How to Style Over the Knee Boots

If I had to pick my favorite style of shoes for the winter, I wouldn’t even think twice before blurting out “Over the knee boots!”. OTK boots can take any outfit from casual to glam instantly. They are a current fashion favorite for many, so you can find them in pretty much any style at this point – stiletto, flat, chunky heel, you name it. I also think they are super versatile. So today, I will be sharing my favorite ways to style these boots.

I have three go-to looks when it comes to OTK boots and hopefully, there’s something here for everyone today. These looks can be re-created for date night, girl’s night out, a special event, and many others. As I mentioned earlier, these boots come in so many varieties at this point, there’s something out there for everyone.

Wear Them With Jeans:

Let’s start with the simplest look – OTK boots over skinny jeans. This is probably the easiest to re-create and also can be the most creative since jeans come in many colors. Black OTK boots over white skinnies is definitely one of my favorite looks.

The way I styled the boots in this look was with these dark wash jeans from Express and this black leopard sleeved sweater from Venus. The boots themselves can be found here and are probably my favorite purchase of 2017. The key here is the fit of the jeans. I want to emphasize the word skinny because you want the jeans to hug your legs since the boots will be doing the same thing. If you have any kind of flare to the jeans, they will awkwardly stick out of the boots and trust me, it won’t look cute. So, repeat after me – skinny jeans.


If you own taupe or gray colored OTK boots, mixing them up with purple or green skinny jeans would make for a great look as well and will put a more creative spin on the outfit. Red jeans are also great for black OTK boots and will definitely get you noticed across the room.

Wear Them With Leggings:

This one can get a bit tricky because you can’t wear any kind of athletic leggings unless your boots are flat. If your boots have a heel, stick to leggings that are either leather or have a design that doesn’t make them look athletic. I don’t recommend plain black leggings for black OTK boots because they can blend together and you lose the whole effect from the boots but if your boots are any other color, plain black leggings are fair game.

The way I styled my boots in this look was with a long plaid tunic that is split on the sides and these leggings with mesh insert sides. Some other leggings that would look amazing paired up with high heeled OTK boots would be these ones with side lace ups and these with mesh sections. Can you tell that I really like leggings from Express?


Long sweaters are another great option for this as the goal is to cover your tuchus, be warm but still look cute so a look I’d recommend is a warm red tunic sweater, leather leggings and OTK boots for a going out look for this frigid winter we’re having.

Wear Them With A Dress:

Now my favorite way to wear OTK boots – with a dress. Preferably one that sits tight around the middle of your thigh so that you can show off the boots. Don’t go much higher 😊

In this look I wore a bodycon off shoulder sweater dress (one that failed to keep me warm, surprise!) with brown OTK boots that you can find here. These boots don’t look as good with jeans or leggings so I’ve pretty much reserved them for dresses only at this point. With that color, they’re great for black, olive, and green dresses and I’m excited to find more use for these beauties.

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There you have it for my recommendations of styling OTK boots. If you follow me on Instagram, you already know that I’m a fan and this post was no surprise. I hope you guys found this informative and I hope I was able to provide some outfit inspiration. As always, thank you for reading and don’t forget to follow me on InstagramPinterest and like my Facebook page!

*I get commission for purchases or clicks made through links in this post.

41 Comments Add yours

    1. Thank you! I might have to save it for the spring since the temps right now are too frigid!


  1. The 3rd look is so freaking stunning! I love how you styled all of these though, so fashion-forward!

    Liked by 3 people

    1. Thanks, girl! The third look definitely seems to be the most popular! 🙂

      Liked by 1 person

  2. I absolutely love that dress + boot combo, it looks amazing on you! Thanks so much for sharing! xo

    Liked by 2 people

    1. Thanks for reading! That was my favorite look to shoot – at least for the moments that I was able to ignore the 30 degree weather haha

      Liked by 1 person

      1. Ahhhhh I know. This weather has been brutally cold lately.


  3. ughmango says:

    I love love love the third look! So gorgeous! I don’t own OTK boots (yet at least hehe) but I am for sure really tempted to buy them as there are so many ways to style them! xx

    Liked by 2 people

    1. Thank you! You should definitely get a pair! I think they’re such a staple! 😊


  4. Siyana says:

    The last look is so stunning! x

    Liked by 2 people

    1. Thank you! That seems to be the favorite by far!


  5. Fashion By Deborah says:

    I really like how you styled them! ❤

    Liked by 2 people

    1. Thank you so much!

      Liked by 1 person

  6. Beyoutiful says:

    Love the 3rd outfit, you look lovely!

    Liked by 2 people

    1. Thank you so much! So sweet!

      Liked by 1 person

  7. Sarah says:

    I love how they look with jeans! 🙂

    Liked by 2 people

    1. Thank you! It’s probably the most common way I wear them!

      Liked by 1 person

  8. What I love about this post is that you showed hoe high knee boots are so versatile!!

    Liked by 2 people

    1. Thank you so much! There are really so many ways to wear them!

      Liked by 1 person

  9. thebellestyle says:

    I love OTK boots too!! 😀 Btw, you rock in the third look ♥


    Liked by 2 people

  10. pepitadaria says:

    Love your outfit with the dress 😍😍

    Liked by 1 person

  11. Saffy Muna says:

    Oh I love this style I can’t wait to try some!

    Liked by 1 person

  12. byrdofpassage says:

    These looks were super cute!! I love over the knee boots so much!

    xx Birdie

    Liked by 2 people

    1. Thank you for reading! 🙂

      Liked by 1 person

  13. yes those are all so super cute! check out my article on leggings as well:

    Liked by 1 person

  14. Love me some over the knee boots 👢

    Liked by 3 people

    1. Me too, girl! 🙂


  15. My fave type of boots!! Love this style guide!

    Liked by 2 people

    1. Thank you so much! 🙂 Definitely my favorite type as well!


  16. xtina says:

    love your style!

    Liked by 2 people

  17. Iriowen says:

    First look! 😙


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