Debbie Styles Life as Debbie This and That: How To Wear A Summer Dress In Winter and A New Year's Video Style Guide: How To Style Dresses in Winter 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 This styling trick turns (almost) every summer dress into a cosy winter look WhatWonderWomenWear 6+ Options of How to Wear Summer Dresses in Winter 10 Smart Ways to Shift Your Summer Wardrobe into Winter Without Breaking the Bank