RORY: Too cool for school, huh?
A phrase that seems to have arisen in 1950s hipster culture, to mean that someone has submerged themselves in the counterculture to the point that they no longer fit in with conformist society. Once used as praise, today it’s usually used sarcastically, as Rory does, to mean the person is too pretentious or above themselves to lower themselves to normal standards of behaviour.
The Annotated Gilmore Girls 