You are not sure about Over The Knee (OTK) boots? Well, I wasn’t either until I tried them.

This post was originally published in January 2022 and updated January 2023.

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I have been eyeing this style of boots for years. Watching other women rock them from afar. I tried a pair last year without a heel. Those were a good start. This season I wanted to get a bit more adventurous. I’m so glad I did.  Alright, here is how I wear OTK boots!

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Get a Pair of Over The Knee Boots with a Heel

First, I think getting a pair with heels helps. Let me explain why. It gives the boots more structure. It also avoids the “I am a pirate” look. You are not going for that look.  Also, it gave me more options in terms of items to wear them. I could do a dress or jeans and both worked. 

Make Sure They Can Stay Up

Second, the whole point of these boots is for them to be able to stay up over your knee. So, be sure to find a pair that does that (and does it well!).  My over the knee boots had some stretch in them. Look for a pair that has that and will fit your legs. That way they stay up and you don’t have to keep messing with them.   


The over-the-knee boot trend shows zero signs of slowing down. We’ve embraced their over-the-top nature..

Source: Harpers Bazaar

Have Fun Wearing Them

Lastly, fully enjoy this pair of boots! That means trying different colors as I did. I stayed away from black. That let my boots standout a bit more. Also, try them with a shorter hemline. This allows a bit of skin to show. Likewise, the shorter hemline paired with the over the knee boots results in a balanced pairing visually. 

Want other outfit ideas? Check out other posts here and here.

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