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InStyle: The Riskiest Golden Globes Looks Ever

Julia Roberts, 1990

Up-and-comer Julia Roberts flipped the script for her "Steel Magnolias" Globes win. After browsing the Giorgio Armani atelier with then-beau Kiefer Sutherland, she opted for an oversize men's suit. According to employees of the designer, Roberts was determined to have an outfit as comfortable as her boyfriend's.

(CREDIT: Ron Galella, Ltd./WireImage)
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