Wearing a Sleeveless Dress in Winter 9 super easy ways to wear dresses in the winter and not freeze Dress Winter Sleeveless TikTok 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 dresses still work in winter you just need the right layers. Five ways Im wearing the same brown sweater dress in Northeast winter. Different moods, same base piece., Save this if you Summer Style tips: What to wear over a sleeveless dress