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The Worst Oscars Black Fashion Trainwrecks Over the Years

The Worst Oscars Black Fashion Trainwrecks Over the Years

Though the best looks are often cause for fanfare, not every celeb hits the mark. In fact, some miss it entirely. So let's take a look!

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Whoopi Goldberg during 65th Annual Academy Awards at the Shrine Auditorium in Los Angeles, California.
Whoopi Goldberg during 65th Annual Academy Awards at the Shrine Auditorium in Los Angeles, California.
Photo: Kevin Mazur/WireImage (Getty Images)

With the 2025 Oscars just days and awards season nearing its end, we’d be remiss not to share how excited we are about all the beautiful fashions we’ve seen thus far. And trust us, there are a lot!

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Since the Primetime Emmys kicked things off last September, we’ve been served some seriously stylish looks from some of our faves As the season went on, shows like the 2025 Grammys and NAACP Image Awards were also prime spots for some gorgeous looks.

But, just because we’ve gotten accustomed to seeing some glamorous looks—that doesn’t mean there haven’t been some misses along the way. Specifically, when it comes to the Oscars, there have more than its fair share of truly questionable looks that have graced the carpet. So, with that in mind, let’s take a look at some of the worst looks of all time in Oscars history. Whether they’re sporting too many ruffles or crazy colors—these looks are no doubt seared into every fashion policemen’s head.

So, keep reading and get into all the head-scratching style!

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2018: Maya Rudolph

2018: Maya Rudolph

Maya Rudolph arrives at the 90th Annual Academy Awards at Hollywood & Highland Center on March 4, 2018 in Hollywood, California.
Maya Rudolph arrives at the 90th Annual Academy Awards at Hollywood & Highland Center on March 4, 2018 in Hollywood, California.
Photo: Steve Granitz/WireImage (Getty Images)

While monochrome is hardly ever a bad idea, Maya you’re making us hot just by looking at you.

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1993: Whoopi Goldberg

1993: Whoopi Goldberg

Whoopi Goldberg during 65th Annual Academy Awards at the Shrine Auditorium in Los Angeles, California.
Whoopi Goldberg during 65th Annual Academy Awards at the Shrine Auditorium in Los Angeles, California.
Photo: Kevin Mazur/WireImage (Getty Images)

Whoopi: you’re an icon and a legend. But this was A MISS OF ALL MISSES.

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2010: Zoe Saldana

2010: Zoe Saldana

 Zoe Saldana arrives at the 82nd Annual Academy Awards at the Kodak Theatre on March 7, 2010 in Hollywood, California.
Zoe Saldana arrives at the 82nd Annual Academy Awards at the Kodak Theatre on March 7, 2010 in Hollywood, California.
Photo: Kevin Mazur/WireImage (Getty Images)

The purple ombre frills might have been okay, but the top part of the dress just throws it off.

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2020: Billy Porter

2020: Billy Porter

Billy Porter on the red carpet at the 92nd Academy Awards held at the Dolby Theatre in Hollywood, Los Angeles, USA.
Billy Porter on the red carpet at the 92nd Academy Awards held at the Dolby Theatre in Hollywood, Los Angeles, USA.
Photo: Jennifer Graylock/PA Images (Getty Images)

Billy Porter has never shied away from making a statement on red carpets but this one didn’t land the way it needed to.

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2020: Blac Chyna

2020: Blac Chyna

 Blac Chyna arrives at the 92nd Annual Academy Awards at Hollywood and Highland on February 09, 2020 in Hollywood, California.
Blac Chyna arrives at the 92nd Annual Academy Awards at Hollywood and Highland on February 09, 2020 in Hollywood, California.
Photo: Steve Granitz/WireImage (Getty Images)

We’re all for a nice thigh split and a plunging neckline, but there has to be balance somewhere. And that’s the only reason why this is missing the mark.

