Love Story (1970)
Jennifer Cavalleri may have died at the end, but Ali McGraw's preppy look with a touch of bohemia—peacoat, shirtdresses, turtlenecks, miniskirts and tights—lives on. The famous knit hat, which became an instant trend, was the actress's own, and the rest of the Ivy League pieces have continued to look fresh for decades.
Rear Window (1954)
Costume designer Edith Head won a well-deserved Oscar for the five stunning outfits—marked by sweeping skirts, fitted bodices and ladylike, elbow-length gloves—that Grace Kelly wears in this Hitchcock thriller. Along with two other films the master of suspense made around the same time, "Dial M for Murder" and "To Catch a Thief," it confirms Kelly's image as the epitome of '50s elegance.
Bonnie and Clyde (1967)
It may have been set during the Great Depression, but Faye Dunaway's Bonnie Parker has a badass '60s vibe that gives her timeless style and sex appeal. With her skinny pencil skirts and trademark beret, she made a lasting impact on the fashion world. Almost a half-century later, fashion magazines are still doing shoots with a Bonnie and Clyde theme.
Breakfast at Tiffany’s (1961)
Audrey Hepburn wears seven outfits in this confection of a movie—all of them standouts in the annals of fashion. The film was ground zero for such enduring wardrobe staples as ankle pants, oversize sunglasses, exquisitely tailored wool coats and—most important—the little black dress. The one in "Breakfast at Tiffany's," designed by Hubert de Givenchy, has been called the most iconic apparel item of the 20th century.
Desperately Seeking Susan (1985)
Susan Seidelman initially considered Goldie Hawn but took a chance on a budding pop singer who'd never appeared in a movie—Madonna—largely because she had the style the director wanted for the title role in this comedy-drama. Think wild hair and headbands, studded boots, harem pants, eyelinered beauty marks and funky costume jewelry. The film was well received, but we remember that look even better.
Jean-Luc Godard's "Breathless" introduced Jean Seberg as an American expat with a carefree pixie haircut, striking black eyeliner and a wardrobe based on chinos and boatneck Bretons with horizontal navy stripes—a look of Parisian nonchalance that lingers even today. Both Seberg and co-star Jean-Paul Belmondo wore their own clothes to suit their characters, at the director's encouragement.
Working Girl (1988)
Tess McGill (Melanie Griffith), who commutes from Staten Island to Wall Street to work as a secretary, has a wardrobe that reflects her origins and ambition. The oversize earrings, big hair and bigger shoulder pads look dated now, but any glance at a #TBT post on Facebook reveals that we all did it. Then Tess' boss (Sigourney Weaver) advises her to "rethink the jewelry," and the result is an '80s Cinderella story.
Mildred Pierce (1945)
Joan Crawford refused to wear the off-the-rack wardrobe director Michael Curtiz had in mind for her when she played the title role in "Mildred Pierce." Instead, she commanded her personal dressmaker to nip in the bodices and fill out the shoulders to create her signature wasp-waisted style. Curtiz reportedly complained to Jack Warner: "She comes over here with her high-hat airs and her goddamn shoulder pads ..." Still, she won an Oscar.
Rosemary's Baby (1968)
Famous for her long tresses when she was on "Peyton Place," Mia Farrow made a major style statement with her new pixie bob in "Rosemary's Baby." Vidal Sassoon was widely credited with the look, but Farrow recently revealed that she had cut her own hair with fingernail scissors. Despite rumors that Frank Sinatra hated the pixie cut, she says he loved it (though his ex-wife Ava Gardner commented, "I always knew Frank would end up in bed with a boy").
Key Largo (1948)
Four years after her debut as a femme fatale in "To Have and Have Not," Lauren Bacall once again was cast opposite Humphrey Bogart, but this time she played a young widow in a perfectly fitted white dress shirt. In fact, that signature shirt—complementing a full wool skirt with a wide-buckle belt and espadrilles—is the only one she wears throughout the film.
As mobster Sam "Ace" Rothstein, Robert De Niro gets to wear some gorgeous, if flashy, duds, but it's Sharon Stone's trophy wife Ginger who has the most fashion fun in this Martin Scorsese crime epic. The slinky dresses, the furs, the bling—they define her character. And who could forget that closet when she's packing up to leave?
Anticipating the "athleisure" craze by more than 30 years, Jennifer Beals spends a lot of time showcasing her perfectly toned bod in leggings and Lycra. The ripped, off-the-shoulder gray cotton sweatshirt she wears in the film may have been inspired by designer Norma Kamali, who produced a jersey fleece collection in 1980—the first time the activewear fabric appeared on the catwalk.
The Philadelphia Story (1940)
You could take Tracy Lord's camp shirt, trousers and sandals right off her and wear them today without looking dated in the least. But the character played by Katharine Hepburn cleaned up nicely too, in the goddess-style gown and dance frock designed by Adrian. Hepburn's take on her groundbreaking role in fashion: "I just had good timing. The pants came in, the low heels came in, the terrible woman came in, who spoke her mind."
Annie Hall (1977)
Woody Allen says his costume designer hated what would become the Annie Hall look. Diane Keaton came in, he recalled, "and the costume lady on 'Annie Hall' said, 'Tell her not to wear that. She can't wear that. It's so crazy.' And I said, 'Leave her. She's a genius. Let's just leave her alone, let her wear what she wants.'" The director was right: Keaton took the menswear look to the next level simply by wearing clothes she wore in real life.
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