The Most Cringe-Worthy Outfits From The 2025 Oscars

The 97th annual Academy Awards ceremony is finally upon us, and while many people around the world are on the edge of their seats, waiting for the winners to be revealed, let’s first take a look at those who have arrived — and what outfits they’re wearing.

A celebrity’s fit is arguably one of the most important aspects of highly publicized events such as the Oscars, and for good reason. Pictures are constantly being taken, even during seemingly unsuspecting moments. 

But from X to Y, here are a few stars that didn’t quite hit the mark for us. Feel free to disagree — after all, conversation surrounding fashion is a part of the experience.

Fashionably challenged look at the Oscars 2025; woman in a mirrored strapless gown on the red carpet.

It seems as if the celebrities really want to be seen in the crowd tonight!

Halle Berry’s outfit, similar to Yvonne Orji, looked a lot like cracked glass. If the patterns were consistent with one another or the top wasn’t so clearly disconnected, maybe it would’ve worked. 

However, adding minimal jewelry and keeping a simple hair look was definitely the right move.

Savion Washington / Getty Report

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    Fashionably challenged look at Oscars 2025, featuring a black and white floral gown on the red carpet.

    The Treat Me Like Fire star had a good thing going for her dress until it got to the very bottom. In fact, the last couple of inches of her outfit look strikingly similar to a few thick-heeled platform boots we’ve seen recently.

    Mike Coppola / Getty Report

    Fashionably challenged look at Oscars 2025, featuring a unique silver shoulder design on a sleek gown.

    Ava DuVernay’s outfit isn’t a bad look at all, but the shoulders are a little too distracting compared to the rest of her outfit.

    If it were less “in your face,” and fell to the side instead of standing stiffly, perhaps the elegant vibe of the gown may have worked better.

    Monica Schipper / Getty Report

    Fashionably challenged red carpet looks at Oscars 2025, featuring a unique teal gown and beige suit ensemble.

    It’s certainly… an interesting combination.

    Shekoni’s dress gives major Princess Jasmine vibes, but the darker blue accessory wrapped around her body doesn’t look to be the most comfortable — and the hair, as well.

    Grimonprez’s outfit, on the other hand, just didn’t have the right colors to make it work. The beige matching set and noticeable orange shirt underneath don’t compliment each other well.

    Mike Coppola / Getty Report

    Damned_Cat

    3 weeks ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    To me it looks like she forgot to bring a jacket and just grabbed the sunshade from the car window to use as a wrap.

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    Person in an extravagant green gown at the Oscars, showcasing a fashionably challenged look.

    It’s all in the shoulders!

    Laura Blount’s dress actually had so much good going on — from its beautiful emerald green to the charms embedded in the fabric. But the shoulders, particularly the one on her right, look as if it’s quite literally weighing down the entire look.

    Mike Coppola / Getty Report

    PunchinelloTX

    Premium

    3 weeks ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I think this gown escaped the set of Dynasty circa 1984 as it crawled away from Joan Collins.

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    Fashionably challenged look at Oscars 2025 with unique hair design and black gown on red carpet.

    Yasmin Finney looks amazing. There’s no doubt about that. The color works so well, and her gloves and feathers add the perfect touch to it all.

    But imagine sitting next to her? If she moves, you’re getting a free tickle. And no matter what, if you’re behind her, your view of whatever is happening on-stage won’t exactly be ideal.

    Arturo Holmes / Getty Report

    Woman in a sheer gown on the Oscars red carpet, showcasing a fashionably challenged look.

    It’s not the dress… it’s the way it looks as if the outfit is slowly falling down.

    In general, the gown also doesn’t have much volume. The color is great, and so are the small beads decorated in its material, but it sags a little lifelessly against Zegler’s body.

    Kevin Mazur / Getty Report

    Fashionably challenged look at the Oscars 2025, featuring a person in a shimmering silver gown on the red carpet.

