The Best, Worst, and Most Absurdly Over-the-Top Looks From the 2020 Grammys (2024)

red carpet derby Jan. 26, 2020

By Sarah Spellings

The Best, Worst, and Most Absurdly Over-the-Top Looks From the 2020 Grammys (1)

FKA Twigs, Ariana Grande, and Tyler, the Creator. Photo: Getty Images

At award shows like the Oscars, the Emmys, and even the Golden Globes, the red carpet tends to be a sea of grand dresses. Those can be glorious in their own right, but they get monotonous after a while. So thank the yeehaw gods for the Grammys, which are often a fun red carpet but were even more fun tonight than most. Yes, Ariana Grande did wear a tulle ballgown (she looked great) but everyone else brought out their most unlikely gear: face masks and cowboy hats and giant pink suitcases, patterned suits and pearls and one water bottle nestled in a Chanel purse. Scroll down for our list of the best, worst, and most over-the-top looks from the 2020 Grammy Awards.

Best Automated Hat: Billy Porter

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Billy Porter. Photo: VALERIE MACON/AFP via Getty Images

Yes, yes, another Billy Porter mention on the best-dressed page. This time, instead of riding in on a litter carried by bare-chested men or wearing the curtain from his hit play, he channeled musicians like Sia and Orville Peck with a face-obscuring hat. When it was time to reveal his face to the camera, the fringe parted automatically. What a performance.

Most On-Brand Outfit: Billie Eilish

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Billie Eilish in Gucci. Photo: Amy Sussman/Getty Images

Billie Eilish has a set look. We expect her to wear something oversize in neon green and black. What’s impressive is how many permutations of this outfit she manages to find. This Gucci ensemble is especially nice because of the fingertip-less gloves which show off her manicure, and the bejeweled face mask.

Best Harness: Lil Nas X

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Best Theater Kid: Ben Platt

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Photo: Frazer Harrison/Getty Images for The Recording A

Look, all I’m saying is that this is exactly how the guy who was obsessed with Sondheim in eighth grade would dress given the chance to go to the Grammys. Platt is also probably that guy!

Best Neck Accoutrements: Diplo and Orville Peck

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Diplo in Ralph Lauren Purple Label and Orville Peck in Dior. Photo: (C)Kevin Mazur/Getty Images for The Recording A

The men of the Grammys were really competing for the best cowboy hat. Diplo and Orville Peck may not have won that race, but they did have the best ties — Peck’s was a true bolo tie, while Diplo’s had a turquoise pin. They’re definitely … going for it.

Best Ballgown: Ariana Grande

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Ariana Grande in Giambattista Valli, styled by Law Roach. Photo: Amy Sussman/Getty Images

There had to be one big dress, right? There always is. But Grande’s is interesting because it’s a rather somber shade of gray. The effect is arresting and also a little melancholy. She posed sitting into her dress, letting the cloud poof up around her while she pressed her gloves to her face.

Most Likely to Be Waiting for Her Husband to Return From the War: FKA twigs

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Best Patterned Suit: Brandi Carlile

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Brandi Carlile styled by Maryam Malakpour. Photo: Frazer Harrison/Getty Images for The Recording A

It was tough competition out there for people wearing suits, but Brandi Carlile’s brocade suit was the best one with a pattern. In keeping with the unofficial country theme of the night, she wore Western-ish booties with the suit, and a shirt with a wide, ’70s collar.

Most Wes Anderson: Tyler, the Creator

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Tyler, the Creator. Photo: Amy Sussman/Getty Images

Red carpets are all really performance art, aren’t they? Tyler, the Creator’s Grand Budapest Hotel get-up is just leaning into it. It’s also definitely going to be memed.

Best Glam: Lizzo

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Lizzo in Versace. Photo: Amy Sussman/Getty Images

Lizzo is nominated for the most Grammy awards of anyone tonight — eight in total. It’s her night. She dressed the part in an old Hollywood-inspired white dress and matching fur stole.

Highest Tax Bracket: BTS

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BTS in Bottega Veneta. Photo: Emma McIntyre/Getty Images for The Recording A

The K-pop group might not look like they’re heading to a red carpet, but they do look rich. All of them are wearing neutral Bottega Veneta outfits, and seven of them are in turtlenecks.

Best Pearl Accent: Shawn Mendes

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Shawn Mendes. Photo: Amy Sussman/Getty Images

We’ve seen some good jewelry tonight, but I’m partial to Shawn Mendes’s chain with a little baroque pearl on the end. Very dapper. Very Harry Styles.

Most Talked-About Accessory: Maggie Rogers

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Maggie Rogers in Chanel. Photo: VALERIE MACON/AFP via Getty Images

Maggie Rogers looked fabulous in her Chanel dress, but what was most discussed was the water bottle (I think a Klean Kanteen) in her purse. It feels a little gimmicky — VSCO girl comparisons swiftly followed — but Rogers does seem like the kind of person to carry a water bottle everywhere, so, proceed.

Best Suiting Surprise: John Legend

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John Legend. Photo: VALERIE MACON/AFP via Getty Images

Compared to the other suits on the red carpet, the right side of John Legend’s suit really is nothing special. But the left, with the long pleated skirt, is. Legend often favors pastel suits on the red carpet, but this is a nice new twist.

Most Satisfying ’90s Nostalgia: Dua Lipa

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Dua Lipa. Photo: Amy Sussman/Getty Images

America needs a new girl band to worship. But in the meantime, Dua Lipa is giving ’90s girl-band vibes with blue eyeshadow, a bare midriff, and a creative half-up, half-down hairstyle.