The Worst Oscars Black Fashion Trainwrecks Over the Years

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!

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!

2018: Maya Rudolph

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

1993: Whoopi Goldberg

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

2010: Zoe Saldana

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

2020: Billy Porter

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

2020: Blac Chyna

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.

2014: Pharrell Williams

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.

2021: Halle Berry

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.

2024: Cynthia Erivo

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

1997: Dennis Rodman

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.

2017: Terrence Howard

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

1971: Isaac Hayes

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

2007: Jennifer Hudson

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.

2005: Taraji P. Henson

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

2000: Tyra Banks

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