There are a lot -- seriously, a lot -- of sartorial offenders for your consideration, but we've narrowed it down to five that truly take the prize.
1. Demi Moore, 1989
For some reason the bike shorts-lace bustier-grandma's drapes-sheer black hose look never caught on. For some reason.
2. Billy Bob Thornton, 1997
We get it, Billy Bob, you like ZZ Top. That doesn't mean you need to wear a baseball cap to the Oscars. The blue ribbon, in honor of Arkansas tornado victims, was a nice touch -- but it doesn't make up for that tie.
3. Kate Hudson, 2001
Perhaps the worst thing about this look is its historical inaccuracy. Nineteenth-century cowgirls didn't have perms, Kate!
4. Gwyneth Paltrow, 2002
If you ever wondered what Heidi would look like as a goth teenager, wonder no more.
5. Robert Downey Jr., 2010
How many times does it need to be said? Gentlemen, you have it easy when it comes to awards season: Find a nice tux. Put on the nice tux. Then wear shoes. These simple steps proved to be too much for Robert Downey Jr., who arrived on the red carpet in a bright blue bow tie and high-top sneakers.
More Oscars coverage from Surge Desk:
Oscars Acceptance Speech: The 7 Best of All Time [VIDEOS]
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