Taking fashion risks at the Met Gala can definitely pay off, but not every risk ends up with a winning look. Trying too hard or not trying at all can lead to some pretty big fashion disasters at the annual Metropolitan Museum of Art’s Costume Institute fundraising gala.

See some of the worst Met Gala looks of all time, that failed to impress fashion critics and turned out to be a major misfire for the designers who created them.

Victoria Beckham in 2003

Attending the Met Gala with Domenico Dolce and Stefano Gabbana, Victoria Beckham was far from her fashion high point in 2003. The theme of the ball was “Goddess: The Classical Mode”, and her lingerie inspired dress was anything but fitting. 

Victoria Beckham 2003 Met Gala

Luckily, Victoria made less and less fashion mistakes in the following years, and her career as a fashion designer is based on a very different aesthetic.

Shailene Woodley in 2014

Shailene Woodley 2014 Met Gala

At the “Charles James: Beyond Fashion” themed Met Ball, Shailene Woodley wore Rodarte and failed to make it her own. While the “Divergent” star has a unique fashion sensibility and she can pull off clothes most celebrities couldn’t, the busy effect of all the prints and colors ended up creating one of the worst Met Gala looks of all time.

Mischa Barton in 2008

Mischa Barton 2008 Met Gala

For “Superheroes: Fashion and Fantasy”, Mischa Barton wanted to go in a very different direction. However, her Missoni gown fails even as something that a damsel in distress would wear. It’s not just thematically dissonant to the event, it’s just ugly, from the ruffled sleeves to the blah color of the skirt.

Alicia Keys in 2003

Alicia Keys 2003 Met Gala

Definitely one of the worst Met Gala looks of all time, Alicia Key’s white tuxedo failed as spectacularly as the dress worn by Victoria Beckham the same year. Even when completely removing the “Goddess: The Classical Mode” theme, the white tuxedo was just too simple, and the sparkly vest, along with her earrings amounted to a really inspired look.

Florence Welch in 2012

Florence Welch 2012 Met Gala

For the “Schiaparelli and Prada: Impossible Conversations” themed Met Gala, Florence Welch tried to stick to her chic hippie vibe, but failed, even in Alexander McQueen. The Fall 2012 collection gown looked much better on the runway with futuristic headgear. At the Met Ball, the singer showed it off by spinning for the paparazzi, and ended up more with a more car wash vibe.

Kirsten Dunst in 2007

Kirsten Dunst 2007 Met Gala

Proof that you aren’t guaranteed a style win even if you opt for vintage, Kirsten Dunst’s YSL dress from the 2007 event is also one of the worst Met Gala looks of all time. Even though her look was fitting for the “Poiret: King of Fashion” theme, the flapper headgear didn’t really work with the dress, and the result was less than stellar.

Frieda Pinto in 2011

Frieda Pinto 2011 Met Gala

For the “Alexander McQueen: Savage Beauty” Met Gala, many celebrities opted for the obvious, wore McQueen and got on the best dressed list. Frieda Pinto tried something different in Chanel, but her white gown with a black necktie detail failed to impress on the red carpet, or even match the original haute couture design.

Hilary Swank in 2004

Hilary Swank 2004 Met Gala

Looking like you’re wearing something off the rack at the Met Ball is the equivalent of showing up in flip-flops at the Academy Awards. Hilary Swank chose a completely uninspired Calvin Klein gown, even though the theme of the event that year was the inspiring “Dangerous Liaisons: Fashion and Furniture in the 18th Century”, and ended up with one of the worst Met Gala looks of all time.

Chrissy Teigen in 2011

Chrissy Teigen 2011 Met Gala

“Project Runway” contestant and “Mad Fashion” star Chris March designed Chrissy Teigen’s gown for the “Alexander McQueen: Savage Beauty” Met Gala, and he was the first to admit how disappointing it turned out. March’s original concept featured a leather neckpiece, but it’s unlikely that it would have made a difference in the end.

Kim Kardashian in 2013

Kim Kardashian 2013 Met Gala

Definitely one of the worst Met Gala looks of all time, Kim Kardashian’s custom Givenchy gown wasn’t just ugly, it was way off the mark for the “Punk: Chaos to Couture” theme. However, any publicity is good publicity for Kim, so she was probably quite happy that her dress turned into a meme.