I really like this bag. I am a sucker for messenger bags (I own far more than I'll ever use) but this one might be one of my favorites. Water resistant, holds all sorts of useful and necessary stuff and looks good, too. I bought the small. Honestly, I think the small is plenty for most people. The medium is huge and might be heavy to carry if you packed full of as much as it could carry. I got mine in Grey/Cold Blue/Tusk Grey and it looks sporty and handsome. Go ahead and get a TimBuk2, I think you'll enjoy having one.