I think the main problem with Chris's sense of fashion is as you said he thinks X (
pulled from 90's TV sitcom) means he will have result Y (
China or Fame an Fortune) if you do or look like X so once you add the derailing factor of his autism we get result Z.
But I also think there is other factors in play one of the big ones is his access to fund's and how he choses to spend what he has available, and he has never done anything other than use them to plug a hole in his want list not his need list (not even long term stuff like a house or a car, but short term need stuff like clothing) and he hasn't got much of a body image either, the saying "
The cloths make the man" is kinda fitting in a perverse way in this case. Back in the Rugby shirt era, Chris did look how TV portrays special needs people look (
chubby, poor taste in clothing dictated by his Mother, the child molester glasses), and in the current Tom Girl saga he looks exactly how we kinda picture half arsed fetishist transvestites look (
Cheep, Trashy and quite amazingly ugly). At the moment he is still just plugging the hole in his "I want this" list, his clothing is cheep as he does not see the point in looking some what normal as to his autism filtered eye's what he wants is normal as it is him wanting it and using the path of least resistance to get it.
While I am not going to stretch this into him getting a better personal image (
or his own identity outside of Barb as we are seeing this unfold now with all the horrific details therein) would turn him into the worlds best dressed Man, Woman or Man-Child as that's never going to happen but it might help him at least look
normal in passing at least but the longer the Tom Girl thing drags on and with the developments in the last few day's that caused me to register on the forums I can see that some what remote possibility drifting further and further away.