Even though one of them is fictional, the three women that come to your mind first, when I mention women who look sexy in menswear, are probably Marlene Dietrich, Katharine Hepburn, and Annie Hall. You may also have thought of Lady Gaga, but I don't mean women in drag; I mean women who look like the sexy women that they are while wearing a suit.
It's a testament to her style that Annie Hall can hold her own next to such icons as Dietrich and Hepburn. And it's a testament to Diane Keaton, because, after all, there's a lot of Keaton in Hall.
Like last month's Fictional Fashion Icon, Alex from Flashdance, Annie Hall has had a huge influence on fashion, and Annie's almost timeless style remains relevant decades after it first made a splash. Her neutral color palette, baggy-and-cinched silhouettes, and whimsically sexy take on menswear continues to inspire generation after generation of fashion-loving movie viewers.
Yes, the late '70s was a magical time for fashion, and almost everyone looked pretty awesome -- I mean, Woody Allen's outfits in the film are pretty fantastic too -- but Annie's style is a cut above you average '70s-chic ensemble. She has a unique point of view and she's not afraid to dress differently than everyone else.
And it's her signature pieces that endure: her vests, her wide-brimed hats, her scarves, her amber-tinted glasses, and the way she layers spaghetti-strap camisoles and dresses over t-shirts.