A few weekends ago I had the pleasure of watching To Rome With Love, Woody Allen's latest effort in his quest to make a film in every country in the European continent. It was a charming film that heralded a return to the filmmaker's absurdist beginnings, focusing on four separate - but equally bizarre - vignettes set in the eternal city. There were a few things I couldn't get over: (1) Penelope Cruz is gorgeous no matter what, even when playing a brash call girl, (2) the idea that Jesse Eisenberg will grow up to be Alec Baldwin is an interesting notion that I will continue to entertain, (3) Ellen Page, the femme fatale in Eisenberg's life, wore some fantastically comfy-looking clothes. Ellen's wardrobe spurred me to create a list that I've been wanting to put together for ages but never got around to doing: the most stylish characters in Woody Allen's filmography. It's no coincidence that all of the characters that make this list are female. While the actor-director and his band of Woody wannabes (Owen Wilson and John Cusack are notable for their Allen-esque performances in his films) have styles that run the gamut from schlubby to nondescript on screen, the term 'chic' is rarely ever applied to them. (That being said, I do think Jeff Daniels looks absolutely dashing in The Purple Rose of Cairo, but he doesn't compete with Mia). These are just my top ten favorite fashion stars from Woody's films, so obviously a lot of great women aren't up here. If you have a fave look that isn't on the list, tell me below in the comments. 
1. Annie Hall (Diane Keaton), Annie Hall
No list of Woody Allen characters, fashion or otherwise, would be complete without a place for Annie Hall, the lead character of Allen's legendary film of the same name. The Annie Hall look became a very distictive trend in the late 1970s, consisting of slouchy blazers paired with vests, maxi skirts, billowy pants, neck ties and boots. My mother was a devoted fan of the Annie Hall look (which actually was Keaton's real life look - everything she wore in the film came from her own closet) and I have inherited many fantastic oversized blazers and calf-length pleated skirts because of it. 
2. Cecilia (Mia Farrow), The Purple Rose of CairoThe Depression-era fashion that Farrow wears in the film is anything but depressing. I really adore this film and I think that this is the best Mia Farrow ever was in a Woody Allen film. People who have seen Purple Rose might prefer the Art Deco-inspired fashion from the film-within-the-film, but I personally can't resist the felt hats and collared dresses that Cecilia wears. 
3. Helen Sinclair (Dianne West), Bullets Over BroadwayAs fading stage actress Helen Sinclair, Dianne West has a look that is as big as her diva character's ego. Decked out in the best of 1920s fashions, Helen is an interesting counterpoint to Mia's look in Purple Rose, as well as the girls from Woody's later film Midnight in Paris. Helen is bright, sparkling and fabulous - everything a star should be. 
4. Maria Elena (Penelope Cruz), Vicky Cristina BarcelonaMaria Elena is one of Woody Allen's most unique - and certainly best dressed - characters. When she arrives in Barcelona, Maria Elena just has a few bags with her. But there are so many gems in her apparently limited (but seemingly endless) wardrobe. In ivory lace, printed pants, bowler hats and scoopneck dresses, she is pure bohemian. 
5. Nola Rice (Scarlett Johansson), Match Point"That. White. Dress." That's pretty much all I heard about Match Point when it first came out in '05. Scarlett's debut in the film in that wrap-front dress was like the second coming of Marilyn Monroe right out of The Seven Year Itch. Nola keeps it pretty wholesome the rest of the film (style-wise, that is) in tailored denim and button-downs.  
6. Adriana (Marion Cotillard), Midnight in ParisDuring the day, Gil (Owen Wilson) was contented by Ines (Rachel McAdams), his chicly-dressed by naggingly bitchy fiancée. But by night he romanced Adriana, the beautiful muse to pretty much every artist during the 1920s. Always decked out in a gorgeous beaded frock, Adriana embodies the flapper look (even though she much preferred La Belle Époque). 
7. Linda (Mira Sorvino), Mighty AphroditeI think Linda's look here is really a lot of fun. There are several moments where her style reminds me of a grown-up Iris from Taxi Driver (especially in her hot pants and thigh-high boots). Granted, they were both prostitutes, but I think the comparison stands even without their belonging to the same profession. Mira Sorvino has the honor of having been one of Allen's most colorfully and wildly dressed characters, because, you know, winning the Oscar isn't honor enough. 
8. Monica (Ellen Page), To Rome With Love Page's Monica has that loose comfy-chic that Vicky and Cristina had in Barcelona. Her character's look has its origins in the loose style of Mariel Hemingway's Tracy in Manhattan, as well as Hannah and all of her sisters. I dig this look because it's comfy and cool at the same time, a hallmark of a truly stylish Woody Allen woman. 
9. Ellie (Téa Leoni), Hollywood EndingThe role of the studio-exec ex-wife of a neurotic film director suffering from hysterical blindness doesn't sound like the chicest of roles that an actor can take, but Téa Leoni had wonderful style in Hollywood Ending. In wide-legged trousers and sharp blazers, she looked quite reminiscent of Katharine Hepburn. 
10. Laura Kensington (Charlize Theron), The Curse of the Jade Scorpion Smoking cigarettes, flashing Woody Allen and looking completely Veronica Lake-esque in her tight white dress, trench coat and peekaboo curls, Charlize stole Scorpion from the whole rest of the cast. Her role as Laura Kensington is the most glamorous of any role that a woman has had in a Woody Allen film.