I agree with the guy above who siad that it comes down to preference. If you are looking at moving to a messenger bag, I'd recommend borrowing one from a friend & taking it for a few rides to see if you like it. I bought one & never could get used to it. I felt it was significnalty less comfortable than a backpack. Lots of people agree wtih me. Lots of other people love them, so to some degree it comes down to preference. If you borrow one from a friend & like it, then there are a lot of good options listed above.