How to Style a Midi Shirtdress with Boots Poor Little It Girl 33 Midi Dresses To Pair With Your Favorite Boots This Winter What Shoes to Wear with a Midi Dress Vessi 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. 4 chic ways to style a midi dress for different seasons Happily Ever Style