Movie Poster for the film Annie Hall from 1977. Photo via DVDBeaver.com.
April 20, 1977 upon the release of Woody Allen's film.
Kate Moss, Mary-Kate Olsen, Ralph Lauren, Brooke Shields, Jennifer Aniston
The brainchild of filmmaker Woody Allen, Annie Hall is the title character in his 1977 film by the same name. She's a dreamy, blundering singer and photographer played by Diane Keaton (for which Keaton won an Oscar) who struggles through her relationship with the neurotic comedian Alvy Singer, played by Allen himself.
Through her sweet but bold androgynous style choices, Annie epitomizes the timid trendsetter. She is always remembered in her slouchy khakis, fitted collared blouse and men's tie and vest, casual but comfortable with a confident ease. One hand hooks in her pocket while she occasionally holds her fedora in the other, and her hair hangs loosely undone.
Annie Hall: Sometimes I ask myself how I'd stand up under torture.
Alvy Singer: You? You kiddin'? If the Gestapo would take away your Bloomingdale's charge card, you'd tell 'em everything.
- Annie Hall screenplay
Annie Hall movie poster.
You can always go too far, as Annie has done on this film poster. The loose, easygoing style that she achieves at some points in the film occasionally plummets into layers of heavy clothes with no shape or character. If you can't tell how many skirts she's wearing, then there is a problem.
Before there were women wearing suits at the Oscars, there was Annie Hall. Even Diane Keaton has stuck with the menswear look after the film and throughout her whole life. Every time that Kate Moss wears a tiny black vest or Avril Lavigne wraps a tie around her neck, Annie Hall is there in spirit.
Moss tries the Annie Hall look.
Get the Look.
If you're feeling inspired, steal one of your boyfriend's ties. Stores like H&M now carry vests like Annie's, which look great over a white button-up. For a modern look (and to show a little leg), try pairing the look with loose shorts instead of pants, like Kate Moss.