I personally cary bags because I always have crap to carry, and because I love them. I am pretty confident that I can pull of most of my bag collection. I used to be a little more insecure about things and would only do the messenger thing, but I have losened up and now have a lot of large shopper tote style bags. I think it is totally about what someone feels comfortable with. I don't expect a straight man to be walking down the street carrying a Balenciaga large moto, but it would obviously be more than fine. I tend to not use my more, let us say "feminine" bags (basicaly my Stellas, which I think I can only pull off at all because I am so thin and short that they look bulkier, otherwise more masculine on me than on most men) when I'm not in the city, some people can't handle it and it isnt worth the angst. I don't see why it is always such a big issue when men carry bags, are we not supposed to have a bunch of useless stuff to lug around everywhere we go? I do however love it when I do not need a bag, it is very freeing to be able to just throw your keys in your pocket and go.