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8½ (1963)
Fellini's timeless ode to Italian style was as glamorous as it was sexy—all hourglass curves and heels.
Annie Hall (1977)
In baggy trousers, a fitted vest, and a wide tie, Diane Keaton spun menswear in an irresistibly quirky—and widely imitated—way.
The Birds (1963)
Alfred Hitchcock gave us plenty of impossibly feminine leading ladies, but Tippi Hedren, in knee-grazing skirts and bracelet-sleeved jackets, was one of his best.
Blow-Up (1966)
This movie's poster alone will make you want to dress like a swinging '60s model.
Clueless (1995)
Miniskirts and schoolgirl plaids captured the mood of the era, especially when worn with the confidence of Alicia Silverstone.
Desperately Seeking Susan (1985)
Madonna created an aesthetic with mesh tops, lacy underthings, and piles of gold jewelry, distilling the essence of the '80s East Village.
Eyes of Laura Mars (1978)
Though Faye Dunaway hit sartorial high points in Network and Bonnie and Clyde too, it was here, playing a fashion photographer, that she achieved style perfection.
Flashdance (1983)
Birthplace of the off-the-shoulder sweatshirt: It made girls across America take the scissors to their workout wear.
Funny Face (1957)
Few outfits have ever looked as simply elegant as a black turtleneck and cropped pants did on Audrey Hepburn.
The Great Gatsby (1974)
American classic: wispy beaded dresses and white sweaters—no surprise, considering Ralph Lauren had a hand in the costumes.
Love Story (1970)
Collegiate style got the attention it deserved, with peacoats and turtlenecks feeling suddenly, ineffably chic.
Mahogany (1975)
In the hands of Diana Ross, the wide-brimmed hat became the ultimate attention-grabbing accessory.
Mildred Pierce (1945)
Don't-mess-with-me sophistication (plus red lips, plush furs, and major shoulder pads) as only Joan Crawford could pull off.
Out of Africa (1985)
Meryl Streep turned the safari look into a full-on fashion statement, somehow appearing ladylike and rugged at the same time.
Saturday Night Fever (1977)
The white suit got all the notice, but we were—and remain—far more interested in the floaty, slinky, disco-era dresses.
Shampoo (1975)
The height of glam, with Goldie Hawn and Julie Christie in high-waisted pants and, naturally, totally amazing hair.
Unzipped (1995)
When Isaac Mizrahi let us into his world—complete with Linda, Cindy, Naomi, and Kate—we never wanted to leave.