The 12 Best Dresses to Wear With Boots | 2023 Guide

With brisk, cold temperatures on the forecast for the foreseeable future, I’ve been trying to think of more cozy outfit combinations that don’t only involve comfy jeans, chunky sweaters, or the same winter coat that I’ve basically been living in for the past four months (the cold weather fashion fatigue is starting to get very real, folks!). While layers might be the name of the game this season, that doesn’t necessarily mean you have to sacrifice your own personal style to embrace them — or set aside your favorite dresses, for that matter. Transitioning all of your go-to summer and fall dresses into chic winter styles can be as simple as matching them with a great pair of boots and some tights — turning even the flimsiest dress into a darling winter look that packs ample warmth and style.

My guiding style principle when it comes to wearing dresses with boots is to mind the proportions. Ideally, any combination of the two would elongate, support, or enhance your figure, rather than appear forced or constricted. To help you nail the dress-and-boot combo this winter, I went ahead and shopped out a handful of frocks that you can easily throw on over your favorite boots. Whether you’re opting to wear a long dress with ankle boots, a short dress with knee-high boots, or even a midi dress with Chelsea boots, the styling opportunities are truly endless. Scroll on to shop our picks for the best dresses to wear with boots this season!

— Additional reporting by Shelcy Joseph