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Princess Diana, who dressed with intention and understood the power of telling a story through a visual, had succeeded in her task

Campus DJ Usher in a fedora, Cook in the chicest of prom dresses, Prinze Jr clad in varsity bomber jackets Cruel Intentions (1999) Cruel Intentions s Kathryn Merteuil (Sarah Michelle Gellar) established herself as one of the decades most infamous on-screen antagonists thanks to her Machiavellian scheming and whip-smart fashion sense

Look for a dress with contrasting shapes - tight up top, and full of volume below - for a more dramatic silhouette

(Photo by Ron Adar / SOPA Images/Sipa USA) Captions are provided by our contributors