Whoopi Goldberg made a weak attempt at flaunting her new figure at the 2025 Oscars in a metallic Christian Siriano ball gown. With the exaggerated shoulders, voluminous skirt, and fabric as reflective as a road sign, the look certainly wasn’t Goldberg’s best, but we can’t say it’s the worst.

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OMG! miedo!! WHOOPI GOLDBERG en 1993 #Oscars #desdelosangeles #bestgownsever #mujerescestilo #deterror pic.twitter.com/cUPUdri2wl

— Sofi Zermoglio (@SofiZermoglio) February 27, 2014

In 1993, Goldberg stepped out onto the Oscars red carpet and turned heads with one of her most interesting looks ever. Straight out of a “Hocus Pocus” film, the TV personality donned a green jumpsuit with purple embellishments, an overlaying bolero jacket, and an open-front skirt that featured bolder shades of purple and green. To finish off the look, Goldberg accessorized with color-coordinated kitten heels and statement earrings. The look was met with scathing reviews, which transformed the way the “Sister Act” star approached red carpet looks.

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“It hurt my feelings, I’m not going to lie. It hurt my feelings,” she told Page Six in October 2023. “It kept me from dressing up for a very long time. You have to remember, in those days, they would say things and you’d think, ‘Do I really look that ridiculous?'” She went on to explain how Lucille Ball (star of “I Love Lucy”) was her inspiration behind the bold outfit, as Goldberg admired Ball’s outfits and wanted to try something similar out herself. As for whether she regretted the highly criticized look, she did not, and it’s safe to say old habits die hard after 2025’s awards show.

Whoopi Goldberg may not hold onto any resentment for her previous fashion risks, but she has revealed that styling hasn’t always been her strong suit. “If it fits and it’s comfortable, I put it on,” she disclosed to People in March 2025. “I wish I could tell you it’s deep like that, but it’s not.” It comes as no surprise that Goldberg takes a more lax approach to her looks, as she’s admitted that she rocks a pair of jeans when going to the gym.

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Despite her controversial outfit choice in 1993 being labeled as one of the Oscars’ worst-dressed moments over the years, Goldberg eventually shook off the criticism, and she also doubled down on defending her 2025 Oscars look. According to People, the gown was fresh from its runway debut and custom-made for the actor and TV host. “The dress was stunning,” she said. “He created a dress, and all I had to do was put it on and it fit. It was heaven.” Maybe the laid-back approach is the ideal style choice after all.