On of my all time favorite movies is Woody Allen’s Annie Hall and have watched it twice in two weeks thanks to it being on one of my movie channels. A story about a neurotic New Yorker (of course, played by Allen) and his love affair with the kooky Annie Hall. I can’t help but see some of myself in her character, and know many other women feel the same. While some credit goes to the male writers for tapping into the female psyche, most goes to Diane Keaton, who is absolutely wonderful in the role that won her an Oscar. While I can see myself in her character, what I would really love to see myself in is the clothing she wears throughout the movie. The bohemian urban hippie looks she wears in some scenes are great, but the looks that really steal the show- and started a fashion phenomenon- are her menswear inspired ensembles. If you’ve seen anything of Diane Keaton’s sartorial choices throughout the years, it should come as no surprise that the clothes Annie wears are all Keaton’s own. Of course, this look isn’t the easiest to pull off. The above outfit looks great on Keaton, who is tall and lean, but put those pants on my 5′1″ frame and it won’t be a pretty picture.

To make the Annie Hall look work for me, I’m thinking cropped pants like these from Lauren Moffatt.

This short sleeved white shirt from James Perse.

A thin tie-dye scarf, like this one from TDM, is a funkier, less Avril Levigne, option than a tie.

Last but not least, a low-cut, cropped vest from Ann Taylor is the finishing touch.