In 1986, Cher was a presenter at the awards. And she showed up… In this. She was dressed by costume designer Bob Mackie, who has scored several wins (good ones) on the Oscars carpet for other outré designs. This feathered headpiece, cutout panelled crop and sequinned pants was a head-turner. And a head-scratcher.

The infamous swan dress Icelandic singer Björk wore in 2001 was designed by Marjan Pejoski. The outfit was accessorised with ostrich eggs, which the performer “laid” on the red carpet as she passed through. The event could be called a precurser to Lady Gaga’s various outfits, and has been been spoofed in movies like White Chicks. Heck, it inspired a Valentino haute couture creation in 2014.

The Oscars Vanity Fair party is also where it’s at for fashion, and actress Charlize Theron was unforgettable in this tangerine ruched, backless dress at the 2000 Oscars. Despite looking fierce AF, Charlize said in an 2004 interview to the Baltimore Sun that the outfit actually led to a setback in her career. How? She looked so hot in it that directors subsequently didn’t think she could pull off serious roles.

In 1995, Australian costume designer Lizzie Gardiner won big for her work in comedy-drama The Adventures of Priscilla, Queen of the Desert, where she snagged best costume design. The American Express dress — made with 254 genuine but expired credit cards — was a sign of her creative energy. It may have been called one of the worst Oscars dresses of all time, but it reportedly scored her an ad campaign with the financial services corporation.

Perhaps this outfit could be stylish in an alternate Aladdin universe. But the outfit worn by EGOT (Emmy, Grammy, Oscar and Tony) winner Whoopi Goldberg when she was a presenter at the 1993 Oscars, is not, erm, stylish. The weird combination of lime and purple in the paisley pantsuit, paired with dangly studs and matching pumps, was all wrong.

The Batman actress and Bond Girl (1983’s Never Say Never Again) stunned the crowd in the 1990 Oscars gown which she designed herself. Sadly, the ensemble featured too many competing details, from the white satin ballgown silhouette, to the one-gloved arm and popped collar.

Jennifer Lawrence was beautiful in this Raf Simons Dior Couture gown. But she tripped on the skirt as she was heading to the stage to collect her award for Best Actress (Silver Linings Playbook). According to Jen, her stylist told her to “kick and walk” , but her mind was on cake, which led to her fall.

1969 was the first time that the Awards were broadcasted live worldwide. It was also the first time in three decades that there was a tie for the title of Best Actress (the award went to Barbra Streisand and Katherine Hepburn). But Babs also made history that night with a sheer sequinned pantsuit by Arnold Scaasi. The Funny Girl actress reportedly did not know that the bright lights would cause her outfit to become see-through.

Two words — Leg bomb. That pose made the 2012 Oscars, and led to so many memes and spoofs. The slit-to-there Atelier Versace on Angie (now in a divorce war with Brad Pitt) also led to the Twitter account, Angie’s Right Leg, which had 38,000 followers at one point.

South Park creators Matt Stone and Trey Parker (left and right in green and pink) were Comedy Central in their Oscars outfits in the year 2000. These were spoofs on Jennifer Lopez’s famous green V-neck Versace Grammy Awards dress, and Gwyneth Paltrow’s pink Ralph Lauren seen at the 1999 Academy Awards. We likey.

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Text: Ho Guo Xiong