Her lonely movie star in Notting Hill wouldn’t be quite the same without the beret and sunglasses she wears to hide from the paparazzi. To play opposite the male style icons Brad Pitt and George Clooney in Ocean’s 11, she adopted a sleek wardrobe of suits and mandarin collar jackets that worked with Tess Ocean’s curator backstory. Mona Lisa Smile’s earnest Wesleyan teacher called for 1950s prim skirts and cardigans, but with off-kilter add-ons that spoke to her rule-defying spirit.
In Erin Brockovich, turn from down-and-out single mom to fiery activist, Roberts’s outfits go from sultry (bustier tops and denim miniskirts)—to slightly less so (pink blazers and leather skirts).
For her most famous switcheroo, in Pretty Woman, Roberts trades thigh-high boots and crop tops for the sophistication of opera gloves and ruby necklaces gifted by her corporate raider beau. The power of presentation is further illustrated by the film’s revenge shopping scenes and the out-of-touch reactions of snooty salesgirls. As Vivian, Roberts’s clothes aided in the creation of a classic on-screen moment, and they also helped to make her a star. When you see a white dress with oversize shoulder pads and a wide-brim hat you can’t help but think, “Big mistake. Big. Huge,” as the star delivers the ultimate retail comeuppance and cements herself as a fashion icon for the ages.