In S1E4, Lorelai is arguing with Headmaster Charleston about his refusal to let Rory take a test. Lorelai says, “I thought this place was gonna be so great, and now I guess this goes on the ‘Boy was I Wrong’ list, right above gauchos but just below the ‘Flashdance’ phase.”
The “gauchos” that Lorelai is referring to are a style of pant, usually cropped at mid calf, with legs that flare out very wide. Gauchos were popular in the 1970’s and actually made a comeback in the 2000’s, just a few years after Lorelai first said this line.
“Flashdance” was a 1983 film in which an exotic dancer works to get into a dance conservatory. The movie currently has 33% on Rotten Tomatoes.