Well, I've been carrying a Tumi-like bag for ages (replaced 3-4 of them during the last 9 years as I really hate stuff in my pockets). All of them were intended for carrying still/video cameras or gadgets. When I started carrying one nobody here (Israel) carried one of these (Waist pouches were popular and I really-really hated that look). Today side bags are very common and people even carry their 9mm handguns in it (I'm not joking!). It's usually this look: View 1:
Nobody here thinks you're a sissy for carrying one (bag not gun). Anyway the Freitags are carried accross the shoulder like a small messenger bag:
See photo 2nd from the right (Ingnore yellow collor). I agree that carrying it by hand (2nd from left) doesn't look very masculine. As for the cinch alternative suggested by Smooth Genes - these were popular among kids here 25 years ago and you can't see them around today anywhere - Fashion is very location-related you know. Also as you become older (I'm 36) you develop your own style and don't really care about what others say (That's very teenage like). I'll take your advice though and won't carry my bag around when I'm in the States and avoid those cinch-bag-carrying-goons you were referring to (If they do mock me I'll hit'em on the head with my purse, er side-bag.) P.S.
Unless you are a flaming homosexual i highly suggest you do what the rest of us men do, stuff your pockets full of all your shit and live with it.
I'm not a "flaming Homo" (Not that there's anything wrong with it!) or whatever that means, I just hate it when my pockets are full and I do have to carry stuff around. Cheers, Chipopo