I know, I know … in the grand scheme of life, if you like them, wear them. If you don’t, don’t. But, back to reality — many women are left scratching their heads wondering Am I just too old to wear these? I don’t want to look foolish!

The reality is that when it comes to who wears over-the-knee (OTK) boots best, it really has much more to do with body shape and overall styling than it does with age.

Here are women from their 20s through 50s all wearing OTK boots! Image: The Middle Page

The reason OTK boots look so tempting when you see them on models is that more often than not, models have the right proportions to wear over-the-knee boots well as their legs are usually lean and proportionally long for their bodies. This means that they don’t have to style their way into proportions that work with these boots. But, for the rest of us, wearing these boots can be tricky.

We caught up with Rebecca Thompson, a professional stylist based in Nashville, TN, to get some quick tips on wearing over-the-knee boots.

“I’m short and don’t have long lean limbs which means I could NEVER wear the look! If you have proportionally longer legs and lean limbs, you can wear this look well … IF you like the look,” says Rebecca. “I suggest never wearing a trend just because it’s a trend. I’ve seen 20-year-olds look great in over-the-knee boots and some 50-year-olds who look way better than the younger ones.

“For the over-40 bunch, the look is usually best with thick leggings and a longer top. A woman would have to exude a self-confidence that few of us have to wear the trend with a dress as the dress should fall higher on the thigh than the top of the boot, as in a few inches higher. And, rompers with these boots? While there are ALWAYS exceptions, it’s a look that is hard for most to pull off, no matter the proportion and leanness of your limbs!”

Megan LaRussa, a Birmingham-based style coach who works with clients throughout the country, has some excellent points as well. “Over-the-knee boots can be such a thrilling way to exude femininity, confidence and an all-around modern vibe. The No. 1 rule when rocking this look at any age is to go for a flat to 2-inch heel height to ensure you look more chic and less Pretty Woman. Also remember to never fold down the boot, which can quickly become a pirate-esque look.

“The No. 2 rule when sporting an OTK boot is all about the right garments to pair with this winter must-have. The best choice for every age is a pair of pure indigo, dark wash or black skinny jeans. Complete your ensemble with a well-draped tee and tailored blazer, a cozy v-neck sweater or even a silk long-sleeve blouse with a fur or faux-fur vest over it. These are easy to emulate outfit formulas sure to keep you looking and feeling your best whether you’re 20 or 70!

“The third rule of wearing these fun-loving boots pertains to body type. If you are on the more petite side, opt for a knee-high stretch boot that gives you the OTK look without becoming a thigh high. Try pairing this boot style with a sweater dress for a fabulous day-to-night look, just remember to have an inch or two of skin showing to avoid looking overpowered by fabric. For my curvier femmes, look for this style boot in a calf width that best fits you, preferably with stretch panels for an always comfy and chic look!”

This kitten-heel OTK boot looks great! You don’t need to be a teenager to rock this look. Image: styleatacertainage.tumblr.com
No matter if you are 20 or 75, this look is fabulous! Image: princessesblog76.blogspot.com
Over-the-knee boots can look great, no matter your age! Image: Pinterest

So, there you have it. You can wear the boots if you love the look and style them right, but it’s way easier if you have the right proportions.

For more stylish tips, check out Rebecca Thompson’s website here and be sure to sign up for Megan LaRussa’s newletter here. When you sign up for Megan’s newsletter, you’ll also get Megan’s “25 Expert Style Tips” as a bonus!

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About the Author
Liza Graves

As CEO of StyleBlueprint, Liza also regularly writes for SB. Most of her writing is now found in the recipe archives as cooking is her stress relief!