“We all get dressed for Bill,” says Vogue Editor Anna Wintour about Bill Cunningham, the legendary yet enigmatic New York Times photographer. This intimate film captures the spirit of the intensely private 80-year-old and unlikely man-about-town. He has been riding around New York City on his bicycle for the last forty years, documenting fashion for his weekly column “On the Street,” in which he identifies trends as he spots them emerging on the street. The result is far from simple picture-taking—it is cultural anthropology. This deeply personal film is not only a portrait of this elusive fashion icon, but also a portrait of New York City itself.