Knee-High Boots Are Back — Don't Make These Fashion Mistakes

After a few years of ankle boot domination, knee-high boots are seemingly everywhere. 

“We’ve been seeing a small reemergence of this trend for a couple of seasons now, and it kind of feels like we’re at a moment in time where everyone’s onboard and adopting them and looking for different iterations of the tall boot that works for them,” said Candace Read, a wardrobe stylist based in Ohio.

Knee-high boots were huge back in 2015 and 2016, but fashion looks really different now than it did then.

“We’re definitely seeing much more volume [in clothing] which is a big departure from how we were seeing it previously, with leggings and slimmer pants and skinny jeans and all of that good stuff,” added Read.

So how should you be styling your knee-high boots now? Below, stylists share the dos and don’ts for styling knee-high boots.

Don’t wear a boot that’s disproportionate to your body.

“I think one of the biggest mistakes, honestly, is the right selection of boot ... it’s not always proportionate to the individual,” Read shared.

In general, you want your knee-high boots to end just under your knee, according to Ashlyn Greer, the founder of Fashivly, an online personal styling service. Boots ending at the kneecap tend to be hard to walk in, Greer noted. Additionally, you want to make sure the shaft of the boot isn’t too loose around your calf, or too tight. Not only can this throw off your look, but it could lead to discomfort, too.

For example, a shorter person shouldn’t wear a knee-high boot that hits them too high, or someone with thin legs shouldn’t pick a boot in which their calves are swimming (a tapered boot or a boot with a zipper or elastic could be ideal in this case), Read noted.

Greer said many of her clients are frustrated by limited options for larger calf sizes, but know that things are getting better. “There are some really great brands like Dolce Vita and Vince Camuto that are finally coming out with really great boots in both wide calf options and extra wide calf, which is great,” stated Greer. 

It may take a few tries to find the boots that are best for you, and that is OK.

“If you want to adopt the trend, then it’s worth it to invest that time to find the right one ... that way, it can last in your wardrobe for seasons to come,” Read said.

Don’t eliminate the possibility of knee-high boots just because you’re short.

“You can wear the knee-high boots no matter your height,” Kayla DelSanto Westwood, a stylist at Nordstrom, told HuffPost.

“Often, when I am styling clients, my petite customers feel they can’t wear a knee-high boot or even over-the-knee [boot], but I completely disagree,” Westwood stated, adding that many brands offer knee-high boots with shorter shaft lengths, which allows shorter folks to wear the style.

The average shaft height of a knee-high boot ranges from about 13.75 inches to 17.75 inches, according to the Stuart Weitzman website, which is a pretty big range. For a shorter person, it’s a good idea to purchase knee-highs closer to that 13.75-inch length.

Don’t limit yourself to tucking skinny jeans into knee-high boots.

According to Greer, one of the toughest things for folks when it comes to knee-high boots is deciphering how to style them with pants.

“It’s a little bit trickier because a lot of us have pushed those skinny jeans toward the back of our closet,” Greer noted, and skinny jeans were many people’s go-to when styling knee-high boots back in 2015 or 2016.

Now, with looser pant styles such as flares and wide-legged jeans in fashion, it’s not as easy to style knee-high boots.

“It’s really all about proportions [you can try] something that’s got a little bit more of a straight leg or even a baggier jean, so you have some of that puddling if you are tucking in the pants,” said Greer, “but, this is tough, I’m going to be honest. It’s kind of an art and not a science and you’ve really got to balance out the proportions of the full look and make sure that you’re pairing it with the right boots.”

There may be some trial and error — meaning it’s a good idea to try on some outfits before you have to run out for an event.

“So, a couple of tips: Opposites really do attract with this type of pairing. If you’re doing that flat buckle moto boot that has a lot of ... visual weight, pairing that with skirts and dresses or leggings [or a] a slimmer pant is going to be your best option,” Greer said.

“If you’ve got something that’s a slim, pointed-toe knee-high boot, that’s the right silhouette to experiment with tucking in a fabric that’s got a little bit more to it like a straight or a baggy jean,” she added.

And, if all else fails, leggings remain a good option, she noted.

Don’t always think you have to tuck your pants into your boots.

You may think that your pants should always be tucked into your knee-high boots, but that isn’t true, both Read and Greer said.

“We are wearing looser fitting pants and looser fitting skirts, a lot more volume than what we were wearing in 2015, 2016,” said Read. “I think it’s been really fun to style your knee-high boot under a really full leg trouser, which some people might say that’s a little counterintuitive because you’re missing the shaft of the boot, essentially, but knowing that it can be layered under a wide leg trouser, I think is great, and we’re seeing that a lot.”

“A knee-high boot is such a workhorse of our closet, instead of before where we had to have an ankle boot and a knee-high boot. Just get the knee-high boot, wear that with your skirts and dresses and then just wear your pants over the boot,” Greer added.

Wearing your pants over your knee-highs looks good when you’re walking or sitting, Greer said, and adds a different, taller silhouette under your pant leg.

Leaving your pants untucked is particularly good with flares, bootcut jeans, baggy jeans, cropped wide-leg jeans and even straight-leg jeans that are wide enough around the ankle and calf, noted Greer.

Don’t limit your boot-wearing to the cold-weather months.

Wearing boots in the fall and winter is a no-brainer, but Westwood said you shouldn’t limit this shoe choice to just those seasons.

“Get rid of the thinking that knee-high boots are only seasonally appropriate ... it’s all about how you complete your look and style it out,” Westwood said.

In other words, go ahead and wear your knee-high boots in the spring and even summer — and don’t be afraid to show some skin, Kyla Flax, the head of styling at Anthropologie, told Huffost.

When it’s warm, Westwood recommends “pairing [your boots] with tailored shorts, crisp tailored shirt options, oversized blazer and jewelry. I especially love the layered jewelry look here.”

You can even pair your boots with some leather shorts, said Read.

Throughout the spring and summer, don’t focus on covering up while wearing boots. 

When all else fails, remember that skirts and dresses go extremely well with knee-high boots.

“I think everybody knows a great, easy outfit to wear with [knee-high boots] is any skirt or dress — it can really be any length,” Greer said. 

Read said long maxi skirts are in right now and look just as good with this shoe choice as a pair of black tights and a black mini-skirt. 

Flax said she likes to style knife-point boots with a slip dress — “it’s easy to throw a jacket or heavy sweater on top of your look to make it feel more work appropriate.”

When wearing your boots, don’t forget to keep your personal style in mind.

From motorcycle and cowboy to heeled and flat, there are endless styles of knee-high boots out there. And beyond that, with jeans, skirts, billowy pants, dresses and more, there are endless styling options, too.

It may feel overwhelming, but in the end, select a style that you’re excited to wear.

“When choosing a boot, I’d urge shoppers to go with their own style. If you are a classic minimalist but are interested in cowboy boots, wear them with jeans and a blazer,” said Flax, “Stay true to your own aesthetic when incorporating new pieces.”

Additionally, it’s important to think about your lifestyle, too, noted Greer.

“Are you commuting? Maybe the moto boot is a better option for you. Are you somebody that loves to play with more feminine silhouettes? That kitten heel pointed-toe boot’s probably more right for you,” stated Greer.

All in all, have fun with it — pick a style that’s right for you, that you’ll look forward to wearing and that you can pair with lots of items in your closet.

Looking for some new comfy boots? Take a look at this reviewer-beloved selection below.

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