^^^exact same issue with my black bag, which pissed me off for all of five minutes until I realized I could tuck it somewhere else and it didn't matter. What's a real messenger? Someone like Squid, or someone who's a grizzled old man who's a messenger because he can't do anything else? Anyway:
http://www.pacdesigns.com/firsts.htm are no joke and will last you forever. I have a seagull black bag, which I like a good deal and carries everything from groceries to frames. I also have a crumpler, which isn't really that good. It's not a bad bag, but I wouldn't recommend 'em. Chrome has a stigma attached to it, but on a whole are not bad. I don't know much about baileyworks first hand but they seem wholly inoffensive and perfectly capable. ReLoad bags are nice, if you're willing to spend the money. Don't bother with incase. Don't bother with timbuk2. Don't bother with manhattan portage. Freitag bags are pretty fucking cool and pretty niche; by all accounts they work well, but they've got a pretty hefty premium attached to them. Are you a hypebeast? Pick up a Sag bag, vertical or otherwise. As far as I know, they're the only bag company that does Sag x whatever. Check this out for some others that I might not have mentioned:
http://www.messengers.org/resources/bags.html