Maybe back in the 90's when that picture was taken...
That being said, he actually looks quite normal in that picture, especially when you take into account when it was taken. He still looks a little dorky, but still well within the norm for a teenager in the 90's.
I think the last time Chris looked normal (aside from the Carlos Chantor pics) would've been 2001 or so.
IIRC, he started to get really fat in 2002-2003 and his fashion sense became even more dated and glaringly out of style as the years went on.
A teenager wearing something like "The Classic" out in public back in 1998 would not be seen as fashionable or stylish by any mark. But it would still be understandable, especially if they were dorky like Chris. And while Chris wasn't exactly a poor kid in the 90's (unlike today), he definitely dressed like one (although part of that is probably due to Barb being a neglectful cunt and Bob being an out-of-touch Silent Generation geezer)
By 2002, that same person would be seen as a manchild freak or at the very least, an out-of-touch sped. Although, both of those are good descriptions of Chris in all honesty.