2. Annie Hall – Costume designer Ruth Morley

Annie Hall

Diane Keaton as Annie Hall

We bet Woody Allen would be surprised to find one of his movies on a list of fashion films, but it’s thanks to the divine Diane Keaton that Annie Hall makes the cut. It is clear that she brought her personal style to this now classic, if not initially unorthodox, love story. And it’s Woody’s (and costume designer Ruth Morley’s) genius in giving her room to do so that has made it one very fashionable film.