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9 Vivian Ward (Julia Roberts) Pretty Woman (1990)

The achievement of this film is that even Vivian’s trashy hooker clothes look almost wearable (admit it — she nearly convinced you that thigh-high boots could work as a look), and her classic bombshell makeover is downright gorgeous, albeit in a sometimes rather early ’90s way. But she gets away with the culottes and looks great in polka dots, and the one-two punch of that red evening dress with the heart-shaped rubies and the little black number earn her a place on the list.

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