What To Wear Over A Dress In Winter To Beat The Chill How To Wear: Sleeveless Dresses in the Winter! Layer Under, Layer Over! Add a little scarf and add a hat too if you're extra chilly! Take this look and add some tights How to Style a Sleeveless Bodycon Dress for Cold Weather Look, Ma, No Sleeves! How to Wear a Long Sleeveless Vest with Style Wearing a Sleeveless Dress in Winter