The Rapper: Lil Wayne
What He Wore: Women's jeggings
WTF Was He Thinking? Back in 2011, Wayne was a big fan of skinny jeans. Super skinny jeans. But he took things to a whole new level when he decided that his skinny jeans weren't skinny enough and instead opted to wear a pair of women's jeggings during the 2011 MTV VMAs. How did he walk around in these things?
Photo Credit: New York Magazine