Billy Porter wears custom Christian Siriano to the 91st Annual Academy Awards on February 24, 2019 in Hollywood, California.
Photo: Frazer Harrison (Getty Images)

It started with a ball gown. It may not have been an unusual choice for the red carpet of the Academy Awards, but its wearer wasn’t the usual starlet or ingenue. When Broadway and television star Billy Porter appeared wearing a black velvet ball gown with a traditional tux top, it was clear it would be a night for breaking boundaries—and aside from a sadly pandering choice for Best Picture (Green Book? Really?), for once, the Oscars didn’t disappoint.

Regina King, in Oscar de la Renta, poses in the press room with her Best Supporting Actress Oscar.

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Take the queen of the night, Regina King (or as we like to call her, “Queen King”), who was celebrated early in the night with a Best Supporting Actress win for her incredible work in If Beale Street Could Talk. Styled by Wayman and Micah, who also dressed costar KiKi Layne and Tessa Thompson last night, King looked every inch the winner Sunday night in a strapless ivory Oscar de la Renta gown with a draped waist and sky-high slit. Paired with jewelry from Chopard, pearlized Louboutins and a blunt wavy bob, King proved that classic Hollywood glamour comes in caramel, too.

Speaking on her breathtaking performance and well-deserved win, King reflected not only on Beale Street author James Baldwin but the impact of the Me Too Movement on her approach to character Sharon Rivers’ pivotal scene. King rightly even evoked the first black Academy Award winner Hattie McDaniel, who won the same category nearly 80 years ago, in 1940.

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“[I] feel like I’ve had so many women that have paved the way, are paving the way, and I feel like I walk in their light, and I also am creating my own light,” King told the press room. “And there are young women that will walk in the light that I’m continuing to shine and expand from those women before me.”

Two black women who shone alongside King last night were Black Panther costume designer Ruth E. Carter and production designer Hannah Beachler, who each became the first black woman to win their respective categories at the Oscars.

Ruth E. Carter (l) and Hannah Beachler pose in the press room.
Photo: Frazer Harrison (Getty Images)

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“I dreamed of this night. I dreamed of this night and I—I prayed for this night honestly,” Carter said of her win, more than three decades and three nominations in the making. “Not only just for being a hard‑working costume designer but what it would mean for young people coming behind me, because, you know, this came from grassroots, you know. I started with an independent film with Spike Lee, and it rose through 40 films, 50 films and two Oscar nominations without a win. But I dreamed of this night. And now I hope that now I won’t—we won’t necessarily have to wait for another first. We have the first.”

Lee, also a winner last night (for Best Adapted Screenplay), was on hand to see his longtime collaborator finally win her deserved Oscar—which follows a recent Black Panther win and Lifetime Achievement Award from the Costume Designers Guild. Notably, Carter’s regal Oscar gown was a collaboration with fellow black designer B. Michael, who also dressed Cicely Tyson for the awards ceremony (and accompanied Ms. Tyson as her date for the evening).

But while Carter and Beachler were making Oscars history in their categories, this year also marked the first time more than one black woman has won an Oscar in a single year. In fact, Black Panther’s visionaries are only the second and third black women to win non-acting Oscars in the 91-year history of the awards ceremony.

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But back to that ball gown. Porter, who memorably wowed onlookers with a hot pink satin-lined cape at this year’s Golden Globes, knew he wanted to up the ante for the Academy Awards, where he was one of this year’s red carpet hosts. And after acting as men’s fashion ambassador during New York Fashion Week, Porter knew just the designer he wanted to work with: red carpet and equal opportunity fashion favorite Christian Siriano.

With less than two weeks between Siriano’s Fall/Winter runway show and the Oscars red carpet, the designer crafted a gender fluid vision from Porter’s last-minute request for a custom ball gown.

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“I’ve always wanted to wear a ball gown, I just didn’t know when,” Porter told Vogue, speaking about the inspiration and process. “[Siriano and I] wanted to play between the masculine and the feminine. This look was interesting because it’s not drag. I’m not a drag queen, I’m a man in a dress. He came up with a tux on the top, and a ballgown that bursts out at the bottom.”

To ease Porter’s mobility (and not distract from his celebrity guests), Siriano included a day-to-night option; though Porter wowed on the carpet in his gown, he wore a tuxedo and palazzo pants to conduct interviews. But if it seemed Porter had once again outdone himself with an over-the top fashion moment, the choice was also more than a little political.

I grew up loving fashion, but there was a limit to the ways in which I could express myself. When you’re black and you’re gay, one’s masculinity is in question. I dealt with a lot of homophobia in relation to my clothing choices. ...

Now I’m in a space where, being on Pose, I’m invited to red carpets and I have something to say through clothes. My goal is to be a walking piece of political art every time I show up. To challenge expectations. What is masculinity? What does that mean? Women show up every day in pants, but the minute a man wears a dress, the seas part. It happened to me at the Golden Globes [when I wore a pink cape], and I was like, really? Y’all trippin’? I stopped traffic! That Globes outfit changed everything for me. I had the courage to push the status quo. ...

[At the first fitting in the gown,] I felt alive. I felt free. And open, and radiant. And beautiful! Which has not always been the case for me. I haven’t always felt so good about myself. ... People are going to be really uncomfortable with my black ass in a ball gown—but it’s not anybody’s business but mine.

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And while the Oscars red carpet was full of big designer moments, there was one beautiful accessory that seemed to be on many celebrities’ arms last night, as many brought their mothers as their dates. In fact, black moms were in abundance last night; both KiKi Layne and Michael B. Jordan brought theirs onto the red carpet, while Ruth Carter shouted out her 97-year-old mother from the stage, calling her “the first superhero.” And memorably, Regina King tearfully pointed hers out in the front row as she accepted her award.

(L-R) Sandra Layne and KiKi Layne; Donna Jordan and Michael B. Jordan
Photo: Kevork Djansezian (Getty Images), Frazer Harrison (Getty Images)

“It’s hard to, like, put it in words really quickly,” King told the press room of her winning moment. “I feel kind of like one of those full circle moments because so much of the character Sharon Rivers was mapped or inspired by my mother and my grandmother. So to have her there ... it goes by so fast, and you want to thank so many people, and your mind just goes blank. And, you know, my mom was like the lighthouse right there. And ... mmm, just everything.”

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“Everything” is certainly how we felt seeing the gorgeous array of blackness on Sunday’s red carpet—from Amandla Stenberg in delicately chain-fringed Miu Miu with braided finger waves to Serena Williams looking snatched in custom Armani Privé. And mere days after the death of Karl Lagerfeld, both Tessa Thompson and Lisa Bonet wore sartorial tributes to the designer, Thompson in black and gold Chanel and Bonet and husband Jason Momoa wearing Lagerfeld’s eponymous line in the color of the night: pink. And Porter wasn’t the only one blurring the lines on typically binary fashion; Chadwick Boseman continued to be both Afro-futuristic and fashion-forward, wearing a beaded tux with flowing tails by Givenchy atop a tie-neck black silk shirt.

As always, we’ve compiled the best and blackest looks from the Oscars red carpet. See who had the most winning looks last night—and see if you can spot the Black Panther cub on the way!