What to Wear with Sleeveless Dresses: Helpful Ideas & Concept 11 Ways to Wear Dresses in Winter and Still Stay Warm Style Tip: What To Wear Over Sleeveless Dresses Cyndi Spivey Wearing Sleeveless Layers in Cooler Months Numi 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 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