How to style a sleeveless dress Thatcorporatechic Sleeveless dresses still work in winter you just need the right layers. Five ways I'm wearing the same brown sweater dress in Northeast winter. Different moods, same base piece. Save Lets style a sleeveless dress for winter! Medium thickness dresses (not ultra summery fabrics) work bestturtleneck underneath, knit overtop and belted, add tights if its cold, boots, and a Sleeveless Dress in Winter