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2014: Pharrell Williams

2014: Pharrell Williams

Pharrell Williams (L) and Helen Lasichanh arrive at the 86th Annual Academy Awards at Hollywood & Highland Center on March 2, 2014 in Los Angeles, California.
Pharrell Williams (L) and Helen Lasichanh arrive at the 86th Annual Academy Awards at Hollywood & Highland Center on March 2, 2014 in Los Angeles, California.
Photo: Dan MacMedan/WireImage (Getty Images)

We know Pharrell has never been afraid to push the boundaries when it comes fashion. But shorts? At the Oscars? We don’t think so.

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2021: Halle Berry

2021: Halle Berry

Halle Berry attends the 93rd Annual Academy Awards at Union Station on April 25, 2021 in Los Angeles, California.
Halle Berry attends the 93rd Annual Academy Awards at Union Station on April 25, 2021 in Los Angeles, California.
Photo: Chris Pizzello-Pool (Getty Images)

Halle, we might have let this dress slide if it wasn’t for the hair. The hair is what makes this look a total bummer.

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2024: Cynthia Erivo

2024: Cynthia Erivo

Cynthia Erivo attends the 96th Annual Academy Awards on March 10, 2024 in Hollywood, California.
Cynthia Erivo attends the 96th Annual Academy Awards on March 10, 2024 in Hollywood, California.
Photo: Mike Coppola (Getty Images)

Now Cynthia, we know you were serving Elpha-tease, but it didn’t defy as much gravity as we wish it would’ve.

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1997: Dennis Rodman

1997: Dennis Rodman

Dennis Rodman arrives for the 69th Academy Awards ceremony at the Shrine Auditorium in Los Angeles, 24 March.
Dennis Rodman arrives for the 69th Academy Awards ceremony at the Shrine Auditorium in Los Angeles, 24 March.
Photo: VINCE BUCCI/AFP (Getty Images)

Dennis Rodman showing up as the Mad Hatter at the Oscars is a bit more off-putting than we realized. And that’s saying something.

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2017: Terrence Howard

2017: Terrence Howard

Terrence Howard attends the 89th Annual Academy Awards at Hollywood & Highland Center on February 26, 2017 in Hollywood, California.
Terrence Howard attends the 89th Annual Academy Awards at Hollywood & Highland Center on February 26, 2017 in Hollywood, California.
Photo: Kevin Mazur (Getty Images)

Bathrobes will never a viable option for a suit jacket....sorry, Terrence.

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1971: Isaac Hayes

1971: Isaac Hayes

Image for article titled The Worst Oscars Black Fashion Trainwrecks Over the Years
Photo: Bettman (Getty Images)

Isaac Hayes may be super talented in the music space, but this blue furry suit isn’t hitting all the right notes.

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2007: Jennifer Hudson

2007: Jennifer Hudson

 Jennifer Hudson attends the 79th Annual Academy Awards held at the Kodak Theatre on February 25, 2007 in Hollywood, California.
Jennifer Hudson attends the 79th Annual Academy Awards held at the Kodak Theatre on February 25, 2007 in Hollywood, California.
Photo: Frazer Harrison (Getty Images)

The half jacket is what really kept this look from being a truly stylish moment, which sucks because Jennifer went home with the gold that night.

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2005: Taraji P. Henson

2005: Taraji P. Henson

Taraji Henson during The 77th Annual Academy Awards - Red Carpet at Kodak Theatre in Hollywood, California, United States.
Taraji Henson during The 77th Annual Academy Awards - Red Carpet at Kodak Theatre in Hollywood, California, United States.
Photo: Kevin Mazur (Getty Images)

Taraji, we love you and we see what you were trying to do, but this was a miss.

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2000: Tyra Banks

2000: Tyra Banks

Image for article titled The Worst Oscars Black Fashion Trainwrecks Over the Years
Photo: Steve Granitz (Getty Images)

Sorry, Tyra. But you won’t be making it to the top with this lilac-colored dress.

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