The 20 Best- and Worst-Dressed Celebs at the 2021 Oscars

It’s such a Regina King sort of flex to show up at the Oscars in a year when you’re not nominated (but definitely should have been) in a gown that could quite reasonably be placed on the list of Greatest Oscar Gowns of All Time. The One Night in Miami director kicked off the ceremony by strutting through Union Station, clearly feeling her look and projecting confidence, power, and drop-dead stunning elegance.

After a string of subdued, neutral gowns during awards season, the Promising Young Woman star and Best Actress nominee stunned and surprised us by stepping out onto the red carpet in a head-turning metallic gold ensemble with a huge skirt and bandeau top. We appreciated the sudden boldness, but the proportions are a little odd.

Trust Zendaya to make a statement and show up looking like no one else there. If you’re not at the Oscars to pick up a trophy for yourself, it’s a chance to loosen up, have a little fun with the night, and maybe serve a hot look that keeps all eyes on you. We love the light, flowy feel, the gorgeous yellow color, and the beachy waves of her hair. It’s a look for standing in front of a wind machine and of course she worked it to its full effect.

The Promising Young Woman writer/director charmed everyone with her speech, her adorable personality, and a dress that couldn’t have suited her better. She seems to like these flowy, girly gowns a lot, since she’s been wearing them through awards season, but appropriately, this is the best of the lot.

We’ve been saying for years that male stars need to stop dressing like lawyers and butlers on the red carpet and start dressing like the artists they are. Several of the history-making male nominees showed up in stunners, but the Judas and the Black Messiah star and Best Supporting Actor nominee took us back to the disco era in this incredibly cool jumpsuit custom made for him.

At the risk of sounding grammatically unfortunate, H.E.R. always shows up in a look that turns heads by being unforgettably unique. Not only does this dramatic cobalt blue hooded cape paired with round purple shades remind us of Prince (which can only be considered a good thing), but it features the lyrics of her Oscar-nominated song from Judas and the Black Messiah, “Fight For You.” Stylish, unforgettable, iconic, and a fantastic bit of self-promotion to boot.

To win the Oscar, one must become the Oscar. Gold gowns on Oscars red carpets are as old as…well, Oscars red carpets. But the star of The United States vs. Billie Holiday updated that standard with the hottest trend of this year’s ceremony, a massive cutout that gave the look a much sexier and less formal feel. Our only issue is that the textile looks slightly flimsy (although that was clearly the point of it).

The Borat: Subsequent Moviefilm star and Best Supporting Actress nominee has been absolutely crushing it on the style front throughout the promotion for the film and awards season, which is why this somewhat underwhelming, slightly bridal gown feels like a bit of a letdown. It’s pretty, but it may be the least interesting thing she’s worn all year.

He’s lucky he’s so pretty, because it takes a world-class face to pull off that neckline with a tux. Somehow, it works for him, offering up a more modern, slightly minimalist take on classic that suits him really, really well.

If there’s one thing Angela Bassett knows how to do, it’s serve a highly dramatic look. There are, of course, other things she knows how to do, like give incredible acting performances or just stand around being fierce, but in terms of knowing how to step out in something that keeps all eyes on her, this bold red gown with angel wing sleeves can’t be beat.

The Ma Rainey’s Black Bottom star and Best Actress nominee returned to a more classic sort of gown after a string of awards season looks featuring eye-popping silhouettes, bold colors and African prints. But the longer we looked at the beautiful cutout pattern in the bodice, and the way the whole look, from the hair to the skirt, plays with soft and hard elements, the more we fall in love with it.

We really wanted to love this. Reese looks great in red and this gown gives her several shades of it to play with. The skirt is lovely, but the bodice and straps feel a little overworked and the menswear-style belt is an odd and distracting choice. Sorry!

The One Night in Miami star also followed our sage advice about dressing like the Oscar if you want to snag that statue. We love the idea of the suit, but the execution just isn’t quite there. The textile manages to look stiff and wrinkled at the same time and we think the matching gold shirt was a step too far, making him look a little bit like a cross between an Oscar and the Tin Man from The Wizard of Oz.

Oh, no. Someone did Vanessa wrong. In fact, several someones did, judging by the puckered bodice, the color that’s not quite working, and the inexplicably heavy and dark makeup, which doesn’t coordinate well with the dress.

Glenn, we love you and we wish it would just rain Oscars on you for all the incredible performances you’ve given us, but we just can’t love this. If she’d worn an actual salwar kameez, it could have looked incredible, but this version of one by Armani tries a smidge too hard to be a gown and that just doesn’t work once you get to the bottom.

The Ma Rainey’s Black Bottom star kicked off the red carpet and got everyone excited when he stepped out in this gorgeous shocking pink suit with just enough sparkle on it without going overboard. Somehow, despite the glitz and the eye-searing color, it works spectacularly for him. Bubblegum hotness. Is that a thing? It is now.

The Mank star and Best Supporting Actress nominee wore this head-turning gown in a bold red with a big, space-taking silhouette. It’s a look that speaks of Old Hollywood glamour and classic screen siren sex appeal, while also having a sort of confidence and power to it, like she’s staking her claim as an icon. The bust ruffles are a little weird though.

Well, it’s not going to make us forget her iconic Elie Saab gown from when she won the Best Actress Oscar, that’s for sure. Our distaste for the problematic Dolce & Gabbana may be coloring our opinion here, but we don’t love the hue and the design is so generic that she could’ve gotten anyone else to make it for her. The blunt bob was such a surprise that it almost pulls focus, but overall, this look doesn’t work for us.

The star of the upcoming The Suicide Squad and producer of the multiple-nominated Promising Young Woman debuted some really cute soft bangs paired with a simply shaped Chanel rendered in a beautiful silver floral textile. It wasn’t among the showier looks of the night, but it was one of the prettiest and had a quietly chic quality to it—if you can say such a thing about a silver gown.

Last year’s Best Supporting Actress winner came to present in the floofiest, feathery-est skirt we ever saw, although it might look a bit more exuberant than it is because there’s such a disconnect between the tight black top and the massive bottom. It just looks a little too much like an expensive bath rug.