As others have already said, I also don't believe wearing clothes designed for another gender truly qualifies as cross-dressing. Plenty of us, girls love to wear men's shirts and tees with NO intention whatsoever to appear masculine. I actually think it's one of the most feminine things one can do
I also don't believe it was Michael intention to do any real gender bending with his choices of clothes either. Thank goodness he stuck to the clothes only, can you imagine what it would have been like if he had actually pretended to be a woman? lol
The pictures posted demonstrate his more or less sudden interest in female fashion back in 2008/09, but during the same period I've noticed a truly disturbing (let us call it) trend in which he would wear skulls and stuff. As far back as Halloween 2008 if I'm not mistaken up till that ugly, white t-shirt in early June 2009. They kind of have a strange and prophetic feel about them in the context of what took place on June 25th.
On a lighter note now - I actually have somewhere on my computer a funny picture which could fit rather well in the context of this whole convo about genders wearing all kinds of items, but I'm afraid it is a bit to spicy for now. I guess I'll have to dig it up at some later point in time........