Learning about lack of privilege

Recently John Scalzi made a post to explain how life is for those who aren't straight white males (SWM) to those same SWM people.  He talked about how it is like a video game and being a SWM is a lot like playing the game of life on the easiest difficulty setting - people give more weight to your opinion, you get more money for no reason, things tend to go your way.  He specifically wants to avoid the word privilege in his post and in the discussion that follows but obviously it is the core of the issue.  The best way gain an understanding of someone is to walk a mile in their shoes, of course, so how would a SWM like me gain such understanding?

There is an event where men walk in high heeled shoes to generate awareness about violence against women.  It gets attention of course because they look utterly ridiculous in high heeled shoes and it raises the question:  Why is such foolish, outrageous footwear expected of one gender and expected to be absent in the other?  In particular, why are the reactions to people stepping outside of stereotype so strong and negative?  I asked Wendy if I should do this sort of thing and she told me that I should not, but rather put on fake breasts, makeup and a dress and go out that way instead.  I don't know if she intended that I actually try to pass as a woman, as that would require considerably more doing, or simply look like a man in drag.

Clearly crossdressing isn't going to give me the perspective of someone who has lived an entire lifetime as a non SWM, particularly since it doesn't cause people to treat me as a woman, minority, or gay person.  I think it might give me some perspective on how people who refuse to conform to gender norms are treated though, and it certainly could get me some experience on doing things with considerably less privilege than normal.  I do all kinds of weird things that have people treat me strangely already like go barefoot everywhere but these things that I do now are all done because they are actually more comfortable or better in some way.  Putting on a dress isn't that - shorts and tshirts are eminently practical clothes and I have no interest in dresses outside this experiment.

I don't especially want to go to tremendous effort to disguise myself so I think if this is a project I wish to undertake I should probably not consider trying to pass as female.  Not least of course because I am one of those people for whom it would be exceedingly difficult.  I don't know that I could pass for a minority outside of a very professional makeup job (even then...) and I also have no clue what I could do to convince a random person I was gay without being ridiculous.  (Hey random person!  I'm gay! So, ummm, yeah, react naturally to that.)  Strangely the fact that this would be a big deal to many people is making me want to do it more.  People shouldn't care whether or not my clothes violate gender norms but they do care.  A voice inside my head tells me I am obligated to call them on their prejudices and make a scene.  That voice is the one that gets me in trouble.  

Of course, it is easy for me since I can go back to my normal mode any time I want.  This isn't about being allowed to live my life, just about learning a bit, which makes me appreciate how hard it must be for trans folks and others who violate these sorts of norms constantly.  I have the fallback of "I'm doing a social experiment, you have a problem with that?" and other people don't.