I believe on of the reasons we feminize ourselves to the extent we do, one of the reasons we "need" to dress so badly is because we have repressed our natural feminine urge all our lives.
Many people here report being "caught" trying on feminine clothing when they were very young and getting scolded for it. Or forced to wear the objectionable clothing all day or all week long. In addition, as kids, any outward display of feminine behavior has been "corrected".
In other words, we have been molded by our culture from the beginning of our lives to be the stereo-typical "male".
Eastern philosophy says the goal is balance between the feminine and the masculine (yin and yang). However, in our Western culture, all of that repressed feminine behavior lies just beneath the surface most of our lives, pops up once in a while, but is never permitted to run free and integrate fully into our personality.
Sure, it pops up here and there, but for the most part, it is repressed.
At some point in our lives the pressure builds up to a point where it simply must burst through and manifest. At such times, we hit the stores and drawers and go into a "pink" frenzy to work the energy off.
I believe we learn from these pink episodes and perhaps work off some of the damage we have taken as a result of our forced repression. However, it's never really enough and the urge cycles back again and again.
So, I can't help wondering that if we lived in a perfect world where our feminine tending actions were never questioned or criticized, if perhaps we would not need to push ourselves to the extremes that we do in our attempts to feminize ourselves.
It's interesting to note that Western women have for the most part, achieved this perfect world. They freely swing from feminine to masculine in the space of a single day in both behavior and dress. However, and this is an important difference, you can always tell they are women. The incidence of females dressing and attempting to fully appear as men is very much lower than the incidence of men attempting to fully appear as women.
This can only be a "thought" experiment since this world does not exist -- for men.
Open your minds, use your imagination... What would you wear in the perfect world, how would you behave? Would anything be different? Would we be more balanced? Perhaps we would truly be more like women in such a world, able to swing back and forth between the poles as interest and necessity dictates. Would we look like men in soft, frilly clothing or would we still need to appear fully as women?