Over-the-knee boots are one of those surprisingly wearable types of fall and winter shoes that never go out of style. I have a couple of thigh high boots in my closet, and even though I’m much more of an ankle booties person at heart, I find myself reaching for my OTKs when I want to make a statement or need a little more height to my shoes to balance an outfit.
If you’re stumped on what to wear with over the knee boots, you’re in the right place. Below are eight over the knee boots outfit ideas for fall and winter, plus a few styling tips to keep in mind as you recreate these OTK looks for yourself.
Over the Knee Boots Outfits
1. With a Sweater Dress
Sweater dresses and thigh high boots are a match made in heaven. The trick is to find a sweater dress in a length that doesn’t compete with the hemline of the boots—don’t be afraid to show a few inches of skin between the two. I’ve styled the same sweater dress with my Stuart Weitzman lowland boots for a casual, flat over the knee boots look and with heeled OTK boots for a slightly dressier take. To carry this outfit into cold weather, play with outerwear in varying lengths (a coat the length of the dress or longer usually feels best).
2. With a Mini Skirt
If you like the idea of mini skirts but think they’re too sexy for your style, try pairing a corduroy or leather mini skirt with an oversized sweater and over-the-knee boots. This is an easy way to minimize the amount of skin shown while still leaning into the playfulness of the skirt. For a casual OTK boots outfit, reach for flat thigh high boots. For a nighttime or date night look, go with a stiletto or block heel.
3. Over Skinny Jeans
The key to styling over the knee boots with jeans is to make sure the jeans are a true skinny jean. This will eliminate any bulk at the knee or calf area, which could counteract the slimming, lengthening effect of the boots. My current favorite jeans to wear with tall boots are by FRAME. They have just the right amount of comfortable stretch while still sucking you in, and they don’t loosen in the wash. This OTK boots outfit is a great example of this look done right.
4. Over a Maxi Dress
For a one-and-done outfit, grab your favorite maxi dress and thigh high boots. I recommend opting for a-line, tiered, blouson, or wrap dresses in order to avoid any bunching that could occur if OTK boots are layers under body con and fitted dresses. From here, you can add any layers you need for extra warmth. I love wearing cropped outerwear with dresses, like a leather or moto jacket. A cropped, oversized sweater belted at the waist would also look chic and cozy.
5. With a Mini Dress
This is hands down my favorite way to wear knee high boots, especially for going out. I like to choose a mini with a flowy, feminine feel, long sleeves for warmth, and a fitted waist, like this one and this one. Fitted mini sweater dresses like this can also pair well.
6. In An All-Black Outfit
I love all black looks in the fall and winter, but sometimes it’s nice to add in texture or another neutral color to make sure the look is dimensional and interesting. Try a brown over the knee boots outfit with black skinny jeans, a black sweater, and a black coat.
How to Style OTK Boots
If you’re still struggling to feel great about your OTK boots outfits after experimenting with the ideas above, there are a few tips to keep in mind to make the outfit more seamless. I’ve also included notes on what to look for when shopping for OTK boots, as oftentimes a poorly designed boot can be the culprit in an outfit that just feels so-so.
- Pay attention to heel style when you’re shopping. When designed well, flat OTK boots are no less flattering and leg lengthening than heeled options. Wear heeled styles for an OTK boots fall outfit that’s chic and elegant, or grab flat suede thigh high boots for a comfortable-yet-stylish winter look you can wear walking around a city.
- Over-the-knee boots that have a drawstring at the top of the boot are a great option if you find that other styles tend to bunch around the knee area.
- Swap similar silhouettes in any of the OTK outfit ideas to expand your options. For example, the skinny jeans in outfit idea six can be exchanged for faux leather leggings or tights.
- Consider investing in a designer pair of OTK boots. Flattering ankle boots and chelsea boots are easier to find from budget-friendly brands, but the cut, height, and additional fabric of OTK boots makes them difficult to nail. At the very least, I recommend going into a store to try them on before purchasing. Pre-loved designer styles are usually available on Poshmark. Stuart Weitzman has been a favorite in the street style and blogger fashion community for years now—and for good reason. My absolute favorite pair of over the knee boots is by Stuart Weitzman. They nail the silhouette, are flattering on any body type, and they’re made to last. I also own and like my block heel Marc Fisher boots.