    Emma Stone is one of Hollywood’s most popular actresses, but her dress certainly did not give off that impression. 

    In an event as big as the Oscars, one would expect celebrities to go all out. But Stone’s gown seems to have a shy personality. Pair that up with her slicked-back bun, and it definitely doesn’t exude confidence.

    Gilbert Flores / Getty Report

    Person in a light blue gown with cutouts at the Oscars 2025, showcasing a fashionably challenged look.

    Don’t get us wrong, Amelia Dimoldenberg is stunning in whatever she wears. But in our opinion, her other red carpet looks have been better. The baby blue works well, but there seems to be a bit too much design happening on her upper body.

    A few accessories on her arms and neck would’ve been a nice touch, as well.

    Mike Coppola / Getty Report

    Stylish man in red jacket with black trim at the Oscars 2025, holding sunglasses, exemplifying fashionably challenged look.

    To be clear, there’s nothing wrong with Colman Domingo’s outfit. The red goes well with his look, and the sunglasses in his hand only add to its charm.

    But given the stunning gowns and suits of so many other celebrities, it falls a little short simply because it doesn’t stand out.

    Kevin Mazur / Getty Report

    Jaya

    3 weeks ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    How does this not stand out? Have you seen how boring most of the other men dress? I think this is great, very groovy

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    Person wearing a fringed vest with floral patterns and a black outfit at the Oscars. Fashionably challenged looks.

    The patterns and the style of this filmmaker’s outfit are certainly unique, but the colors of his vest seem to clash a little with the rest of what he’s wearing.

    The red and green, of course, are perfectly fine as they resemble roses. But it’s the rusty yellow that clashes a little too much for our tastes.

    Mike Coppola / Getty Report

    Woman in a sheer black gown on the Oscars red carpet, showcasing a fashionably challenged look.

    It kind of looks like Josephine Reitman is ready for a funeral, rather than the Oscars.

    While that is mostly a joke, it seems as if the actress could’ve benefitted from a brighter color dress rather than the black she showed up with. Perhaps a baby blue or pink? After all, her stunning hair and jewelry are already dark shades.

    Monica Schipper / Getty Report

    Person in a bold blue embroidered blazer and white pants on the Oscars 2025 red carpet.

    There’s a lot going right for Emmanuel Janvier here. The colors are great, and the designs stand out perfectly. But the shape of his top is throwing us off a little. Maybe it’s hugging a little too close to his pants? Or it’s a little too low-cut?

    Savion Washington / Getty Report

    PunchinelloTX

    Premium

    3 weeks ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I like it for a summer wedding or a fun museum gala. Not for the Oscars. Wear a damn shirt.

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    A person in a gold metallic outfit on the Oscars 2025 red carpet, showcasing one of the fashionably challenged looks.

    We wouldn’t be surprised if Bretman Rock himself told us he had come straight from a movie set where he was playing a Greek warrior.

    Award shows do love bringing on the ‘extra,’ but the design of the influencer’s outfit seems a little off. If it was a one-piece instead of being detached from one another, it could’ve gone a completely different way.

    Arturo Holmes / Getty Report

    Fashionably challenged look at Oscars 2025, featuring a mirrored dress on the red carpet.

    Yvonne Orji’s Oscars 2025 look is the visual definition of a bit too much bling. Though the actress and comedian decided not to wear much accessories, her gown looks as if it’s a literal cracked mirror — reflecting light in excessive amounts.

    Mike Coppola / Getty Report

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    Person in a unique white suit with a checkered sash at Oscars 2025, showcasing fashionably challenged looks.

    It looks like Edvin Ryding loves his light-colored outfits, as his previous red carpet looks see him wearing similar hues of white.

    Maybe it’s the sash-like accessory on his left shoulder. Maybe it’s the stiff pose. But it’s giving the King’s Guard.

    Chelsea Guglielmino / Getty Report

    Person in a shiny, unconventional gown at the Oscars 2025, reflecting one of the fashionably challenged looks.

