RORY: How did [Tristan] fall in with those guys [Duncan and Bowman]?
MADELINE: The new year started and there they were, all three of them, side by side.
LOUISE: And practically dressing the same.
MADELINE: It’s very On the Town.
On the Town, a 1949 musical film directed by Gene Kelly and Stanley Donen, based on the 1944 Broadway musical with music by Leonard Bernstein and Roger Eden. It stars Gene Kelly, Frank Sinatra and Jules Munshin as three sailors with a day’s leave in New York City, and their romantic escapades. An immediate succeess, it won the Oscar for Best Music and is regarded as one of the greatest musicals.
Like the three sailors, Tristan and his new pals all dress the same – although as there’s a school uniform, doesn’t everyone dress the same anyway?
The Annotated Gilmore Girls 