Winter Midi Dress Inspiration: Style Ideas Resortire 33 Midi Dresses To Pair With Your Favorite Boots This Winter How to Style Your Dresses with Boots in Fall and Winter 33 Midi Dresses To Pair With Your Favorite Boots This Winter Dress and Boot Outfit Combos to Totally Nail Late Summer Dressing 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.