Diane Keaton (Annie Hall, 1977)(01 of11)
Open Image ModalDiane Keaton played Annie Hall in Woody Allen’s award-winning film of the same name, which won her an Academy Award for Best Actress in a Leading Role in 1977. By wearing suits, shirts, ties and oversized bowler hats throughout the majority of the film, Diane Keaton helped pioneer the androgynous look for a new era.
Mariel Hemingway (Manhattan, 1979)(02 of11)
Open Image Modal'Manhattan', the romantic comedy-drama, follows the story of the twice-divorced 42-year-old comedy writer’s (Woody Allen) love life, who before eventually falling in love with his best friend’s mistress (Diane Keaton) dates the 17-year-old, Tracy, as played by Mariel Hemingway. All through the black and white film Mariel Hemingway appears in simple classic fashion. Calvin Klein built an empire on less.
Mia Farrow - Purple Rose of Cairo (1985)(03 of11)
Open Image ModalMia Farrow styles a brown-scaled fashion with her iconic hat in 1985’s Purple Rose of Cairo, which fitted to the depressed times portrayed in the film. The story follows Mia Farrow in the leading role as Cecilia, who goes to the movies to escape her depressing life as a clumsy waitress in an abusive marriage.
Dianne Wiest (Hannah and Her Sisters, 1986)(04 of11)
Open Image ModalFor her role in 'Hannah and Her Sisters', Dianne Wiest received an Oscar for Best Actress in a Supporting Role in 1987. With the use of different brooches and pins, Dianne Wiest made her seemingly masculine brown-green scale blazers and jackets look feminine, and fashionably desirable.
Barbara Hershey (Hannah and Her Sisters, 1986)(05 of11)
Open Image ModalCompared to the style of Dianne Wiest in Hannah and Her Sisters, Barbara Hershey was far more understated, capturing a style of Everywoman with her coats, skirts and just a few carefully-added accessories.
Mira Sorvino (Mighty Aphrodite, 1995)(06 of11)
Open Image ModalAnother Academy Award, this time for Mira Sorvino in 1996 for her role as a prostitute and part-time adult star. Her character’s profession required a lot of latex and skin tight clothing including outrageous accessories, thus, an unimaginable star was born.
Julia Roberts (Everyone Says I Love You, 1996)(07 of11)
Open Image ModalIn this star-studded film, Julia Roberts shows off her beauty with natural makeup. Her stand out outfit is this yellow dress.
Julia-Louis Dreyfus (Deconstructing Harry, 1997)(08 of11)
Open Image ModalJulia-Louis Dreyfus is the lead female in 'Deconstructing Harry', as Leslie, a woman having an affair with her sister’s husband. Her beautiful black curls and mix of shirts and flowery skirts help create a feminine and ladylike look for an otherwise potentially unlikeable character, due to her indiscretions.
Melanie Griffith (Celebrity, 1998)(09 of11)
Open Image ModalIn this comedy-drama focusing on the different paths a couple take after a divorce, Melanie Griffith plays the glamorous Nicole Oliver, who ironically wears an innocent white dress while saying the memorable line, “I can't have sex with you! My body belongs to my husband and there is no way that I could betray him in that way. But what I do from the neck up is a different story”.
Penelope Cruz (Vicky Cristina Barcelona, 2008)(10 of11)
Open Image ModalPenelope Cruz’ portrayal of Maria Elena with messy hair and the vibrant personality made everyone fall in love with her, including her then co-star Javier Bardem, now her husband. Throughout the film Penelope Cruz makes a class act of the silky bohemian outfits classy with her dare-to-care attitude.
Scarlett Johansson (Match Point, 2005)(11 of11)
Open Image ModalScarlett Johansson played to her simple but seductive strengths in this mystery-drama, for which she was nominated for a Golden Globe. Appearing in small white dresses, often matching the tennis theme of the film, Scarlett Johansson proved, once again, that Woody Allen has always known just how to pitch his female characters...