When Diane Keaton stepped out in a bowler hat, tie, starchy white shirt and boxy trousers in 1977’s Annie Hall, she created a menswear as womenswear fashion movement. The character of Annie Hall was written for Keaton – the quirky, affable actress who once dated Woody Allen. (In fact, she was sort of playing herself: Diane Hall is the actress’s real name, and her close friends have always called her Annie.) The tailored tomboy aesthetic that she debuted in the film became her trademark. Combined with an occasional string of pearls, a tuxedo jacket (with nary a blouse underneath), turtle neck, and a chunky wide belt, she’s stayed true to her signature look both on the red carpet and in her movies, proving for over thirty years that no one can pull off a button-down quite like she can.