The look for the Annie Hall character in this film of the same name was all Diane Keaton’s doing. In fact, the “menswear-on-women” look, or what we presently call the “boyfriend” look, is what the actress regularly fashioned in her real life. Not that that typically has an impact on the folks making the film. But in this case Diane was also a good friend of writer/producer/director/co-star Woody Allen, and he loved the look, refusing to let the film’s costumer dress her. The style is both modest and neurotic, perfectly fitting the movie’s quirky character.
Ralph Lauren finessed the look in the year that followed, and Donna Karan played with it in her fashion line while working at Anne Klein. Others soon followed suit.