In terms of "frat prep" I think you're going off a slightly idealized view. SEC is not that nice. It depends more on the house itself and where the majority of brothers are from. (and to some extent, money) I think it comes to valuing brands as well, I haven't bought a Ralph Lauren blue label polo in ages because the quality is actually a joke. But to most people, blue label is considered sacred and the best money can buy. I think preppy is best done when the logos are only visible when the clothes are not tucked (shirt tails etc) or not visible at all. Running around in matching polo cap, shirt, shorts and sperrys just looks funny. When I wore a much nicer boat shoe than Sperrys people called my shoes "knock offs" and said Sperrys are 10x better. That's the kind of prep that pisses me off. And also boat shoes are NOT business casual or formal shoes, it's embarrassing to see people wearing them to formal chapter.