Some of the college fashion stuff is very interesting to me. Well, one of the specific pieces--the Cub Scout bandana--is interesting. While the rest of his ensemble is clearly inappropriate outside of a too-long-postponed laundry day, the bandana wouldn't have seemed totally out of place to me at that time.
I must acknowledge that the bandana was clearly out of place at ASU in the late 90s. We have both visual evidence from the other students' yearbook photos and testimony from a poster who was there at that time. However, in a larger cultural sense, in 1997-98, among college-aged people, there was still a good bit of hangover from the burst of retro/futurist/weird-positive energy in the mid-90s, which itself had been influenced heavily by the slacker culture of the early 90s. Basically, think of how the people in Richard Linklater's Slacker dressed: that was subaltern hipster gear in 1991, and by the mid-90s elements of that style had become...not mainstream, but also not exactly strange. It would be an odd or try-hard look for an engineering, business, or education student, but it was a valid option for English or philosophy students.
Wasn't he wearing the bandana with an Army surplus jacket? I'm too lazy to go look right now. If he was, that's exactly the sort of combo that would have seemed appropriate at that time (but not, apparently, in that place). With an Army jacket you'd be going for a sort of ironic/detached look; you could also wear a Webelos bandana with, say, a t-shirt with a cartoon cereal mascot for a more whimsical look.
The problem is, even if he got two pieces that would go together within the parameters of a particular faddish style, he clearly missed the attitude that the style represents. Sweet is all about sincerity--brash, obnoxious sincerity that attempts but fails to use verbal irony, but still ultimately sincere instead of the bemused ironic detachment that the look requires. And then, of course, he ruins it all anyway with purple fucking pants and a grandpa-worthy novelty cap. (Although the cap itself could have been a failed attempt at capturing the ironic-or-playful appropriation of advertising ephemera into personal style.)
What I'm saying is, I think the bandana might have been an attempt to mimic the style of some people he considered cool in magazines and other media of the time. It was not a locally acceptable style, though, and he failed to realize that you can't successfully take just a piece without adopting an entire look unless you're both hot and charismatic, but the biggest problem is that he failed to understand what made the style work for some people and why it wouldn't work for himself. Which, really, is no surprise at all. Clothing is a form of language, and we have ample evidence that using language effectively and well is not his strong suit. (If pressed, I'd guess his strong suit is "picking up cans by the side of the road." He's probably not especially awful at that.)
(I...I think I've just revealed how I dressed in the late 90s. I swear, though, at least a quarter of my local peers dressed the same way!)
