchy thigh-highs: "Stepping away from the skin-tight aesthetic they used to be, the new thigh-highs are packed with a baggier volume that can easily be paired with shorter silhouettes like mini skirts, shorts and sweater dresses for fall."
- Denim/silver boots: "Both denim and silver are coming in hot on the shoe scene this year and you’ll see the material and color implemented across multiple shoe categories including boots."
Best knee-high boots, based on expert insights
Embroidered Western Cowboy Boots
- The boots stay up
- Easy to slip on
- They take time to break in
Sizes: 5-12 | Heel height: 2 inches | Colors: 13
Western-style boots rose in popularity this year and are seemingly here to stay. Hop right onto the trend with this tall embroidered pair that goes with everything, according to reviewers.
It features a pull-on style and classic embroidery that matches with most casual pieces. One Amazon shopper even says they keep your feet very warm which is perfect as temperatures start to drop.
Kelly & Katie Sion Riding Boot
- Runs true to size
- Somewhat snug in the ankle
Sizes: 6-11 | Heel height: 1.5 inches | Colors: Black and dark brown
A classic tall riding boot is a must-have in any fall wardrobe. The wide shaft and short heel will support your arches while strutting around the city in this pair, which makes it extra functional. One customer noted these boots were pain-free and cozy.
"I didn't have any blisters or soreness and they're very comfortable."
Journee Collection Jenicca Knee High Boots
- Modest heel for comfort
- Not offered in wide sizes
Sizes: 6-12 | Heel height: 2.5 inches | Colors: 4
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.
Whether it's cold or rainy, you can trust these boots will keep your feet dry thanks to the rubber sole design and block heel. It comes in two different colors to style day or night — plus it'll be a great pair to transition into spring.
Women’s Winny Block Heel Tall Boot
- Stretchy side panels
- Comfortable insoles
- Not suitable for slim calves
Sizes: 6-12 | Heel height: 2.75 inches | Colors: 4
This knee-high heel boot won’t exhaust you when you’re walking around town. With an elastic ribbed knit upper and a block heel, the boot promises a reliable walking experience.
It combines a stretchy construction and Tru Comfort insole technology that will prevent your foot from having extra pressure. Also, it comes with a back zipper entry to make it easy to slip them on.
Journee Collection Therese Wide Calf Boot
- Shaft doesn't slide down
- Narrow toe box
Sizes: 6-12 | Heel height: 3.25 inches | Colors: 5
This Western-inspired boot comes in five flattering hues, including one of last year's hottest colors. They feature a deep V detailing on the edge, pointed toes and are equipped with Tru Comfort Foam insoles for a cushier walk.
If you have extra wide calves, these boots are a smart choice. "These are amazing! They stay up well with a good pair of over-the-knee socks," said one shopper.
Charles & Keith Zip-Up Thigh-High Boots
- Side zippers for easy slip-on
- Tight for wider calves
Sizes: 4-11 | Heel height: 1.7 inches | Colors: 3
Keep your feet warm and dry in these chunky knee-high boots that are made for colder days. They are constructed with a satin lining and patterned soles to give you that extra traction in rainy weather conditions.
According to customers, these boots go higher than expected and are excellent for women with wider calves.
Billini Xylia Boot
- Low stiletto heel
- Not enough arch support
Sizes: 5-10 | Heel height: 2.3 inches | Color: Chalk
The contemporary silhouette adds a chic element to the boots. It's a pair that will be more suitable for city walks when you need to go from the office to an event.
Deals editor Rebecca Brown got a similar pair last year. "I love the low heel, it makes it so much more practical to wear. And they’re so striking with sweater dresses," she adds.
Steve Madden Lassy Foldover Cowboy Boot
- Easy pull-on style
- Runs small and fits snug
Sizes: 6-10 | Heel height: 4 inches | Color: Bone leather
These leather knee-high boots encompass two trends in one: foldover and cowgirl core. According to Nucci, this style can act as a neutral to match almost everything you pair it with. Also, it helps to “add something a bit more exciting to the wardrobe aside from black and beige.”
It features a leather and cotton blend material with a block heel that makes navigating around much easier.
Marc Fisher Fadila Foldover Boot
- Perfect for thick calves
- Padded footbed
- Limited colors
Sizes: 6-11 | Heel height: 3.25 inches | Color: Black
Complement your bottoms and dresses with this design. This boot features a pointed toe, 3 1/2 inches heel and a foldover shaft that adds elegance to any outfit.
