I’m a self diagnosed ankle boot addict. I have an absurd amount of them; ranging from several versions of the chelsea ankle boots to moto ankle boots. When I first started wearing them I had no idea how to make them look good and how to not look insanely short in them. For most ankle boots when you wear them with pants you should cuff them, there’s tons of tutorials out there explain the do’s and don’ts of ankle boots. However, slouchy ankle boots seem to make the exception.