How to Style Dresses and Knee High Boots for Winter 2025 Who What Wear 12 Ways to Wear Boots with a Dress This Winter Busbee Style 5 Editor Approved Looks to Wear to Your Next Holiday Party Who What Wear How to Wear Dresses with Boots (a simple style guide) 15 Ways to Wear Dresses With Boots This Fall 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.