I see so many male characters being the popular school student and usually female lead is dowdy and poor. You might like the film Our Times, male lead is more of a thug but his reputation is well known. Female lead is not popular though, she's geeky and gets a makeover further in.
There is also historical school setting, SungKyunKwan Scandal which is awesome romcom. gender bender with female lead in disguise as a guy, she becomes slightly popular/well known while male lead is not very popular. There is also a forced living situation, and an almost love triangle.