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. Dress and Boot Outfit Combos to Totally Nail Late Summer Dressing What Shoes to Wear with a Midi Dress Vessi How to Style Your Dresses with Boots in Fall and Winter Midi dress & over the knee boots 33 Midi Dresses To Pair With Your Favorite Boots This Winter