7 Classy Over the Knee Boots Outfit Ideas

When over the knee boots started popping up everywhere I had a love hate relationship with it – mostly I tried to figure out some cute thigh high boots outfits!

Over the knee boots are great for layering over jeans or tights or under dresses, skirts or cute jackets. There are tons of different styles of over the knee boots like sock-like silhouettes, suede styles, slouchy looks and more.

Let’s dive right in to some clothes to wear with over the knee thigh high boots!

7 Over the Knee Boots Outfit Ideas

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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.

Dress | Jacket | Boots

With a Casual Dress

I love wearing over the knee 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 thigh high boots dress up the casualness of the dress a bit which makes this outfit work appropriate as well.

{Dress (old) | Boots | Bag }

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!

Skirt (from a local boutique – similar here) | Tee | Boots

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!)

{Denim | Top (sold out)| Boots | Earrings (old, similar here)}

With Black Skinny Jeans + Chambray Top

My favorite over the knee boots outfit idea 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!

{Denim | Top | Boots |  Earrings }

With Layers

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! 😉

{Denim | Top (almost sold out!) | Cardigan | Boots | Earrings }

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!

{Denim | Sweater| Belt (sold out, similar here) |  Boots | Monogram Necklace |Earrings (old, similar here }

There you have it! I hope this gave you some ideas and inspiration to know how to wear thigh high boots and some cute outfits to wear them with! 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!

With love,

Jen