Celine Dion (1999) 

If Celine Dion could dress as well as she can sing, we would all celebrate. Unfortunately, this was not the case with the outfit that the singer wore to the 1999 Oscars. The backwards jacket, loose pants, funky fedora and dated sunglasses all added up to a major fashion crime.

Who could forget the time Lara Flynn Boyle channeled her inner ballerina and wore a full-on tutu and matching ribbon-tied shoes? The ensemble, which looked like a sad attempt at a Halloween costume, was nothing short of ridiculous. The actress would have been better off if she just kept this dress locked in her closet. 

Geena Davis, we will never find out what was going through your mind when you chose this mess of a dress. The gloves, the shoes, and (most importantly), the ruffles are simply ghastly. Sure, the 90's were not the most fashionable years, but that does not serve as a valid excuse. At least Geena can find solace in the fact that the only way from rock bottom is up.

This bizarre outfit looks like a Disney princess dress gone horribly wrong. The shiny white fabric, overly-puffy skirt and odd half-jacket made this creation fit for anything but royalty. Her frazzled hair, tacky red lipstick and too-tight satin glove made the outfit all the more painful to see. 

Bjork’s 2001 Oscars outfit definitely grabbed people’s attention, but for all of the wrong reasons. The Icelandic singer walked the red carpet looking like a flamenco dancer gone wrong. Hopefully she learned that it is always better to leave the bird at home. 

It is not hard to see why this monster of a dress made it onto our list. Everything from the spiked headpiece to the hideous bralet and Harry Potter cape is wrong. It is no wonder why this Bob Mackie number has become one of the most infamous Oscar dresses of all time.

Last (but certainly not least) in our hall of fashion shame is Faye Dunaway. To say that her black dress at the 2007 Oscars was a monstrosity would be a gross understatement. We will never know why she would purchase such an outfit, but hopefully she has developed some fashion sense since.