Cute Over the Knee Boots Outfits for 2023

Are you wondering how to wear over the knee boots? This guide will teach you all you need to know.

Shop Over the Knee Boots: Here, here, & here

My absolute favorite purchase as of late are these black suede over the knee boots! Not only are they adorable, but they are actually comfortable, and they keep your legs warm. You can dress these boots up or down depending on how you style them.

I have had a lot of people ask me how to wear over the knee boots, so I wanted to dedicate a blog post to answer that question. If you don’t style OTK boots correctly, they can definitely look a little risqué. BUT, I am going to show you 5 ways to wear them with casual outfits and fancier outfits.

5 Ways to Wear Over the Knee Boots

Look #1: Jeans & Boots

I love that these boots are flexible and comfortable enough to wear over jeans.

I paired my gray moto jeans with these boots because I liked the contrast of color with my gray jeans and the rest of my black outfit. Any pair of jeans would look great with these OTK boots. Believe it or not, white jeans with these black boots looks amazing. Wearing these boots with white jeans would be a great way to transition these OTK’s into your spring wardrobe.

Since the boots are on the fancy side and the jeans are not, I wanted to dress up the look with a black shirt and fur vest. If you do not have a fur vest in your closet, a sweater with colored jeans or black jeans would also look great with the boots.

You can truly pair these boots with any casual look. These boots would look great with jeans and a flannel. Don’t be afraid to throw these boots on with a casual outfit to give it a little more edge.

Look #2: Skirt & Boots

I picked up this blouse and skirt from Free People that pairs perfectly with the OTK boots. I love the 70s vibe of this outfit. You could recreate this look with any a-line mini skirt and blouse that you already own in your wardrobe. How cute would these boots look with a patterned skirt and chunky sweater?! The outfit options are truly endless with these boots…that is why they are a wardrobe must have!

Look #3: Cotton Dress & Boots

This is my favorite look out of all 5.

This dress is from Express (under $50!!), and I love the way it looks with the boots. I paired it with a hat and scarf which made it have a more casual feel. This would be a great outfit to wear on a date in the fall or winter!

You can take this look from day to night, too. Wear it as pictured during the day, and at night take off the hat and scarf and add a statement necklace and a clutch…like I said, it’s the perfect date outfit from day to night!

Look #4: Sweater Dress & Boots

This is the coziest dress for the wintertime, and I love wearing it with the OTK boots. When it is freezing cold outside, it’s nice to have tall boots that keep your legs warmer than if you were wearing heels or booties. Any sweater dress would look adorable with these boots.

Look #5: Fancy Dress & Boots

One of the many reasons I love these boots is because they are dressy enough to pair with a nice dress. If you have a fancy event that you are attending in the winter, these boots will be perfect for you. You will be much warmer than the women who wear heels with their dresses!

I am always freezing, so it’s nice to be able to wear tall boots with dresses instead of having your legs exposed to the cold.

OTK Boots Styling Tip

Play with proportions. When you are picking out an outfit to wear with your OTK boots, it is important to think about the length and fit of your clothes. If you want to wear a bodycon mini dress with your boots, it will definitely give you a certain type of look that you may not be going for. It is okay to wear a short dress or skirt with these boots, but try adding a knit sweater or army jacket on top. It’s all about proportions and fit when it comes to creating a stylish outfit with OTK boots. Fun fact: The Stuart Weitzman OTK boots were actually inspired by Julia Robert’s character in Pretty Woman…this is why it is important to be mindful when styling an outfit with your boots 😉

I showed you 5 ways I would style my OTK boots, but I also want to show you how other bloggers styled their boots in a way that I love.

I absolutely love this outfit because it shows that you can wear a short dress with OTK boots without looking too street corner-y if you know what I mean…She achieves this by adding layers over the dress and by accessorizing. This is making want to buy a blanket poncho ASAP! Thanks for the inspiration, Lene!


This look is absolutely timeless and that is what I love about it. Wearing a LBD with over the knee boots and throwing on a wool coat is so classy and beautiful. She absolutely nailed this look! Her dress, coat, boots, and handbags are all pieces that will never go out of style, so they are worth the investment.


This is another look that I am obsessed with. I love that she is wearing jeans shorts with her boots! This is such a cute outfit to wear on a fall day when it’s not too hot yet not too cold. Don’t be afraid to wear your boots with shorts! The boots look just as cute with dressier shorts as they do with these casual cut offs.

Which outfit is your favorite?

Leave me a comment down below and let me know which one you would wear.

I hope this guide helped you learn more about how to wear over the knee boots. Thanks for reading!

8 thoughts on “Cute Over the Knee Boots Outfits for 2023”

    • Hi Mia, thanks for your comment! I have worn them in colder weather than that at night so I think you will be fine in 55 degree weather! Let me know if you have any other questions! xo, Kimmie

  1. I like lene’s look I think the tan OTK boot goes perfect with her skin tone I like the idea of the scarf or poncho the tan color give her a light silhouette


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.