How to Style a Midi Shirtdress with Boots Poor Little It Girl 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. HOW TO STYLE MIDI DRESSES FOR WINTER JustineCelina Flattering Knit A Line Midi Dress for Winter Styling Midi dress & over the knee boots Winter Outfit with Midi Skirt, Shearling Jacket and Leather Boots