The 10 biggest Oscars fashion fails of all time, from Whoopi Goldberg’s Disney villain look and John Travolta’s jeans, to Jenny McCarthy’s backwards Valentino and that American Express gown

Mar 30 , 2022

What are the worst fashion fails in Oscars history? Photos: Wire, Getty

Lizzy Gardiner’s American Express dress turned heads and is now iconic, while Dennis Rodman attended the 1997 Oscars in an outfit that resembled Willie Wonka’s

Björk’s swan dress laid ‘eggs’ on the red carpet, Uma Thurman intentionally went for ‘worst dressed’ and George Clooney saved his date when her dress ripped

Award season is back in full swing with celebrities strutting their red carpet looks – for better or worse. This year’s Oscars has seen some dazzling jewels and sweeping fashion ensembles, and let’s not forget one of the most shocking moments in Academy Awards history. But what about the awkward fashion moments of years past?

We take a look back at the 10 biggest red carpet fashion fails in Oscars history.

1. In 2001, Björk wore a white swan dress, complete with an orange and black beak

Actress and singer Björk waves to the public wearing a swan-themed dress at the 73rd Annual Academy Awards at the Shrine Auditorium in Los Angeles, in 2001. Photo: AFP

In 2001, Icelandic singer Björk, who was nominated in the best original song category, hit the red carpet wearing a crystal-embellished white tulle dress featuring the neck of a fake swan draped around her own neck.

According to BBC, she went a step further by accessorising with massive eggs, which she “laid” on the red carpet.

Icelandic singer Björk in 2001 drops a huge egg on the Oscars red carpet in 2001. Photo: Reuters

What is now considered one of the most iconic Oscar dresses ever worn wasn’t at all well-received on the night. Fashion critics, like the late Joan Rivers, did not take kindly to the look but it has since become a revered style moment. The Met’s exhibition “Gala Camp: Notes on Fashion” even featured it.

2. In 1986, Oprah Winfrey struggled to zip up her dress

Oprah Winfrey and Akosua Busia at the 58th Annual Academy Awards in Los Angeles, in 1986. Photo: Getty

Oprah Winfrey’s first time at the Oscars in 1986 was one she’d rather forget. During an appearance on Jimmy Kimmel Live in 2012, she said she’d hired Dolly Parton’s dressmaker to make some last-minute adjustments to her dress, Access Online reported. Her mistake was not trying it on until 30 minutes before needing to leave for the event.