Where: MTV Video Music Awards

When: 2008

Lupe's outfit was a fiasco, from the vest to the riding jodhpurs. And we can't forget about the OJ Simpson glove. The rapper told Miss Info that he planned on debuting his Fall of Rome line on the red carpet but was instead forced to go to plan B after the garments didn't make it through customs. Plan B was this look by a Belgian label called Les Hommes. In the words of Miss Info, "that which looks awesome in a Men’s Vogue editorial spread set in the French countryside….doesn’t always translate in real life."