When over the knee boots started popping up everywhere I had a love hate relationship with it – mostly I tried to figure out how to wear thigh high boots without looking trashy! There were so many cute outfits that I wanted to try out immediately and then there were some “questionable” outfits. 😉 My mama taught me to dress more conservatively (also, I wish I lived in the south where women are ladies ha!) so when I picked up my first pair of thigh high boots (and then my 2nd and 3rd!) I realized it’s actually super easy to wear them and look classy, not trashy. 🙂
Let’s dive right in to some clothes to wear with thigh high boots!
How to Wear Thigh High Boots (without looking trashy)
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Black Dress + Jacket
Let’s start with some dresses to wear with thigh high boots. I love the look of this outfit because it’s one you can wear to work or professional settings without feeling too “much”.
The sherpa style jacket tones down the fitted dress and otk boots and makes it work appropriate.
With a Casual Dress
I love wearing thigh high boots with casual dresses! This dress hits just below the top of the boots so there’s not even any skin showing (also perfect for super cold days!).
The boots dress up the casualness of the dress a bit which makes this outfit work appropriate as well.
Midi Skirt + Graphic Tee
This is one of my newest (and favorite) ways to wear over the knee boots! I love midi skirts but when the weather gets cold it can be hard to wear them. Pairing them with otk boots is a perfect option!
I’m also LOVING this graphic tee that says “friends over follower”. Preach!
Dark Denim + Mock Turtleneck Fitted Top
I actually rarely wear fitted tops but I love this one! The embroidery gives it a feminine feel and the mock turtleneck keeps it conservative.
I also feel like this outfit makes my legs look incredibly long when in fact, they’re not! (Girls that are 5’3″ rarely have long legs ha!)
With Black Skinny Jeans + Chambray Top
My favorite way is with black skinny jeans and really any kind of top. Black denim helps you look a bit nicer than regular denim which can make it be more appropriate for work. You could also substitute denim for leggings if you have a long enough top and thick enough leggings. 😉
Chambray is classic and pretty much everyone has on in their closet! It’s also super easy to style in a variety of ways. You can tuck it all in, knot the bottom or do a half tuck!
If you’re looking for ways to dress down thigh high boots, chambray (or a sweater below) are some ways to do just that!
This is one of my favorite outfits. I love the layers of pink with the darkness of my jeans peeking out. And let’s be real, you’ll look far from trashy if you have a bunch of layers on! 😉
With Jeans + A Sweater
Probably the easiest way to wear thigh high boots without looking trashy is with jeans and a sweater! You’ll feel (and look!) more chic in over the knee boots when you’re wearing a chunky sweater. I promise this will become a reoccurring outfit in the winter.
I love adding a pop of a fun belt too. Nothing beats a little bit of leopard!
There you have it! I hope this gave you some ideas and inspiration to know how to wear thigh high boots without looking trashy! It’s really not that difficult as you can see!
The boots I wore throughout this post are my absolute favorite boots and worth every single penny! I sized up just a half a size and that was perfect (some say they run big). They’re super comfortable and don’t slide down your thighs causing you to tug them up all the time. They’re amazing!
Thanks so much for reading and following along. Be sure to check out my tips for wearing a white button down shirt multiple ways!