That was a style then. It may not be your thing or mine, but it's not puzzling that someone was caught up in a fashion style of the times.
replyIt was a thing for a while in the early 2000s, mostly as a preppy status symbol. It was pretty much iconic SV founder uniform for a short time.
replyIt was a preppy frat bro look of the mid-aughts.
replyIt got pretty ridiculous. I had a few people in my classes that would do 4+ layers and show up looking like an artichoke.