Whoopi Goldberg Outfits That Missed The Mark

After decades in the entertainment industry, actor, comedian, and TV host Whoopi Goldberg is Hollywood royalty. She was even the first Black woman to complete an EGOT run by earning an Emmy, a Grammy, an Oscar, and a Tony. However, her time in the public eye hasn't equated to the strongest sense of style — rather, Goldberg describes herself as the opposite of a choosy clothes horse. "I wish I could tell you it's deep like that, but it's not," Goldberg told People in 2025. "If it fits and it's comfortable, I put it on." 

That said, Goldberg is an outspoken advocate for authentic personal style, regardless of appearance, age, and trendiness. "I never want to explain why I have something on. ... Who's to tell you it's wrong? Nobody. If I'm happy, leave me alone," she explained to Business of Fashion in 2019. Frustrated by constrained fashion standards, Goldberg even launched her own quirky and size-inclusive clothing line, Dubgee, that year — and has joked that its motto is "The last thing you should ever fret about is what's in your closet."

Unlike many other would-be celebrity designers, Goldberg doesn't claim any sartorial insight. "I've never been known as one who had anything really loving to do with fashion," Goldberg told Interview Magazine in early 2025. "I've developed my own thing." Her "thing" theoretically includes recognizing when a garment isn't the right fit, literally or stylistically. "At some point, you have to draw the line and say ... 'I know that when I put it on, it's wrong.'" However, this sixth sense hasn't always saved the "The View" host from stepping out in less-than-ideal ensembles. Perhaps betraying her indifference to fashion trends, some of Goldberg's outfits have missed the mark, from high-drama red-carpet flops to her years of nothing-burger street clothes.

Attending the Oscars in 1993, Whoopi Goldberg took a big swing by strutting her stuff in a royal-purple outfit that put an extra-jazzy spin on red-carpet couture: The seemingly demure skirt opened like a trenchcoat to reveal busy brocade pants and eye-searingly green lining. While the color palette might seem strikingly similar to The Joker of "Batman" fame, Goldberg says the whimsical styling was actually inspired by "I Love Lucy." Unfortunately, fashion critics didn't respond well to the gown's surprisingly neon under-layer. As Goldberg told Page Six in 2023, "everyone hated" the outfit, and she landed on many worst-dressed lists, including a spot among the worst-dressed celebs in Oscars history. "It hurt my feelings, I'm not going to lie," said Goldberg, tragically adding, "It kept me from dressing up for a very long time." 

After getting stung at the Oscars, it seems that Whoopi Goldberg really did avoid dressing up — the following years saw the "Ghost" actor lean hard in the other direction, eschewing formal fashions. For instance, Goldberg immortalized her foot and handprints in cement outside Hollywood's famous Mann's Chinese Theater in 1995, but she dressed down for the career-defining ceremony, choosing a white, floral dress so breezy and amorphous that it gave nightgown vibes. Not only is shapelessness one of the dress mistakes that can make you look older, but it also totally undermines any refinement in a look. And Goldberg's styling didn't do much to elevate this particular frock; the choice to complete her already-pedestrian outfit with chunky tube socks and clogs felt too casual for the high-profile event.

By the mid-'90s, Whoopi Goldberg had all but disappeared into the oversized clothing that would define her style for the remainder of the decade (and into the 2000s). While some of these outfits exuded a certain cool factor, the repetitive aesthetic and total lack of tailoring didn't befit a star of Goldberg's caliber. For example, Goldberg rocked up to the 1996 MTV Movie Awards in a baggy leather jacket and an equally cavernous white button-up, both worn over forgettable black trousers and shoes. While we appreciate Goldberg's stab at androgyny, the final ensemble failed to captivate — as did her many nearly identical looks during this period. Looking back, it's a shame that Goldberg spent so many years afraid to revisit statement pieces on the red carpet.

The 2000s saw Whoopi Goldberg continue her endless rotation of irreverent and oversized fashions, even when promoting her own work. At an event called An Evening with the Hosts of "The View" in 2008, Goldberg stood out from her dressier cohosts by throwing on jeans, an untucked T-shirt, and a grungy zip-up jacket that could have come straight from Hot Topic. It was like an outfit a teenage boy might throw on for school, giving the impression that Goldberg put no thought or effort into her look. Notably, it was around this time that Goldberg started taking baby steps back into the world of couture fashion. Tapped to host the Tony Awards that year, Goldberg apparently "called and begged" designer Christian Siriano to dress her. As she later admitted on "The View," this was out of self-aware desperation. "I saw what he did, and I was like, 'Please help me!'"

Whoopi Goldberg's return to high fashion hasn't always been a smooth one. When the celebrated "The Color Purple" actor started taking risks again, she also put herself out there to make new style missteps. For instance, Goldberg's eccentric look at The Face of Tisch Gala in 2010 was serving oblivious art teacher. The fuzzy coat and gauzy scarf combo was aggressively bohemian, while the beret-coded statement hat, complete with its upside-down snail embellishment, was simply puzzling. Goldberg went from doing too little to doing too much, and though this look was probably a conversation starter, we can't call it a success. At least it felt like a breath of fresh air after years of nondescript basics.

At first glance, Whoopi Goldberg's glamorous outing at the 2025 Oscars might seem out of place on this list, but her bespoke Christian Siriano gown divided opinions. Some folks adored the dress, which shone like liquid metal. "It's mesmerizing," wrote one user on Reddit. However, others named Goldberg one of the worst-dressed celebs at the 2025 Oscars, arguing that the gown's structural neckline and voluminous skirts swallowed her up. As for the "Sister Act" star, Goldberg loved that the stunning look was in keeping with her unfussy fashion sensibility, telling People that Siriano "created a dress and all I had to do was put it on and it fit. It was heaven."

Ultimately, we're just glad that Goldberg has bounced back from harsh critiques and continued pushing the boundaries of style. Even if her looks don't always land, they're now a lot more interesting to watch. As Goldberg herself told Business of Fashion, "For me, the idea has always been to be comfortable. ... Maybe I was ahead of my time. Maybe now is the time."