How to dress like Annie Hall

How to dress like Annie Hall thumbnail
Annie Hall wore a man's necktie along with other menswear

Annie Hall was the free-associating, WASPy, menswear-borrowing girlfriend of director Woody Allen's alter-ego character, Alvy Singer, in the 1977 movie named after her. The movie won an Academy Award for Best Picture, the last comedy to do so until "Shakespeare In Love" won in 1998. The character of Annie as played by Woody Allen's then real-life girlfriend, actress Diane Keaton, launched a small revolution in women's fashion in the U.S. and elsewhere. It changed both the focus and the dimensions of women's clothing, especially suits, and its feeling still resonates in American women's sportswear in 2010.

Things You'll Need

  • Man's necktie
  • Vest
  • Men's Oxford shirt
  • Oxford shoes
  • Fedora
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Instructions

    • 1

      Put on a man's shirt and tie. After "Annie Hall," American women and models wearing neckties have been a fashion fixture every few years and have never totally gone out of style. One famously iconic image of Annie is her first meeting with Alvy in the lobby of a sports club. He's charmed and flummoxed by what she's wearing; it almost looks like she's borrowed her brother's clothes. The top is not crispy and ironed, but seems as if she just picked it up off the floor and threw it on. Casual is key to the Annie Look, and to the character. Alvy thought she just had things effortlessly: charm, entitlement, style.

    • 2

      Add a man's vest, or one that looks like a man's. But don't make it match too closely. Annie always looked clean, fresh and winsome, but a little mismatched, as though she dressed while she was thinking of something else. She also blended different neutral colors and the textures of her garments in unexpected ways.

    • 3

      Buy bigger. Annie's look was always oversized, except for one or two pieces. In the scene mentioned earlier, she's almost swimming in her clothes. Still, there's an art to it -- the outfit has a distinct shape even though it's large, and many of the pieces have distinctive structure. Let your shoes fit, though -- Annie was nothing if not comfortable.

    • 4

      Throw on a hat. Annie wears a large fedora with the brim turned back in that pivotal meeting scene. She always wears a lot of pieces of clothing. Diane Keaton wore many of her own clothes in the film, against the costumer's stringent objections, so Annie's style was really Keaton's own. The costumer felt that Keaton wore too many things at one time and that she "looked crazy." Woody Allen reportedly said she was a genius and to "leave her alone."

    • 5

      Overdo it. Add one piece too many, pushing the overall outfit closer to costume than to everyday wear.

    • 6

      Rumple and layer. Annie's clothing is usually a little wrinkled, and the mannish blazer over a flouncy skirt, hinting vaguely at a pioneer look, was her invention. It lasted well into the '80s and resurrected for a while in the '90s in a slightly more tailored version. Add a pair of men's-look flat oxfords or cowboy boots to complete the look.

    • 7

      Add a feminine touch -- a lock of hair pulled out, a romantic accessory. For all her menswear, Annie's goofy girliness and vulnerability were her greatest charm, even as she grew more sophisticated over the story arc of the movie. She made the woman underneath all the layers of cover irresistible to Alvy. The Annie Look is quintessentially about a woman who doesn't have to resort to conventionally sexy clothing to convey artfulness and a sensual originality.

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References

  • Photo Credit shirt and tie image by Christopher Hall from Fotolia.com

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