black tweed dress outfit

An Over the Knee Boots Outfit To Inspire Your Cold Weather Dressing

We may earn money or products from the companies mentioned in this post.

It’s not cold weather season until you break out some boots! Come fall and winter, you have your pick of boot styles from a vast sea of options. From ankle boots to thigh-high boots, elevating your outfit is just a boot away. Here’s one of my favorite over the knee boots outfit to inspire your fall and winter dressing this season!

boots | hat (similar) | dress

Over the knee boots, also called otk boots and sometimes thigh-high boots, joined fashion circulation once designer Balenciaga showcased a pair of boots that went past the knee in their 1960’s fall runway show. They peaked in popularity in the ’80s, being worn by supermodels and famous singers like Cher. After dying down for a little, they had a resurgence once celebrities like the Kardashians started wearing them several years ago.

Thigh-high boots are sometimes considered fashion’s “kinkiest” boot, which became even more true once the Kardashians got their hands (er, feet) on them. And well, just like the slip dress, I say it’s all on how you style it.

So, where does that leave the boots now? You may be wondering, “Are these still in fashion?”

Short answer? No.

If you’re wondering why I’m even doing a post on them, then I’ve got to give you the long answer…

The Difference Between Fashion and Style

Otk boots are not classic like knee-high boots, which will always be in style but maybe not in fashion.

Meaning, what’s “in” is constantly changing, and thanks to social media and influencers, it doesn’t take long for a new fashion to really gain traction and become popular. So what’s in fashion (what’s hot), is always changing and comes and goes. Fashion is what’s popular at that time.

But what’s in style doesn’t come and go. Because it’s you.

“Style” is a shorthand term for “personal style”. Style is a combination of looks that lasts many seasons (for example, tall boots and striped sweaters will always be in style).

Style is also innate. It’s a personal expression of how you dress. Style is mixing and matching pieces together (some classic and maybe even some trendy), creating a look that speaks to who you are.

Being “fashionable” is easy. Just wear whatever the latest trend is! Style takes more work because you are cultivating your own unique outfit and persona.

What you see on the runways or in Vogue is what’s in fashion. What you do with those clothes and accessories in your day-to-day life is your style.

So, all of that to say. Are over the knee boots “in” right now? I’d say no, they’re not in fashion right now in fall 2021. Boot trends are always changing and lug soles have taken over the boot scene!

Does this mean you should stop wearing them? If you want to be fashionable, pick up a pair of chunky soles instead.

But if it fits into your personal style, then wear away!

I like the look of these boots and they fit my personal style. So I will continue to wear them, whether they’re in or not because I like them!

You too? Okay, so let’s get into the outfit idea then!

Even though these boots are typically thought of as kinky or risque, I think you can style them in a chic way- as I did! There are a few key tricks to making that happen:

  • Pick a solid, neutral boot color instead of a bold color or print like reptile skin.
  • Choose no heel or a block heel instead of a sky-high stiletto.
  • Pair with tights or leggings if you are wearing a shorter hemline.
  • Choose a looser-fitting top or dress instead of a bodycon dress.
  • Keep the rest of your look classic by wearing things like a camel coat or pearls.

Can any body type wear them?

I think yes. Though if you find that you have more muscular thighs, you may have to kiss from frogs before you find the pair that doesn’t squeeze the life out of you.

Alternatively, if you have slimmer than average thighs, you may have to try on a few different pairs before you find the ones that don’t slide down all day.

Related: These Are the Best Boots For Women With Skinny Legs

Benefits of over the knee boots:

  • They can make you look like you have long legs!
  • Since this style of boots is so tall, you can usually get away with wearing short dresses or short skirts (like a mini skirt) without exposing more skin than what you’re comfortable with.
  • Whether you go for a flat sole or a high heel, they can work for both a casual look and a dressier occasion.

If you think you’ll be wearing these boots around in your day-to-day life, opt for no heel so you are more comfortable. If you want to dress these up and plan on wearing them to holiday gatherings or family photos, go with a pair that has block heels. Though I’d avoid wearing them to an event like a cocktail party.

Related: Affordable Yet Elegant Dresses to Wear to a Christmas Party

Black boots are always a good idea. Brown comes in a close second. Since the length of these is already a statement, I’d try to avoid purchasing one in a bright color to keep a classic element.

For a casual outfit and trendy look, you can try “lampshading”. Lampshading in fashion is when you pair otk boots with an oversized knit sweater, shirt, or dress. When the top of the boot barely grazes the bottom of your top, it’s supposed to create a lampshade effect.

Some over the knee boots outfit ideas to get you started:

otk boots + short dress + long coat

otk boots + sweater dress

otk boots + high waisted plaid skirt + long sleeves

otk boots + oversized sweater

A fun way to wear this style is with a short hemline, but you can wear them over jeans too for everyday wear. Another one of my favorite ways to wear this knee boot style is with leather leggings, as you’ll see in this Thanksgiving outfit ideas post!

These typically won’t be a boot style that you’ll wear in the warmer season. You can break out some taupe ankle suede boots instead for your fall to spring outfit transitioning.

For even more outfit ideas, check out the pictures below!

Over the knee boots outfit ideas
over the knee boots outfit

For other cute outfits you can wear this fall and winter, keep reading!

Up Next:

5 Blazers To Wear With Jeans for an Easy Yet Put Together Outfit

How To Wear a Sweater Over a Dress Shirt in a Chic and Classic Way


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.