"These boots are a great statement piece to add to your wardrobe this fall if you’re looking for something new, and balance with more form-fitting pieces," adds Nucci.
INC International Concepts Iyonna Over-The-Knee Slouch Boots
- Don't slouch down after wear
- Don't offer arch support
Sizes: 5-12 | Heel height: 3.75 inches | Colors: 5
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.
“I have wide feet and thick thighs and calves. Finding boots that fit is usually a struggle. I got these in three colors and I love them! I was able to walk around a convention all day in them and that would be impossible with nearly every other pair of boots I own,” said one shopper.
Looks Like Summer Trinity Knee High Boots
- Lace-up feature to adjust
- Limited sizing
Sizes: 4-9 | Heel height: 1.5 inches | Colors: Brown and black
These chunky boots combine comfort and style while keeping your legs warm and secure. The style features a back lace-up detailing and rubber soles to walk with confidence in the snow.
Plus, you can expand the boot thanks to the lace-up feature on the back. It's a great option if you need extra spacing and a looser feel.
Naturalizer Kalina Wide Calf Knee-High Boot
- Offered in a wide size
- Heel is slightly high
Sizes: 5-12 | Heel height: 3.25 inches | Colors: Black and brown
Comfort meets contouring when it comes to these boots. While the boots are high, the block heel will help in walking around. It comes in a wider size to fit with your jeans and thicker socks.
Partnerships editor Lauren Witonsky is a fan of any Naturalizer pair. "These are by far the most comfortable high-heel boots I’ve ever worn. The chunky heel really helps, and they also run a bit big so I wear cushy socks to add even more padding," she says.
Vince Camuto Sangeti Boot
- Leg opening is wider
- Tend to crease easily
- Tight around arch
Sizes: 5-12 | Heel height: 3 inches | Colors: 3
With a leather-looking construction and squared toe box, these boots are made for events, work and errands. It encompasses the edge and comfort meant for city dwellers.
Social media editor Daniella Mussachio loved this pair right out of the box. "This is my first pair of tall boots, and it’s safe to say that they have earned a permanent spot in my shoe collection. I love how the wide-calf boot doesn’t suffocate my legs, and the block heel allows for easy walking," says Mussachio.
Thursday Boot Co. Tempest
- Size inclusive
- Easy to slip on
- Tend to slouch down
- Not suitable for longer walks
Sizes: 5-11 | Heel height: 2.5 inches | Colors: 4
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 that won't roll down.
The Lycra-lining interior will keep you dry as it works as a sweat-free feature and it comes with shock-absorbing insoles to withstand longer walks.
Tecovas The Abby
- Leather stretches overtime
- Fits great over jeans
- Shaft doesn't slouch
- They're an investment
Sizes: 5-12 | Heel height: 2 inches | Colors: 5
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 and start stretching out after may wears and tears. Recently, I wore these to a rodeo and my feet did not hurt after 10 hours on my feet.
It's made from a bovine material and the butterfly stitch pattern adds an elegant flair to the design. Tecovas also offers inclusive sizes from 5 to 12.
Overland Major Shearling-Lined Waterproof Leather Boots
- Can be worn below 0°F
- They have a waterproof construction
- Maintenance can be tricky
Sizes: 5-11 | Heel height: 2.5 inches | Colors: Black and tan
For ultimate functionality, choose these waterproof boots made with a Merino shearling lining that will keep you ultra warm. Not only does it have a feminine silhouette, but the comfortable construction and interior can help you withstand temperatures up to -13°F.
It's the perfect winter boot if you live in a colder environment with slush and puddles. I personally wore this pair on a trip to Utah where the temperature was below 0°F.
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.”
Frequently asked questions about knee-high boots
How we chose the best knee-high boots
Our knee-high boots recommendations are based on expert insight and customers' reviews. We selected the best styles based on price, demand and trends currently recommended by the stylists and experts.
Meet the experts
- Jacquie Trevizo is a wardrobe and celebrity stylist who specializes in editorial, red carpet and advertising.
- Gianna Nucci is a Maryland-based fashion stylist who offers wardrobe consulting and custom clothing.
- Dr. Buck Smith is a board-certified orthopedic surgeon who focuses on minimally invasive treatments, joint replacements and joint arthroscopy. He has also worked with professional athletes.
- Dr. Pedram A. Hendizadeh is a podiatric surgeon and founder of Advanced Footcare, a company focused on the care of foot ailments.
