OSCARS

Taking a Look Back at the Worst Oscar Dresses of All Time

by Emily Krauser 7:00 PM PST, February 23, 2017
Photo: Getty Images

When a dress fails at the Oscars, it's usually not just a mere misstep, but a major miscalculation. 

Even the most fashionable celeb can fall victim to a faux pas on Hollywood's biggest night. Often, it's because they were just trying to stand out, but the Academy Awards red carpet is a tough place to pull off a big risk.

PHOTOS: Worst Dressed Stars at the 2016 Oscars

Take, for instance, Heidi Klum, who joined the all-time worst dressed list last year, when she hit the red carpet in a lilac Marchesa confection. While the hue was stunning, there was too much tulle, competing oversized flowers and, sadly, not enough sleeves.

Photo: Getty Images

Plenty of fans had a field day trying to turn the sartorial slip-up into Easter puns, but the frilly frock pales in comparison to some of the most memorable looks of all time -- for all the wrong reasons.

There was the strapless Dior dress that Charlize Theron donned in 2010, which now seems like it set the stage for Klum:

Photo: Getty Images

Oscars Flashback: Emma Stone and Anne Hathaway Lead the Pack in Stunning Yellow and Gold Gowns

And the white Christian Dior suit that Celine Dion inexplicably wore backwards in 1999:

Photo: Getty Images

Both of those, however, pale in comparison to Gwyneth Paltrow's goth turn in 2002:

Photo: Getty Images

Or Bjork's now-infamous swan dress from 2001:

Photo: Getty Images

From Gwen Stefani to Diane Kruger: Let's Talk About Those Nearly Nude Dresses at the 2016 Oscars

Which other looks have made us scratch our heads over the years? Click through the gallery below to find out!

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