Maxi Dress in Winter Ideas Closetful of Clothes Can I wear black leggings with this dress or does it require pantyhose? I'm bad at dresses. : r lesbianfashionadvice 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 Hot or Not: Wearing tights in the winter Grand Central Magazine Your Campus. Your Story.