Seriously, Chaz*, please explain yourself.
Apparently Chaz here heard about Foxfield's preppy prerequisite and showed up last year with four shirts to achieve serious collar poppage. But he was hot--and I don't mean sexy. This year, he wanted to up his game AND be cool, so he did a little research. What we see here is Chaz sporting two shirts, and seven dickies.
Next year, you may ask? Chaz is plotting out all the little figurines he'd like to embroider on his seersucker, patchwork shorts. Keep an eye out for 'that guy'...!
*Chaz is a conveniently preppy nickname designed to prevent Carlton's students from knowing it was really him.