6. Paris Hilton at the 2009 Grammys
Paris Hilton [via]
Not that Paris Hilton is or has ever been known as classy a gal with good taste and fashion sense, but this has to be among the worst. And that's saying a lot considering the endless supply of heinous outfits she's paraded down red carpets over the years. Just because it fits (barely) and is made by Versace doesn't mean you should wear it. Especially if it looks like you stole it from an 8-year-old figure skater.