Since its premiere 35 years ago, on March 23, 1990, Pretty Woman has earned its place in cinematic history, partly thanks to its enduring rags-to-riches love story and iconic wardrobe. The Golden Globe -nominated film — directed by the late Garry Marshall — follows sex worker Vivian Ward ( Julia Roberts , in an Oscar -nominated performance) and wealthy entrepreneur Edward Lewis ( Richard Gere ). After a chance encounter on Hollywood Boulevard when Edward stops to ask for directions, the corporate raider hires the street-smart Vivian to spend the night with him at his hotel, which ultimately turns into a week.
Along the journey, Vivian evolves not only in her way of thinking but also in her fashion, including when viewers first meet her in a midriff-baring, one-piece tank dress to the final scene of her sporting a classic black blazer and white T-shirt. In 2024, five-time PEOPLE's Most Beautiful Woman recipient Roberts told British Vogue about her collaboration with the film's costume designer, Marilyn Vance. "I remember her to be very caring about how I felt in the clothes," Roberts recalled.
"I'm not really comfortable wearing such bare things, and she was very mindful and respectful of that." Though not every ensemble made us swoon, Roberts' looks in the rom-com captured viewers' hearts and transcended time and trends. Here's the ultimate ranking of every memorable (plus that one big mistake !) outfit the actress wore in Pretty Woman .
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