Sounds like you should take some soul searching time to consider these feelings. It's one thing to feel indignant of behalf of another and another to feel like you want to belong. That depends on how much you want to belong, to be fair. I know many cis guys who have wanted old fashioned (French pre-Napoleon) clothes to come back in style because guys could wear wigs, tights and frilly bows and still be considered hyper masculine and very male. XD It's a spectrum and as you mentioned, guys are held to a lot of standards, much like women. I personally would love to see a reversal of the songs being sung by specific genders... the girls oggling the guys going on about 'feeling pretty' but I'm just a fan of anarchy, LOL XDD And also, it's pretty attractive to me to see aggro ladies and cute, femme guys. By femme I mean dressing up, not feminine looking. Rambo in fishnets is just too awesome, sweaty hairy manliness and all :3
Also, I think you can be pretty if you want. Not sure if you think you are leaning any particular way, but I know all kinds of men who cross dress and they look very good, regardless of their body shape/size and diverse features! Confidence and being oneself can go a long way to being attractive in any sense, not just the attractiveness expected of stereotypes...