What Shoes to Wear with a Midi Dress Vessi Winter Midi Dress Inspiration: Style Ideas Resortire Dress and Boot Outfit Combos to Totally Nail Late Summer Dressing 33 Midi Dresses To Pair With Your Favorite Boots This Winter 4 chic ways to style a midi dress for different seasons Happily Ever Style 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.