RORY: Do you want to wear docks or sneakers?
Dock shoes, also known as boat shoes. These canvas or leather slip-on shoes have rubber soles that can provide grip on a wet deck. They were invented in 1935 by Paul A. Sperry of New Haven, Connecticut, and designed to be used on boats. They became used as casual footwear in the 1970s, and have been fashionable since the 1980s.
The Annotated Gilmore Girls 
I always assumed Rory was saying “Docs” here – do the captions say “docks”? Boat shoes are sooo preppy. I feel like they’d be the exact kind of shoe Lorelai would mock rich kids for wearing – especially in the 70s/80s when they were trendy with her peers – whereas Doc Martens (often called Docs) are exactly her style and would’ve been especially so during the late 90s/early 00s. Plus Rory is wearing a pair a few episodes earlier in Rory’s Dance so we know they have them.
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I originally put Doc Martens, but then I changed it, because boat shoes are better for walking – more like an alternative to sneakers. They are also a very Connecticut form of footwear. The teletext says “docks”, I believe. But to be honest, I am not really sure either way.
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