my messenger almost always drapes on me, more so when it's less full, but even when i stuff it with everything possible it still drapes.
i love how unstructured, functional, and chic it is
the only thing that bothers me is the length of the strap. it's adjustable, but sometimes i wish i could adjust so i could wear it shoulder length, or across my upper back. it's too long for that. not a major concern i guess, since it IS a MESSENGER bag and was meant to be worn as so.