The Rapper: Jaden Smith
The Women's Clothing He Wore: Like Lil Wayne, Will Smith's son wore a pair of women's pants during a performance at the Grammy Awards back in February 2011.
How Ridiculous Did It Look? Because Jaden Smith isn't as popular as Wayne, his pants didn't get quite as much attention as Wayne's later did. But his pants did inspire the Washington Post to write a story about how many male performers, including Justin Bieber, were turning to women's pants back in 2011. "I've worn women's jeans before because they fit me better," Bieber said at the time. "I just think that whatever works, works."
Photo Credit: AP