LORELAI: Hi. Things bad out there, huh?
RORY: It’s crazy. There’s snow coming down everywhere, and let me just tell you, saddle shoes are not the best all-weather footwear.
Saddle shoes are casual two-toned Oxford shoes that have a distinctive “saddle” shaped decorative panel over the middle; they were popular footwear in the 1950s. They are often worn as part of a school uniform. You can see Rory’s black and white saddle shoes throughout her years at Chilton.
The Annotated Gilmore Girls 