During awards season, celebs feel like princesses. Between December and March, designers send stars endless dress options, jewelers practically throw baubles their way, and A-list stylists clamor to be the ones to pull it all together for them. It can be overwhelming, dizzying — and ultimately, for some, the pressure results in a totally ass-backwards Oscar night look (in 1999, Celine Dion took this literally, showing up in a backwards tux). And then there’s the phenomenon we like to call Big Night Fail, where even the most stylish actresses look dazzling for every other awards show, but trip up for the Oscars (we’re looking at you, Kate Hudson in 2001).
The other issue? Sometimes, stars decide to buck the whole “elegant” moment and go for an avant garde outfit that misses the mark spectacularly, like biker shorts with a bustle, or…well, that swan thing. And Gwyneth, we love you (sometimes), but that gloomy, braless dress you wore in 2002 falls under this category.
Here, let’s look back at ten of the most confusing Oscar night dresses in history!