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on one hand, i do see what you're saying about the shirts and how promoting the idea of what "real men" do and don't do is a bad thing.
on the other hand, i had a (guy) friend in high school who had a hot pink shirt that said "real men wear pink," and i think it took a lot of courage to wear it. he went to an all-boys school. this particular school was...really, really big on being hyper-masculine, perhaps because it was a conservative, catholic, military academy. showing the least bit of anything that wasn't uber masculine was not very well accepted.
i think that....sometimes the "real men wear pink" shirts are just trying to show that people who are truly secure and confident in their masculinity can do want they want, without regard to what everyone says a man must do. i'm not saying that i think a person can't be a real man without wearing pink, just that i think if you're really secure in your masculinity, you can just let it be and not be so caught up in always always always flaunting your masculiniity and making sure that everything you do always conforms to society's masculine ideal. also, i'd like to say that, although i recognize i'm using both words, i'm wary of saying things about what makes something/someone a "real" something or "really" something; so, please, take what i'm saying with a grain of salt.
maybe the pink shirts are showing insecurity by saying that other men (who aren't wearing the shirts) aren't "real men." maybe the pink shirts are saying that the men wearing the shirts are comfortable with who they are, regardless what they're wearing. i don't know.