My initial thinking is that he probably won't ever completely grow out of it, based on my own experience--but then to me, at that age dresses and panties were forbidden fruit (as I lived in a house with no sisters) which increased my fascination with them. Even the few chances I had to be dressed up as a girl by my female playmates, I didn't take, as that "boys don't do that" voice in the back of my head made me hesitate (my advice to youngsters in that situation would be, don't hesitate, let her do it! :P ). So, perhaps being allowed to wear a dress and even have a dress of his own will lead him to get past this "phase" and go on to something else. Or, it could just let him develop his future CD fashion sense...hard to really know.
