Unisex Black Dress
Well, there have been plenty of stars to grace the red carpet at the Met Gala throughout the years in black lace/sheer dresses – though, for the most part, they’ve been women.
Getty Images Photo by Randy Brooke/WireImage
But designer Marc Jacobs decides to mix things up at 2012’s NY event by showing up in this long, see-through shirt dress over a pair of white boxers. And might we add that he may have won the prize for the most controversial male outfit for that year? Just saying. But, hey, it looks a hell of a lot more comfortable than the majority of other looks on our list, that’s for sure!
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Back to the Future
You know, Woodley’s look also seems like it may have fit in better at the 2016 Gala, with its Star Trek-like feel. Katy Perry arrived in this fitted, black, and gold Prada gown. The dress is pretty lovely, but it’s the hair and makeup that throw the look off.
Getty Images Photo by Jamie McCarthy/FilmMagic
With the combination of a beehive and black lipstick, it’s hard to want to nominate her for any best-dressed awards. In fact, the getup landed her on several worst-of lists. Perry is no stranger to taking risks when it comes to over-the-top fashion, and this may be one of those occasions that the risk didn’t work out in her favor. Oops!