How to Wear Over the Knee Boots

January 16, 2019

Over the knee boots have become a big part of my wardrobe. I wear them casually with jeans and leggings and more dressed up with skirts and dresses. Easily my most popular post to date has been how to wear ankle boots, so today I thought I would do a similar post on how to wear over the knee boots. I’m breaking down all the different ways to style them including easy dos and don’ts with each option. Ask me below in the comments if you have any questions.

How to Wear Over the Knee Boots – 4 Different Styling Options

First Things, First – What Pair of Over The Knee Boots to Buy?

When it comes to what pair/style of over the knee boots to buy, I recommend buying an affordable pair to try. This Goodnight Macaroon boot is a super popular blogger favorite. They come in black, tan, and grey. The heel is super comfortable and the slightly pointed toe is very flattering. I would recommend going up a half size. I also have the Stuart Weitzman pair. I have had mine for three going on four years now and still love and wear them just as much as when I bought them (on sale/with a credit I might add). They are a major splurge!!

If you are buying your first pair, I would start out with a flat or small block heel style simply because you will probably get the most wear out of them unless you are the style of person who wears heels all the time. My personal opinion is that a more fitted pair like one of the pairs I am linking is a better, more flattering option than some of the more looser fitting styles available. They give a slimmer leg line.

How to Wear Over the Knee Boots with Jeans – 5 Examples Below

Pairing over the knee boots with jeans is the most casual option and probably my most worn styling option. The top pairings are endless. You can select a blouse, sweater, or really anything.

DO pick very skinny jeans to go under your boots. Do consider highlighting your waist by tucking/front tucking your shirt or wearing a peplum top (more on how to tuck your shirt here). The other good silhouette is an oversized sweater/tunic top as you have a slim legline with the boot. An example of this is my green sweater in the third outfit example below.
DO NOT pick straight leg jeans, only very skinny pairs work. Do not let your jeans to bunch underneath creating unflattering leg lines.

How to Wear Over the Knee Boots with a Skirt – 2 Examples Below

I love pairing an over the knee boot with a skirt, especially in the winter as it keeps you warmer! As a taller girl, I also love how these boots add some coverage.

DO let your skirt hem hit above your boots. You can add tights as well if you like. Some visual difference between your hem and the boot creates a more flattering line.
DO NOT wear a full style mini skirt. Either wear an a-line style or a fit and flare. Though I don’t have a photo of it, I also love a midi skirt styled with a sleek over the knee boot underneath.

How to Wear Over the Knee Boots with Leggings – 3 Examples Below

Leggings are a natural choice to wear with over the knee boots since they so easily fit underneath.

DO wear a longer sweater, top, or cardigan over your leggings. In the first two examples below, I have on a long sweater. In the third (sorry, throwback pregnancy pic), I am wearing a tunic length top with a cardigan over it.
DO NOT wear a short top. The combination of a short top that doesn’t cover your bum with over the knee boots and leggings would have you looking a little less than classy.

How to Wear Over the Knee Boots with a Dress – 3 Examples Below

Similar to why I love over the knee boots with skirts, pairing a boot like this with a dress is a fun and sassy way to style a shorter dress for winter. As opposed to wearing tights and heels, this gives more coverage and warmth.

DO let your hem hit above your boots. You can add tights as well if you like. Some visual difference between your hem and the boot creates a more flattering line. You can also style a midi dress with over the knee boots in which case you wouldn’t worry about the hem. You just want one or the other – boots above the hem or totally covering the top.