I bought the Small Classic Messenger a couple of weeks ago. I'm constantly told how "tiny" I am, standing at 5'3" on a tall day, and the small is huge on me. I thought about getting the medium initially, but it would have been entirely too large of a bag on its own. The bag is extremely well made and durable. The pictures make the bag out to be a lot darker than it is in person. The Empire Red/Graphite bag and its more of a burgundy and almost forest green/gray colored.

I was stuck in a downpour of rain and my umbrella didn't cover the bag, but by the time I got to school (after riding two buses and standing in the rain for ~20 minutes) everything in my bag was completely dry. I carry a 10" netbook and its super snug if I leave the sleeve on and put it in the laptop compartment. This bag will hold my netbook, its charger cords, my algebra textbook, my binder, my makeup bag and my wallet. I didn't like the velcro at first, and almost didn't buy it for that reason, but there are some days I just have too much crap in there to buckle it shut! The velcro comes in handy if you often find yourself carrying more stuff than you intended. I also use it to carry groceries home from the store.

The only reason I gave it 4 is because it has no grab strap. Some days I don't want to deal with slinging it over my shoulder, I'd just like to carry it like a briefcase. I wish there was one you could change into a backpack.