In S1E1, Lorelai meets Rory in the kitchen of the Independence Inn and hands her a bag with a plaid school uniform skirt in it. When Rory sees the skirt, she guesses, “I’m going to be in a Britney Spears video?”
Britney Spears is a pop singer and childhood actress. Her first album, “…Baby One More Time,” debuted in 1999 and is one of the best selling albums of all time. The wildly popular music video for the record’s title track features Britney as a Catholic schoolgirl, which is why Rory referenced the video when she saw her school uniform.