How to Wear It: Over-the-Knee Boots

I’ll be the first to admit the styling over-the-knee boots can be tricky. We’ve seen leggy celebs gracefully wear over-the-knee boots and make them look effortless and chic over the past year, but celebs do that with pretty much everything. After test-driving a pair of Stuart Weitzman’s iconic 5050 Boots and finally getting my feet into a pair of my very own Christian Louboutin’s Armurabotta Over-the-Knee Boots, I’ve had my fair share of practice styling what can be a very bold look. While my Louboutins are easily one of my favorite pairs of shoes, it took some practice to learn how to style them because of my short stature. I’m slightly under five feet (but if anyone asks, I’m 5’2″ due to my hair), and I’m here to share what I’ve learned.

When styling OTK boots, the most important things to think about are proportion and contrast. For example, to avoid looking too risqué for the office, I like to wear mine with jeans, as opposed to a pair of form-fitting leggings. For maximum boot exposure, I also like to contrast dark OTK boots with a lighter pant. Pairing OTKs with flowing textures and feminine prints is also a great way to wear your boots in an appropriately casual way.

Another thing to keep in mind when buying a pair of OTK boots is where they fall on your leg, and for me, this was the biggest key. Any boot that comes just ever-so-slightly above the knee doesn’t work for me because it digs into my thigh and makes my legs look like they are protruding over the boot. (Trust me, not flattering!) OTK boots that come to my mid-thigh work best for comfort and for my body. Finding the perfect fit can be tricky, but once you master the art of the OTK boot, they may quickly becoming your favorite pair of shoes.

Below, check out our styling suggestions for the super-popular (and celeb favorite) Stuart Weitzman Highland Boots.