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What the hell are you talking about? You must live in buttfucking egypt if you a messenger bag is gay.
:werd: messenger bags have been a basic for like 6 years. They're OK. I like these slingpacks, I used to have one as a purse. And I don't think they look remotely stupid on guys. I wouldn't even consider them trendy. If its for comfort, then its not trendy for men. Thats your rule.
I always found them incredibly uncomfortable. For years I used a messenger bag, now I've switched to tote bags (which is definitely gay for men, but us girls can do it just fine)