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The prep school look was in contrast to the messy brightness so prevalent and its footwear was distinguished by penny loafers.
In the pilot episode, Rory is accepted to the prestigious prep school Chilton.
When Gilmore Girls began, 15 year old Rory received admission to the exclusive Chilton Prep School.
Perhaps they attend an exclusive prep school and are looking to make waves, or maybe they are searching for a method of rebellion against the cookie cutter prom queen persona.