LUKE: I was crazy, and now after all that has happened, after all the chaos and havoc that you have wreaked, you’re seriously standing there wearing a T-shirt with a picture of a butt with hands that are flipping me off, telling me you wanna come back?
Although Luke says that Jess is wearing a tee-shirt depicting a butt with hands giving people the bird, this is not visible in the scene. It looks as if Jess is actually wearing two tee shirts, a grey one over a black one, topped with a dark windbreaker jacket.
The Annotated Gilmore Girls 