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1. Cher in Bob Mackie (1988 Oscars): When we think of unforgettable red carpet moments, Cher and Bob Mackie instantly come to mind, as their collaborations are forever etched in fashion history.

The duality influenced his approach to clothes, as he mixed hard masculine shapes with soft and sheer textures or looked to blend classic tailoring archetypes with his athletic wear roots.

The bottom half of the dress was marked by a cascade of sheer, petal-like strips that shifted with Meester’s every step. It was an elevated, romantic way to do florals for the spring and summer ...