I believe your theory is sound Paige, mostly because I know that as human beings, we are all a mixture of both male and female and we all have the capability of the full spectrum range of feelings as a genetic heritage regardless of what our physical sex is. The willingness to embrace those feelings is what remains in question though, especially in view of (sometimes harsh) societal programming. Because of that most men tend to suppress these feelings and urges which quite honestly are completely natural and dressing is an outward demonstration of that.
How many little boys have tried on Mommy's lipstick because they wanted to be like Mom only to be threatened with ostrasization? How many boys enjoyed playing with the girls but would never admit it for the same reason? As a society we tend to shoot ourselves in the foot with this stuff because what we may consider "right and proper" may not be necessarily so as far as people are concerned. I know one guy who was so afraid of being accused of being feminine, he would not even touch his wife's purse which is totally absurd.
It's all part of exploring really, especially exploring one's self and contrary to popular opinion, that does not end once we "grow up".If we are denied exploring who we are and why we do things, especially by ourselves we are doing ourselves a disservice and quite honestly our full potential as a person is never realized, no matter how "successful" we may seem to be.
In any case, most men don't have the gumption to do this on their own and need an excuse, usually Halloween or whatever to justify their behavior. While sometimes TG folks may take advantage of the same opportunity, their intent is really to get in touch with themselves and their feelings. To me it takes a real man to admit his feelings regardless of what he looks like.