A History of Stylish Celebrities Wearing Terrible Outfits Image via Getty / WireImage / Bennett Raglin

Jay Z

Where: MTV Video Music Awards official after party
When: Sept. 13, 2009

Lil Mama crashing Jay Z and Alicia Keys' performance at the 2009 MTV VMAs wasn't even the craziest thing at the award show. What was? Truthfully, It might be Hov's denim on denim look with the brown leather vest, which he also wore to the after party. Womp womp.

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