Over The Knee Boots: How and Where to Wear Them

Styling Over The Knee Boots

Welcome to boot camp! Today we’re talking all about over-the-knee boots – from what pants to wear with them, how to style them, and where to wear them. 


Over-the-knee boots are a fun statement piece in any outfit, and there are so many ways to wear them! Today, I’ll explain how to wear over-the-knee boots for different occasions, what pants, skirts, and dresses to wear, what socks to pair them with and so much more. I’ll break down everything you ever wanted to know about over-the-knee boots!


A few great pairs of over the knee boots

I’ve had my over the knee boots for YEARS and they’re Circus by Sam Edelman brand, and they’re still available in a few sizes HERE.

We rounded up a few other similar over the knee boots in flat and heeled styles at all different price points!


What socks I wear with over the knee boots

If you want some boot socks that cover your ankles, THESE ONES are my favorite. If you want super tall ones, I don’t own THESE ONES, but they get great reviews. And if you just want a pair that covers your feet, my favorite low ones are BOMBAS, but THESE MORE AFFORDABLE ONES are fantastic too.


How to store your tall boots

I have THESE BOOT FORMS to keep my boots standing up straight and not losing their shape. I’ve had the same ones for years and I use them for all my boots, but they’re especially helpful for over the knee boots.


Where to wear these boots

  • the office
  • date night
  • church
  • concerts
  • girls nights
  • baby and bridal showers


What kind of bottoms can you wear with tall boots

  • SKINNY JEANS. Since these boots are so fitted all the way up, they’re best with a fitted pair of jeans, not looser. Pair them with skinny jeans for a sleek look. You can do lighter wash, mid wash, or darker wash blue, or white or gray or black. Anything works well, regardless of what color of boot you have.
  • LEGGINGS. If you’re going for a more casual look, pair your over the knee boots with leggings and a longer tunic style sweater.
  • LEATHER LEGGINGS. I love mixing textures, and leather with suede is really good and subtle, especially if they’re both a black color.
  • SKIRTS. I think over the knee boots look best with skirts that are a little shorter, so there’s a gap of leg between the boot and the shoe. But if it’s winter and you need your legs covered, wear a midi or maxi skirt and wear your boots underneath. They’re a good option since they’re fitted at the ankle and won’t make your legs look blocky.
  • DRESSES. Same as the skirts, shorter so there’s a gap looks great, or longer midi or maxi can also look great.

DO NOT wear with wider leg jeans and stuff them into the boots, and DO NOT wear with joggers or other casual pants.


How to balance your outfit with these super tall over the knee boots

With super tall boots like this, you need to pay attention to outfit balance, cause otherwise your outfit can feel a little bottom heavy.

I’d recommend pairing with dresses that are a heavier weight material, like a sweater dress or flannel, or something with a bold color or print. That helps draw attention up, rather than all the focus being on the bottom. I wouldn’t wear these boots with a slinky silk dress, or a light cotton dress or skirt cause the boots would make it feel too bottom heavy. Make sense?

With jeans and leggings, again, choose something that adds a weightiness to the top half of your outfit, like a long, structured blazer, an oversized sweater or tunic or cardigan, a chunky knit sweater, a top with a bold print or color, a scarf, a wool coat. All of these are easy ways to add balance to the outfit.


How to wear them without looking dated

As always, the key to wearing something older without looking dated is to pair it with modern or classic pieces, and make sure they fit well.

Wear with a modern dress, wear with a modern or classic blazer, wear with a classic button up shirt and jeans and a chic belt. Wear with a classic sweater. There are lots of ways to wear them so you don’t look outdated. Also, keeping your hair and makeup modern is a big way to keep your entire look updated. Think of the women who still wear hair and makeup from the 80’s. They can be wearing modern or classic pieces and still look like they walked out of 1986 because of their hair and makeup. So keeping that updated should be high priority!


How these boots should fit

These boots shouldn’t be skin tight, but they should definitely be more fitted, especially at the top of your leg. It can give “Robin Hood Men in Tights” vibes if you’ve got loose boots flapping around above your knee.

Mine have a drawstring on the top to tighten as needed, and that helps them stay in place and adjust to my leg width. Not all do that, so if you choose a pair that doesn’t, make sure they still fit you nicely up at the top of the knee or mid thigh. No squeezing, but definitely make sure they fit well.


Here are some outfit ideas with this tall style of boot!


over the knee boots with plaid dress
over the knee boots and tan sweater
over the knee boots with jeans
over the knee boots with leggings
over the knee boots
Merrick's Art Over the Knee Boots

I hope this is helpful!

If you missed the first two days of BOOTCAMP, check out day one all about Chelsea Boots HERE, and day two all about Neutral Block Heel Ankle Boots HERE, and day three all about knee high boots HERE.



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