How to Dress Like Woody Allen's Leading Ladies

Whether the women in Allen's films are portrayed as neurotic or naive—confident or confused—they endure as strong female personalities onscreen—with a unique sense of style to match. From Annie Hall to Vicky Cristina Barcelona, here’s how to wear your favorite Woody Allen character's signature style.
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Whether the women in Allen's films are portrayed as neurotic or naive—confident or confused—they endure as strong female personalities onscreen—with a unique sense of style to match. From Annie Hall to Vicky Cristina Barcelona, here’s how to wear your favorite Woody Allen character's signature style.
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From the charmingly naive Annie Hall to the aging alcoholic Broadway star Helen Sinclair, Woody Allen certainly has a knack for creating complicated multi-dimensional female characters.

His latest film, Blue Jasmine (which comes out today), introduces us to Jasmine, played by Cate Blanchett. She's a disgraced New York socialite who, after discovering her husband (played by Alec Baldwin) to be a philanderer and a crook, is forced to move from her luxurious Upper East Side home to her sister's "homey" San Francisco apartment.

"People criticized me for being a self-hating Jew, that’s come up. But not being able to create good women was not aimed at me very often," so says Allen in a recent interview with the New York Times. Whether the women in Allen's films are portrayed as neurotic or naive, confident or confused, they endure as strong female personalities onscreen--with a unique sense of style to match.

From Annie Hall to Vicky Cristina Barcelona, here’s how to wear your favorite Woody Allen character's signature style.

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Diane Keaton in Annie Hall

When Annie Hall came out in a men's button down shirt and tie, a black hat, very loose khakis, and a Ralph Lauren tuxedo vest after her tennis match with Alvy, the fashion world quickly followed suit. The movie's costume designer Ruth Morley worked with Diane Keaton to create her character's iconic look--which was based on the actress's own personal style.

Shirt: J. Crew, $69.50 Vest: Yves Saint Laurent, $395.01 Tie: Brooks Brothers, $79.50 Hat: Goorin Bros., $130 Shorts: Uniqlo, $29.90 Shoes: Reed Krakoff, $625

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Shelley Duvall in Annie Hall

While Duvall will always be most known for her role as Wendy Torrance in The Shining, there's just something special about her as a Dylan-worshipping hippie chick whose vocabulary consists of made-up words like "transplendent."

Sunglasses: The Row, $199 Dress: Marni, $475.00 Bag: Bottega Veneta, $2,000 Shoes: Ancient Greek Sandals, $138.75

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Meryl Streep in Manhattan

Jill Davis is one of Meryl Streep's sexiest roles in film. She leaves her husband Isaac for a woman named Connie after engaging in a threesome with them, and then continues to publish a tell-all book about her marriage with him.

Dress: Uniqlo, $69.90 Necklace: BaubleBar, $36 Bag: Saint Laurent, $2,858.70 Shoes: Christian Louboutin, $795

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Mariel Hemingway in Manhattan

Hemingway plays Tracy, a 17-year-old Dalton student who shows sophistication beyond her years in her illicit relationship with Allen's twice-divorced 42-year-old character Isaac. Only 16 during filming, Hemingway's performance earned her an Oscar nomination for Best Supporting Actress.

Hair Ties: Emi-Jay, $6.50 Cardigan: Club Monaco, $139.50 Skirt: ModCloth, $57.99 Shoes: Salvatore Ferragamo, $450

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Mia Farrow in The Purple Rose of Cairo

Farrow's sweet and hopeless romantic Cecilia escapes from the harsh realities of the Depression and living with an unloving husband by entering the world of her favorite movie.

Dress: ModCloth, $84.99 Hat: Stella McCartney, $225 Bag: Burberry, $1,195 Shoes: Chloé, $670

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Dianne Wiest in Hannah and Her Sisters

Wiest's role as Hannah's messy sister Holly won her a number of awards, including an Oscar for Best Supporting Actress. Holly's mind is as unpredictable as her uncoordinated outfits—which she isn't shy about over-accessorizing with brooches.

Vest: Jean Paul Gaultier, $325 Dress: ModCloth, $79.99 Hat: Ralph Lauren, $48 Brooch: Bijoux de famille, $304

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Dianne Wiest in Bullets Over Broadway

Wiest reunited with Allen in 1994 for another award-winning performance as the fading Broadway starlet, Helen Sinclair. Helen is every bit the diva she believes herself to be—and she makes sure she dresses the part, too.

Dress: Etro, $1,190 Headband: Nasty Gal, $30 Bag: Halston Heritage, $97.50 Shoes: Dolce & Gabbana, $745

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Scarlett Johansson in Match Point

Johansson is the struggling American actress Nola Rice who pursues a doomed affair with retired tennis player Chris Wilton (played by Jonathan Rhys Meyers). I had quite the little white tennis dress obsession after seeing the movie.

Dress: alice + olivia, $237.60 Necklace: Givenchy, $31.90 Shoes: ASOS, $54.30

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Penélope Cruz in Vicky Cristina Barcelona

Cruz plays the wildly passionate ex-wife Maria Elena that Javier Bardem's character, Juan Antonio, just can't seem to quit. She oscillates between being fiercely empowered and cripplingly dependent--and her instability is reflected in her outfits.

Hat: Borsalino, $357 Dress: Haute Hippie, $441 Bag: Prada, $2,500 Shoes: Nina Ricci, $324.12