'Annie Hall'

"I love what you're wearing," neurotic Alvy Singer says to kooky Annie Hall in the breakthrough 1977 Woody Allen movie that launched a generation of cross-dressers. Diane Keaton -- in oversized khakis with a black vest and blue necktie -- made full-on androgyny a chic alternative to the era's fixation on form-fitting disco wear and polyester pantsuits. Sure, ladies had borrowed from their brothers' and beaus' closets in the past. But filching the whole outfit? A first.<br>
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The story goes that Keaton showed up on the set wearing her own haberdashery, and costume designer Ruth Morley said: "Too crazy." But Allen appreciated the unstudied look and, in the end, Ralph Lauren contributed key pieces. "The biggest fashion moments aren't contrived," says Patricia King Hanson of the American Film Institute. "It worked and made such an impact because it felt natural." What also worked was Hall's undeniable sex appeal in clothes that made her as shapely as a pup tent. Those ultra-tight Jordache jeans got shelved and that, alone, was liberating.<br>
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( Los Angeles Times )

"I love what you're wearing," neurotic Alvy Singer says to kooky Annie Hall in the breakthrough 1977 Woody Allen movie that launched a generation of cross-dressers. Diane Keaton -- in oversized khakis with a black vest and blue necktie -- made full-on androgyny a chic alternative to the era's fixation on form-fitting disco wear and polyester pantsuits. Sure, ladies had borrowed from their brothers' and beaus' closets in the past. But filching the whole outfit? A first.

The story goes that Keaton showed up on the set wearing her own haberdashery, and costume designer Ruth Morley said: "Too crazy." But Allen appreciated the unstudied look and, in the end, Ralph Lauren contributed key pieces. "The biggest fashion moments aren't contrived," says Patricia King Hanson of the American Film Institute. "It worked and made such an impact because it felt natural." What also worked was Hall's undeniable sex appeal in clothes that made her as shapely as a pup tent. Those ultra-tight Jordache jeans got shelved and that, alone, was liberating.

More in Image:
10 classic style movies | Photos
Scene Stealers: Movie costumes that started fashion trends
Style films that packed a punch? Insiders' favorites
Your turn: Share your favorites on our blog

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