Trip's wig
Oh my GOD, that was the worst wig ever. It didn't move or fall like real hair and I don't even remember cool guys having hair like that.
Not to mention, private/parochial schools of that time had (and still do, mostly) rules about how long boys' hair can be. It can't be long enough to touch the shirt collar. Trip's was way too long and he would have had to cut it to comply with dress code.