I'm only 5'2! I thought I'd like the small too until I went into a store and tried on both in the shiny calfskin. The longer drop of the small gives it a different look and I personally prefer the shorter drop, which I feel goes better with the slouchy hobo style.This bag is stunning! Can I ask how tall you are? I think I want the medium as well however I’m tempted by the small as I like the longer drop since I’m 5’8”.