14 tall boots to wear this winter and how to style them

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

While this style of shoe has been spotted on many celebrities and off the runway since early fall, knee-high boots are a cold-weather staple thanks to its effortless functionality and sleekness. Not only can they elevate any ensemble, they also elongate your legs – which is always a plus!

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

How to choose the right tall boots

One of the first steps to consider before investing in new winter boots is to think about your surroundings. 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.”

Second, think about your daily lifestyle and the type of shoes you want to match your wardrobe. “Maybe you walk a lot on your commute, so you would need a more durable and comfortable style,” Nucci added.

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

If your city has mud and puddles to overcome this season, Nucci says there are “a lot of pretty winter boots that aren’t functional for rain and snow, so you want to be sure that you’re not just buying aesthetics.” For example, although leather boots are stylish, they 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 Tall Boots

For the day

Both designers 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 loose trucker jacket. “For New York weather in March, [add] a long quilted coat layered over that oversized trucker jacket, throw on a nice hat and you’re done.”

One of Nucci’s favorite casual daytime outfits to pair with knee-high boots is “pair them with leggings, a faux leather or heavyweight ponte-knit fabric, and a chunky sweater. For a more elevated look, wear Pair them with skinny jeans, so they slide in better, and a structured jacket like a blazer layered over a fine knit.”

For the night

For the evening, Nucci likes to wear a 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 stiletto or a stiletto heel, a heel always makes an outfit dressier.”

As for Trevizo, a monochrome black look will complete your evening outfit. “Whether it’s a bodysuit or a little black dress with your thigh-high boots, [this will look more provocative]. Go all out and opt for an oversized blazer or faux leather jacket for LA weather or choose a long trench coat or faux fur coat if you’re in New York.”

What styles of boots 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 small heel.

Additionally, there’s greater interest in a lugged-sole trend that “will continue through 2022, as well as form-fitting styles that [really] squeeze the calf,” Nucci said. Other trends that continue to dominate street style are Western-inspired boots and over-the-knee designs.

Here are the most stylish tall boots for winter, selected based on recommendations from our experts, so you’ll make a statement with every stride.

The best knee-high boots, based on expert reviews

Universal Thread Lainee Scrunch Heel Boots

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

Marc Fisher Renn Thigh High Boots

If you’re looking for some extra coverage, opt for these over-the-knee boots from Marc Fisher. This style won’t sag and hug your legs all the way, and the small block heel makes it easy to navigate. Plus, according to Macy’s shoppers, these fit great even if you have skinny legs.

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

For a bolder vibe, consider these boots that reflect ’80s style. The bigger the better when it comes to combat boots, especially when that style is reminiscent of Dr. Martens.

Journee Collection Vellia Knee High Boots

This low-heeled boot won’t wear you out when you’re strolling around town. It is available in four different colors to dress day or night. Plus, this will be a great pair to transition into spring.

Asos Carla chunky flat ankle boots

Avoid muddy sidewalks with these chunky, lug-soled boots. This boot trend continues to rule street style and is the perfect addition to your casual winter wear, especially if your city is covered in snow.

Journee Collection Thérèse wide calf boot

This western-inspired boot comes in three flattering shades, including one of the hottest colors of 2021. The boots feature a deep V detail to the brim, pointed toe and are equipped with Tru Comfort Foam insoles for a more comfortable walk.

Dune Tawn Faux Sheepskin Trim Knee High Boots

For days when you need protection and style, opt for these leather boots with shearling details. The pair has a two inch high heel for comfortable walking and a zip fastening.

Boston Proper suede thigh-high boots

With dozens of five-star ratings, this pair from Boston Proper is your go-to style for everyday wear. Pair them with 2000-inspired trends like low-rise jeans or a tulle skirt for a maximalist look. “I wore them to a party with lots of standing around without any discomfort,” one reviewer shared of how convenient they are to wear.

Sam Edelman Larina Waterproof Knee High Platform Boots

Keep your feet dry in these waterproof high boots from Sam Edelman. Available in four versatile colors, they’re made with a synthetic leather upper lining that won’t rip and keep your legs comfortable. “They kept my feet warm and dry in the snowy Dillon, Colorado,” shared a Dillard shopper.

Looks like summer Trinity knee high boots

These boots combine comfort and style while keeping your legs warm during the winter. The style features lace-up details at the back and a rubber sole for confident walking in the snow.

Nine West Hiya Heeled Boots

Fight your way through the icy atmosphere with these stylish boots from Nine West. The pair comes in four neutral colorways with a Western-inspired pointed toe. Wear it with a sweater dress and a trench coat for a refined look.

Thursday Boot Co. Storm

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

Boots Dolce Vita Solei Nubuck Whiskey

Unleash your inner cowgirl with these western-inspired boots. They come in three neutral colors and feature a manageable two-inch heel for easier strides. PS customers have noted its perfect fit, so size up if you need to.

Overland Major Sheepskin-Lined Waterproof Suede Boots

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

Chiara Ferragni Hearts ankle boots

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

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