7 Times Funny Lady Whoopi Goldberg’s Outfits Didn’t Do Her Justice

Whoopi attended the 65th Annual Academy Awards to support the film The Color Purple in which she starred as Celie. She made a bold fashion choice for the evening, opting for a lime green and purple ensemble. It was somewhere between a gown and a pantsuit. The top part had a bolero-style jacket but the bottoms had both pants and a skirt. Her shoes matched the pattern found on the outfit.

Whoopi had high hopes for her Oscars outfit. She was inspired by the great Lucille Ball's iconic character Lucy. "Lucy would always come out in these great ensembles," she mused to Page Six. "And I thought, 'I would like to wear that!' And green is not a color I would normally wear, let me try it!"

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Fashion critics were not too kind about this look and this greatly impacted the star. She opened up about it to Page Six Style in 2024. "It hurt my feelings, I’m not going to lie. It hurt my feelings," she told the outlet.

"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 mused.

Thankfully, Whoopi has learned over the years to have a pretty thick skin.

In 1995 Whoopi got her hand and foot print immortalized at the famous Mann's Chinese Theater in Hollywood. She wore a floral oversized dress for the occasion. It looked like something she just threw on quickly. She probably could have done better for such a special occasion.

This is another '90s fashion miss. In 1999, Whoopi attended Divine Design at the Pacific Design Center in West Hollywood, California. She donned a black suit jacket with a white shirt underneath. It was giving priest/prince vibes, which might not be exactly what she was going for.

It's fun to get awards and be recognized for your work. On June 6, 1997, Whoopi received the Toyota Comedy Award at Gracie Mansion in New York City. She chose to wear an oversized beige sweater dress and a big scarf. Perhaps it was cold, but we wish she would have found a way to stay warm and be a little more fashionable.

Over the years, Whoopi has appeared on many talk shows. She's even a host now herself on The View. This fashion crime took place on June 23, 1994, on The Tonight Show With Jay Leno. She wore a dress that looks like it came from Old Navy and she bought it in all the colors. She also took her purse out with her. Maybe the she thought the PA looked shady and didn't want to leave it backstage. Who knows?

In 2023, Whoopi worn a pair of shoes that caused quite a stir on The View. She donned ankle boots that featured decapitated Barbie heads in the heel. She was trying to celebrate the Barbie film, but some people didn't see it that way. You can't win them all.

In 2022, Whoopi shared a pair of high-heeled Crocs on Instagram. She apparently got them from the Broadway cast of the show POTUS. Perhaps they hate her. Just no.

Whoopi's experiences being on worst-dressed lists inspired her to start her own fashion line called DUBGEE in 2019. She wanted people to be able to dress comfortably while still looking cute. This line goes up to size 24 and is affordably priced.

She never wants anyone to feel bad about their clothing. "This is as serious to me as anything else I’ve done in my life," Whoopi explained to Business Fashion. "The first thing you should communicate is 'I like me.' I think the motto of the company is 'The last thing you should ever fret about is what’s in your closet.'"

"I never want to explain why I have something on," she continued. "Who’s to tell you it’s wrong? Nobody. If I’m happy, leave me alone about what I’ve got on. Maybe I was ahead of my time. Maybe now is the time."