Autumn in New York (2000)

The film itself may not have been awards worthy, but the fashion in which it portrays fall captured hearts. In Autumn in New York, Richard Gere plays a 50-something New York playboy who happens to fall (no pun intended) for Winona Ryder's character, an ailing woman half his age. It's a sorrowful story, but the radiant colors of New York's leaves are enough to entice any viewer.