    If the dress was a little smaller and the shine wasn’t as spotlight-stealing, then perhaps this gown could’ve worked for Whoopi Goldberg.

    Instead, it just swallows her. With an already large, fanning skirt, it would’ve made much more sense for her top to fit closely with her upper body.

    Monica Schipper / Getty Report

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    A person in a black suit with metallic leaf design poses on the red carpet at the Oscars, showcasing a fashionably challenged look.

    There’s just not a lot going for Ornela March’s outfit. Besides the design that snakes across her left shoulder, it’s just an expanse of black.

    A pop of color or another major accessory would’ve gone a long way!

    Monica Schipper / Getty Report

    Jaya

    3 weeks ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Very pretty. Both a statement piece AND nicely understated. And don’t complain about it only being a boring black suit if 99% of the men on the red carpet wear only a boring black suit WITHOUT an interesting detail like the feather.

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    A couple on the Oscars 2025 red carpet, with fashionably challenged outfits in floral dress and classic tuxedo.

    Whoever sits next to Nicole Avant has got to be sneezing all night because there are simply too many flowers everywhere.

    While the design is certainly nice, we think the political activist could’ve made the look even better if the sleeves were a transparent black instead of being dotted with additional designs. Because, as it stands, the dress and its shape are quite flattering.

    Monica Schipper / Getty Report

    Person in pink off-shoulder gown on red carpet at the Oscars, showcasing one of the fashionably challenged looks of 2025.

    Rita Wilson looks as if she’s heading to a summer party instead of a star-studded event such as the Oscars. It looks nice — but it’s a little too casual, and compared to the other celebrities, it definitely falls short.

    Chelsea Guglielmino / Getty Report

    Tyranamar Seuss

    3 weeks ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I saw that dress in K-mart when I was 10 and I refused to wear it. I got the white sundress with the spaghetti straps and the little hearts.

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    Fashionably challenged look at Oscars 2025, featuring a tiered black dress with ruffled sleeves on the red carpet.

    There’s too much happening.

    From the layers of the dress, to the excessive ruffles, to the way it all flows down to the ground… it’s an attack on the eyes. Who knows? Maybe some other colors would’ve added a bit more to the look.

    Mike Coppola / Getty Report

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    A person in a brown ensemble posing on the red carpet at the Oscars 2025, showcasing a fashionably challenged look.

    Guneet Monga is incapable of looking anything other than beautiful — but her outfit kind of makes it look as if she’s stuck in the middle of a log.

    Maybe it’s the stiff figure and shape around her shoulders or the length of the material, but it certainly looks a little claustrophobic.

    Mike Coppola / Getty Report

    Person on Oscars red carpet in a bold black outfit with pink hair, showcasing a fashionably challenged look from 2025.

    Similar to Whoopi Goldberg, the outfit is just too big — particularly the giant ruffles around her shoulders. The train would’ve worked, as well as the rest of her all-black fit. 

    As it stands now, however, people can’t even catch a glimpse of her face without getting a whole lot of ruffle on the inside.

    JC Olivera / Getty Report

    Individual in a black cape dress on the Oscars 2025 red carpet, embodying a fashionably challenged look.

    The concept was there. The shape had potential, and her earrings are gorgeous. But it’s the all-black of the outfit that is throwing us off — not exactly a look, in our opinion, that screams Oscars red carpet.

    Mike Coppola / Getty Report

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    Fashionably challenged look featuring a see-through black dress on the Oscars 2025 red carpet.

    The dress honestly would’ve been considered a success if it weren’t for the random little flares by her waist and legs. 

    The simple little design throws the entire outfit off, which is unfortunate given the fact that her hair and jewelry work so well in her favor.

    Savion Washington / Getty Report

    Anna Drever

    3 weeks ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    What’s with the pouty sullen face? It’s not attractive. She’s not bad looking, just quit this sh*t.

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