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Gone With the Wind (1939)
We're not condoning the way this movie romanticizes slavery or the Old South, of course. But we can acknowledge the impact of the breathtaking 5,500 wardrobe items, including 40 outfits for Scarlett O'Hara, which Walter Plunkett designed for the film. Each piece of O'Hara's — from her demure picnic dresses to the emerald green curtains repurposed into a defiant look of survival — serve to illustrate her character's mood and position in society. Nope, we're not longing for those corsets or the "Mammy" to cinch them for us; we just can't take our eyes off that burgundy gown on Vivien Leigh.
Watch Gone with the Wind on YouTube.
Funny Face (1957)
Before there was The Devil Wears Prada, there was a nerdy bookstore clerk (Audrey Hepburn) accidentally discovered by a magazine editor (Kay Thompson) and a photographer (Fred Astaire), and whisked off to Paris, where she really just wants to meet a philosopher she idolizes. Costume legend Edith Head and Hubert de Givenchy make a very good case for the artistic value of fashion, most memorably with Hepburn's combo of a hip black turtleneck, black pants, white socks, and loafers.
Watch Funny Face on Amazon.
Here's another American in Paris, this time played by Jean Seberg, whose chill expat look, complete with an enviably flattering pixie cut, has inspired generations of copycats. Director Jean-Luc Godard didn't hire a costume designer for the film — about a criminal (Jean-Paul Belmondo) on the run who shacks up with an American girl who sells newspapers for a living — and the presumption is that the actors supplied their own clothing. If that's true, let us please go back in time and raid Seberg's closet for those striped dresses, sailor shirts, and pleated skirts.
Watch Breathless on Hulu.
Breakfast at Tiffany's (1961)
We're not just talking about the ankle-length LBD Givenchy specially designed for Audrey Hepburn for the film. Every scene features a Givenchy outfit we'd kill for — the shorter black dress paired with a wide-brimmed hat, that orange coat, the pink rhinestone party dress, and even her casual cowl-neck sweater paired with cigarette pants. Also, don't forget how Patricia Neal's outfits make you want to grow up and be a glamorous sugar mama.
Watch Breakfast at Tiffany's on Netflix.
The Great Gatsby (1974 & 2013)
The roaring '20s are so idolized by fashion designers and amateurs alike, you know these two adaptations of Fitzgerald's classic faced a lot of pressure to get the costumes just right. The 1974 version saw Mia Farrow in gauzy, dreamlike gowns to match her noncommittal character, while Robert Redford and company impressed in their Ralph Lauren suits, earning costume designer Theoni V. Aldredge an Oscar despite the film's poor reception. In 2013, Baz Luhrmann enlisted his Oscar-winning wife Catherine Martin for costume duties, and she decided not to take the '20s setting too literally. With the help of Miuccia Prada, she added a bit more body-conscious sex appeal (okay, boobs) to the androgynous styles of the era, and took inspiration from vintage fashion sketches to alter Prada and Miu Miu designs. The results are swoon-worthy, and again nabbed the Oscar.
Watch the 1974 Great Gatsby on Netflix, and the 2013 version on Amazon.