How to Wear Dresses in Winter Layering Under Dresses Warm, comfortable, and polished., A black dress with tights and boots is one of my go to winter combinations., If you ever feel stuck getting dressed in cold weather, start with a neutral base and The Oversized Leopard Print Sweater I'm Wearing on Repeat This Winter Sarah In Style Someone asked me "how do you wear your cotton dresses in winter?". I layer them polo neck underneath, leggings and knee height boots. I need to invest on fleece lined tights though, I've seen SNOW LEOPARD HOUSE of HARPER HOUSE of HARPER