I used a messenger bag for a long time before a snow boarding incident made it uncomfortable. Now I use a backpack. I've long since healed and I'd be probably be fine to go back to a messenger bag now, I just haven't

Anyway, the big advantage of a messenger bag over a backpack is that you have easier access to your stuff. You don't need to take a messenger bag off to get something out of it. Since it is wider than it is deep where backpacks tend to be the opposite, everything is more accessible.

So why am I using a backpack instead? Because my old messenger bag is showing its age and not as waterproof as it once was. I'm not happy with the way the buckle is set up on it anyway. So I if went back to a messenger bag I'd want to invest in a good one and I have a slight fear that the pain in my shoulder might come back and that I would have made that investment for nothing.

In other words, the backpack I have is comfortable and I've learned to live without the extra convenience a messenger bag provides. Personally I don't remember a messenger bag being any cooler but it has been awhile. I guess it doesn't make much sense to me that it would be.