Struggling to know what to wear ankle boots with? Or not sure how to wear ankle boots with your fall casual outfits? This ultimate guide to wearing ankle boots will help you wear your ankle booties with your casual winter outfits. It shows you exactly how to wear ankle boots with jeans (mom jeans, straight leg jeans, skinny jeans) how to wear ankle boots with a dress, how to wear ankle boots with skirts, and all the do’s and don'ts of wearing ankle boots.