Layering Tips: Best Toppers to Wear Over Dresses How to Wear Dresses in the Winter Who What Wear You can wear your summer dresses in the winter. Im wearing a black spaghetti strap dress and threw this sweater over it, tucking it into a black headband around my waist., #outfitinspo I have a dress like this(without the ruching) very tight. It has spaghetti straps and an open back. Can someone help me dress it up for winter? I have stockings. Thanks!