Every Fall, over-the-knee boots emerge on the runway looking impossibly chic and wearable. Retail stores line their shelves with options of all sorts, from suede to leather, black to navy, and lace up to stretch. But if you are anything approaching average height, it’s impossible to put on a pair of thigh high boots without feeling like an extra in Pretty Woman.
In real life, over-the-knee boots seem too dramatic and overwhelming. They tend to make most women look shortened and even a bit clumsy.
I have good news for you though, it’s entirely possible to pull off the thigh high boot. You just have to think about fabric and proportion.
Take Olivia Palermo for example. She’s wearing her boots in a muted way that yields a strong effect overall. She chose to keep her clothes and shoes in all black, creating a clean, uniform look. She used leggings to continue the line created by her boots, and then balanced that shape with a cape to add a touch of femininity. The large bag in black and white builds drama without taking away from her overall silhouette. This isn’t an everyday look for most of us, but it’s absolutely wearable for brunch with friends, or a shopping trip with the girls.

A simpler way to do it is to pair your boots with a turtleneck sweater dress like the photo above. This creates a feminine and comfortable look, with the added sexiness of showing a touch of skin at the thigh. It’s easiest to stick with one color for this, and makes a really strong statement in black.

If you want a more modern approach, try pairing over-the-knee boots with a topper coat. The extra length of the coat has the same ease as the sweaterdress, but with a more structured feel. For coats, try an A line shape in wool.