With the 2026 Oscars just days away 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 so 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 2026 Grammys, 2026 AAFCA Awards, and most recently the NAACP Image Awards and Actor 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 been more than a few 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 policeperson’s head.
2025: Yasmin Finney
The main reason this look is on this list is that we can’t see the dress for the trees long peacock feathers that are blocking our view. It’s a bit too distracting, which keeps it from being the show-stopper that it could have been.
2025: Anok Yai
For someone as insanely gorgeous as Anok Yai, this look didn’t give what it should have. (Which is really a shame because she could make a paper bag look like high fashion).
2025: Bresha Webb
While this color looks great on Bresha Webb, the proportions are just way off. It looks like it’s overpowering her and that’s sad because otherwise, the dress would’ve been a hit!
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, which makes this look a total bummer.
2024: Cynthia Erivo
Now, Cynthia, we know you were serving Elphaba-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 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 in the running for the Oscars best-dressed list with this look.
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