Each Gilmore Girl has her own specific style. This is even true of the grandmother Emily. We also see a lot of the characters throughout the show who really develop their own personal style. This is even true of Rory’s best friend Lane.
She always seems to have a punk rock look kind of going on. At one point she really even tries to dye her hair purple, but although she really loves how the look she just doesn’t want her mother to disapprove. So she dyes it back to black before anyone else finds out. She wears thick glasses and when she tries to get rid of them and go for contacts she finds that everyone really protests. They love this adorable girl next-door or smart girl kind of persona that she had made for herself and they really don’t want her to change that. She’s constantly worried about what she will look like on an album cover if she finally does get her big break musically.