Winter Style: Over-the-Knee Boots

I think we can all agree that winter is boot season, but while everyone is wearing knee high boots (including me) I want to take a minute to revisit the over-the-knee boot. I have owned two pairs of Stuart Weitzman over-the-knee wedge boots for many years and have styled them many times here on this blog starting back in 2016 in this post. A couple other favorite stylings of these boots are in this 2017 travel post in Japan and this 2020 fall outfit with a leopard coat. While boot trends can come and go, I honestly have continued to wear these year after year. Whether styling with dresses, jeans, leggings, or skirts, I have always found ways to style these boots to feel on trend. This season, I brought these over-the-knee boots back out of my closet to style with a wool military jacket (another piece that has been in my closet for many years), merino turtleneck, faux leather miniskirt (this one I wear on repeat in fall and winter), sheer tights, and this bucket bag that you first saw last winter in this post. This outfit is one that I have worn variations of many times, including during our Paris visit last winter, and all of these pieces are classic wardrobe heroes in my opinion. Please do continue scrolling to see more photos, links to similar pieces, and more of my picks for over-the-knee boots in a variety of colors, heel heights, and price points.

Wool Jacket: similar here or here
Sweater: similar here or here
Skirt: similar here
Tights: similar here
Boots: newer versions here or here
Bucket Bag c/o Sézane: exact here

There are so many gorgeous over the knee boot options this season, and it has brought back my love of my pairs that I have neglected for a few years for other styles. I collected a selection of my favorite over the knee boots for you to check out below. Be sure to scroll through to see all of my picks at a variety of price points:

What is your favorite way to style over the knee boots this season? Please don't hesitate to leave me a comment below to let me know. Thank you for visiting my blog today and I hope you have a fabulous week!