How to Wear Dresses in the Winter Who What Wear RED Midi length dresses + high boots= yes you can. Normally I would pair this dress with pumps or a block heel but with winter here Im wearing taller boots to keep my legs warm throughout the day. Burgundy Velvet Dress With Long Sleeves: Christmas Gown, Winter Outfit, Plus Size Etsy Cute And Cozy Sweater Dresses For Winter 36 Cozy and Cute Snow Outfits That Make Leaving Your House Exciting