By the time this famous exchange takes place between Woody Allen and Diane Keaton in Annie Hall, the Oscar-winning film released on this day in 1977, the actress had already made an indelible sartorial impression in at least half a dozen scenes. From chasing lobsters to seeing movies to playing tennis, Annie consistently puts forth a one-of-a-kind style that combines a curious mix of dichotomies: masculine and neurotic, frumpy and tailored, haphazard and thoughtful. But the outfit that inspired the “Annie Hall Look”—men’s khakis, white cotton dress shirt, fedora, vest and Grammy Hall’s tie—not only created a catchall phrase that would forever-after define any woman’s outfit that incorporates a man’s vest or tie, but created a style icon out of Keaton and an entire genre of dressing for women. How much time will pass before any other woman but Keaton could wear the same combination of clothing and not be likened to the actress’s most famous role?
For her part, Keaton required no stylist for the film; the Annie Hall look is Keaton’s own weird look. It’s a style defined by modesty—or a literal personification of Keaton’s own neuroses—that appears to be driven by the goal of hiding as much skin from the chin down as possible. Allen supposedly loved Keaton’s real-life look and refused, against the producer’s wishes, to have her professionally dressed for the film. On another woman, the turned-up collars, double-wrapped scarves, long sleeves, baggy pants and layers upon layers might look hopelessly goofy. (And, as we’ve seen through years of street paparazzi images of Keaton, her look can often be just that.) But from a costume perspective, Annie Hall, like so many of Allen’s films, is remarkable in how costume quietly defines each character without overwhelming other aspects of the film. Despite the fact that Annie’s outfits have become famous, we are not distracted by their presence; the quirky nature of the costumes perfectly suits Annie’s own quirky nature; every pairing is a seamless match. The very outrageousness of her clothing becomes a nuance, and the effect is, ultimately, surprisingly subtle.
Cinemode is OTDIF’s ongoing compilation of the world’s most stylish films, a must-see list for fans of fashion. From Klute to Breakfast at Tiffany’s to Shaft, some of the greatest style inspiration comes from the characters and costumes in film. Bookmark Cinemode and check back often to read the growing list. The reviews, written with an eye specifically toward fashion, are added to On This Day In Fashion on the anniversary of the film’s release date.