EMILY: [gives Rory a hat] Here you go. Now you look just like Tiger Woods.
RORY: Wow, that’s some hat.
Eldrick “Tiger” Woods (born 1975) is a professional American golfer and among the most successful of all time. He became the World #1 in 1997, less than a year after turning professional.
I can find no instances of Tiger Woods ever wearing a woolly hat such as the one Emily gives Rory, and clearly it’s going to take much more than a hat to make Rory look anything like Woods.
The Annotated Gilmore Girls 