There has been a lot of criticism
You can trace his evolution a little more carefully. I believe this conversation was about a time Chris was tricked into releasing a picture of him wearing his mother's underwear. Which he was upset about and didn't think meant anything. Fair point to him I think.
Then there was the muscle bra incident. He had some moobs which apparently were causing him problems, and decided to buy some sports bras. I suppose that is fine. But his reactions to wearing it was so over the top.
"OMG, WOW! This material feel so, so, so good on my skin. It's like a
Guitly Pleasure or something."
That quote is quite telling to me. That is a ridiculous amount of satisfaction. Maybe other guys with pronounced breasts find them nice to wear when exercising. But a 3 for $10 bra feeling so so good on his skin? I don't really buy it. And the phrase guilty pleasure is pretty telling.
I think that is one of the first signs of his transvestism. It really sounds like he had a bit of an epiphany when he put the bra on. I think that this is decent evidence that there is more to his transvestism than just an attempt to get attention or china. There is something fundamental about dressing as a woman that appeals to him.
I respect Chris' commitment to wearing women's clothes. Sure it looks bad, but he puts up with a lot of shit from his mother, and others I am sure, to do it. It doesn't really give him any tangible benefit, and it isn't a product of laziness. He is actually standing up and very publicly representing a fundamental aspect of his identity. For a man who isn't known for bravery or strength, this is a fairly brave and strong thing.
As an aside: I have always been intrigued with trensvestite's motivations. I wear "male" clothes because I am male, and that is what males do. I don't feel that wearing pants rather than a skirt means anything fundamental to me. If I home alone and not going to see anyone, I wouldn't care at all about what I was wearing. So I don't have a great understanding of the the idea of someone "being more comfortable" in the clothes of the opposite gender. I don't dispute that it is very real, it just represents a much more fundamental attachment to clothes than I have ever felt. But Chris has always felt that clothes are fairly fundamental. He took the classic shirt very seriously, took Liquid Chris' brown shirt very seriously, took the ring and medallion very seriously. Even in the clown shirt era, the way he talked about his clothes being a part of his identity was somewhat reminiscent of the way transvestites think about it. I don't know if that means anything.