I was late to the Over the Knee Boot trend having bought my first pair last year (see this post) but they soon became my favorite purchase. I wasn't sure how practical they would be or how often I'd wear them. But I've actually wore them 7 times in a year! How do I know that you ask? lol I use the Stylebook app to organize my closet. I love how OTK boots seem to make an outfit feel luxe and they are perfect for fall and winter seasons. The boots I got are flat so they are very comfortable to wear but still feel dressy. You can wear them with a sweater dress, a skirt, over skinny jeans or here I paired it with a fit and flare dress. These have definitely become one of my favorite purchases as they are keep you warm and are great for when you don't want to wear tights with your dresses.
I challenge you to try one of the hottest trends of the season, even if you are skeptical if you can pull them off. They elevate any outfit they are paired with! Below you have so many choices to choose from in many colors, I think you will be pleasantly surprised how well they will work for you. If you have wide calves, some of the linked shoes have elastic at the top so you can move with ease. Some of the boots have side zippers to make it easier to put on. The super tall ones are reminiscent of the boots Julia Roberts wore in Pretty Woman. I hope you find the perfect pair!