A History of Stylish Celebrities Wearing Terrible Outfits Image via Getty / FilmMagic / Jeff Kravitz

Kanye West

Where: Grammy Awards
When: Feb. 8, 2006

We can appreciate the fact that Kanye West has always had his own sense of style—remember when he wore Ralph Lauren while other rappers rocked baggy jeans? But with that said, even his good track record can't save the white suit and taco meat outfit—one of the worst hip-hop fashion fails we've seen—he wore to the Grammys. He would've benefited from a few more buttons, or some manscaping. 

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