Style Guide: How To Style Dresses in Winter How to transition your summer dress into fall TallFashionBlog My favorite way to winterize a summer dress is to throw on a wool sweater, some tights (this pair is from @snagtights, theyre the best), and a comfortable pair of boots. I sewed an elastic loop and Styling a Summer Dress for Fall and Winter High Latitude Style 10 Smart Ways to Shift Your Summer Wardrobe into Winter Without Breaking the Bank Debbie Styles Life as Debbie This and That: How To Wear A Summer Dress In Winter and A New Year's Video