LORELAI: Ooh Dad, see if you can find a pair of the new Chanel patent leather pirate boots stuffed back behind your Churchills.
Chanel, fashion brand, previously mentioned.
Patent leather is that shiny, almost plastic-looking, leather, and pirate boots, more correctly cavalier boots, are knee-high boots with a cuff around the top. A pair of Chanel boots of this type could cost around $1000 today. The boots sound suspiciously like something Amy Sherman-Palladino would wear.
The Annotated Gilmore Girls 