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Worn three years after her separation from the then-Prince Charles, Diana broke Royal protocol by stepping out at a Vanity Fair party in the off-the-shoulder, form-fitting, black silk mini dress
Photographed out in New York City, Iman tapped into one of the 90s other biggest trends underwear as outerwear
Here's what to think about: Your dress's structure makes a big difference - some dresses come with built-in support, while others need more help from undergarments
Ewell now rates only a footnote in cinematic history, while Monroe's subway grate scene became one of the most recognizable images in modern society
