The 21 Best and Worst Dressed Celebs at the 2019 Oscars

By | February 25, 2019

We’ve spent the last two months essentially hanging out with Lady Gaga, Regina King, Olivia Colman, and Glenn Close, and finally we’re at the end of the road: Once the 2019 Oscars are over, all of these actors (and more) can finally take a long, relaxing seat after what feels like eons of promoting their performances. Which of them marked this with personal style bests, and which of them limped to the finish line? We’ve got the answers, from the fancy pants and shimmering capes to the plethora of pink.


Best Surprise: Billy Porter in Custom Christian Siriano

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God bless Billy, who has spent this entire awards season looking profoundly glamorous. He saved the best for last, in the form of this tuxedo ballgown—a phrase we’ve never typed before—and something only he could pull off.

Most Magical: Gemma Chan in Valentino

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Getty ImagesSteve Granitz

Real talk: This dress is a hot pink duvet of a gown. A very fancy bed-in-a-bag. And yet…she looks great in it, somehow seeming casual and easy in what must be 2,000 yards of fabric. We have no idea how she’s managing this, but perhaps she’s interested in teaching a class?

Sassiest Pants: Awkwafina in DSquared

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Getty ImagesRick Rowell

Call it formal disco suiting, if you want to, because that’s what it is—but mostly, we just call it good.

Most Successful at Making Us Eat Our Words: Linda Cardellini in Schiaparelli

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We’d been saying to each other, repeatedly, that Linda’s outfits felt boring during her lengthy stint promoting Green Book. But now we are snacking on a heaping helping of those thoughts. Linda went very big and dramatic at her awards-season swan song, and while her pendulum might’ve swung a tad too far in the other direction—that dress is nearly overshadowing her—we are grateful it moved at all.

Best Cosplay: Sarah Paulson in Brandon Maxwell

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Sarah obviously can carry any dress on her own terms, but tell us this doesn’t look exactly like something stylist Karla Welch would have pulled for fellow client Tracee Ellis Ross, who never met a gigantic pink gown she didn’t love. Now we want to do a deep dive on outfits they’ve each worn that the other might covet. Can we get Ocean’s 9 going with Tracee on board, so they can hit the carpets together more often?

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Best Pink: KiKi Layne in Atelier Versace

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Getty ImagesJeff Kravitz

There was a whole lot of pink on this carpet, in many sizes and flavors, but we absolutely love the authority with which (relative) newcomer KiKi Layne—who starred in If Beale Street Could Talk—cruised onto the red carpet in this lovely number. It’s sleek, cool, and unusual, and makes that pale baby-pink look very grown-up indeed.

Most Divisive: Emma Stone in Louis Vuitton

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Despite our initial unease at Emma’s Vuitton partnership, it does appear that the house is trying to craft some original, unusual pieces for her. Yes, OK, she looks vaguely like a magical Hogwarts creature—her shoulders are a House Elf’s ears, right?—but somehow that isn’t a turnoff for us, thanks to this dress’s appealing texture and unexpected bronze color, and the wisely simple styling around it. But we suspect this one will get some heavy debate at Ye Olde Water Cooler.

Best Slit: Regina King in Oscar de la Renta

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Usually sky-high, thigh-high slits like that make us clutch our phantom pearls like the uptight old crones that we are, but Regina works that thing beautifully—and all the way to Oscar gold. She makes it look graceful and glorious, rather than like an escape route for her left leg.

Most Elegant: Ashley Graham in Zac Posen

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It’s diplomatic to say that historically we haven’t had the most faith in Ashley’s sartorial taste, so this achingly sleek, crisply-cut sheath elicited happy gasps of surprise indeed. From the hair to the jewels to the asymmetrical neckline, it’s absolutely perfect on her.

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Most Minty Fresh: Yalitza Aparicio in Rodarte

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That pale green is a hard color to pull off, but Yalitza looks amazing in it. This dress hails from a design house not typified by its restraint, so bravo to Rodarte for giving this newcomer and first-time nominee not just an unforgettable gown, but an unmissable one.

Most Inspiring (We Hope): Amy Poehler and Elsie Fisher (in Thom Browne)

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Firstly, we love that Elsie’s team put her in suits the entire awards season, befitting both her age and the sense of whimsy that being 14 years old so easily allows. And Amy looks so cool in the grown-up version that we’ve decided we need these two in a project together immediately. Someone please get to work on a mother-daughter comedy.

Most Misguidedly Practical: Rachel Weisz in Givenchy

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Getty ImagesSteve Granitz

It’s rained a LOT in Los Angeles lately, but there was no precipitation in the forecast for Sunday, so we’re not sure why Rachel needed a couture rain poncho. Maybe every year, she ruins her gowns with tears during the In Memoriam tribute?

Strangest: Olivia Colman in Prada

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You know, there are easier ways to give a dress sleeves.

Shiniest: Jennifer Lopez in Tom Ford

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J. Lo may not appreciate people coming up to her to reapply their lipstick by looking at her torso all night, but that’s what you get when you wear what is essentially a mirror. The good news for her is that she looks superb in said mirror, and so she’ll be fielding compliments all night while people are staring at their own reflections.

Most Like an Actual Oscar: Glenn Close in Carolina Herrera

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Conventional wisdom says you don’t dress like an Oscar unless you’re sure it’s coming home with you, but our rule of thumb is that you basically never can lose wearing a gold lamé cape.

Most Organized: Marie Kondo

Like we weren’t going to make that joke. (Having made it, though, she looks great. Maybe we should clean out our closets. What if the likes of this lurks inside?)

Most Regal: Michelle Yeoh in Elie Saab

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There’s so much we’re going to miss now that the Crazy Rich Asians press tour has well and truly concluded, but most of all—even more than Henry Golding’s face—we are lamenting the upcoming break in seeing Michelle on red carpets looking perfect from top to toe. At least she’s gone out on this perfect high.

Biggest Flop: Charlize Theron in Dior

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Getty ImagesJeff Kravitz

Well, her face looks great—she is still Charlize Theron, after all. Her jewelry is also fantastic! There’s a lot to praise here, is what we’re saying. But absolutely none of that applies to her dress, which is a dingy color, severe fit, and less than the rest of her deserves.

Boldest Throwback: Constance Wu in Custom Versace

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This is heavily reminiscent of another famous Oscar gown—namely, Vera Wang’s mustard-yellow number that Michelle Williams wore in 2006, which even has its own Wikipedia page—but at least Constance is giving it her own great oomph.

Most Dressed for a Dramatic Wake: Lady Gaga in Alexander McQueen

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Going into awards season, some wondered if January and February would be a coronation for Lady Gaga, Serious Actress. It hasn’t turned out that way, though—and thus it’s hard NOT to see this as Gaga’s final farewell to A Star Is Born, before, we hope, ripping off her gloves and swatting someone with them. (Is there any OTHER reason to wear gloves?!) Having said that, this dress is a good mix of Classic Gaga with Gaga 2.0, and we applaud her for striking that balance as she transitions into whatever is next.

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