The singer and “Pose” actor arrived at the ceremony dressed in a custom black and white ensemble by Christian Siriano. The top half resembled a classic tux jacket, complete with a bowtie, while the bottom half ― a full skirt ― was pure drama. (He wore a similar look for the Vanity Fair Oscar party after the awards ceremony.)
Porter’s outfit choice was deeply personal, he told Vogue, saying he has always been interested in fashion but few up feeling “there was a limit to the ways in which [he] could express [himself].”
“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,” he said. “I was trying to fit in to what other people felt I should look like.”
The actor said his role in “Kinky Boots,” for which he won a Tony Award, grounded him in an “unexpected” way.
“Putting on those heels made me feel the most masculine I’ve ever felt in my life,” he said. “It was empowering to let that part of myself free.”
Porter’s past style statements include an embellished silver cape at the Golden Globes and a satin suit with extravagant bow at the Critics’ Choice Awards. See those and more below:
2019
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Daniele Venturelli via Getty Images
Porter wears a Christian Siriano outfit at the 2019 Vanity Fair Oscar Party.
2019
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Santiago Felipe via Getty Images
Porter attends The Blonds fall/winter 2019 runway show at Spring Studios on Feb. 12 in New York City.
2019
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Kris Connor via Getty Images
Porter attends the Blue Jacket Fashion Show benefitting the Prostate Cancer Foundation at Pier 59 Studios in New York City on Feb. 7.
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2019
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Santiago Felipe via Getty Images
Adam Smith and Porter attend the Wan Hung show at Pier 59 Studios in New York City on Feb. 5.
2019
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Santiago Felipe via Getty Images
Porter at Pier 59 Studios on Feb. 4.
2019
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Taylor Hill via Getty Images
Porter attends The 24th annual Critics' Choice Awards at Barker Hangar in Santa Monica, California, on Jan. 13.
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2019
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David Crotty via Getty Images
Porter attends the 76th annual Golden Globe Awards on Jan. 6.
2019
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Rich Fury via Getty Images
Porter attends the Gold Meets Golden party hosted by Nicole Kidman and Nadia Comaneci on Jan. 5.
2019
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Jon Kopaloff via Getty Images
Porter attends the AFI Awards on Jan. 4.
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2018
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Gregg DeGuire via Getty Images
Porter arrives at Out Magazine's OUT100 Awards Celebration on Nov. 15.
2018
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Paul Archuleta via Getty Images
Porter attends the Diversity x Design charity event on Aug. 25, 2018.
2018
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Gary Gershoff via Getty Images
Porter attends the 2018 VH1 Trailblazer Honors on June 21, 2018.
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2018
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Dimitrios Kambouris via Getty Images
Porter attends the Entertainment Weekly and People New York Upfronts celebration on May 14, 2018.
2017
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Gary Gershoff via Getty Images
Porter attends "The Assassination Of Gianni Versace: American Crime Story" New York screening on Dec. 11, 2017.
2017
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Bennett Raglin via Getty Images
Porter attends TDF Honors Broadway's "Kinky Boots" on March 20, 2017.
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2016
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Sean Zanni via Getty Images
Porter attends Netflix Presents the New York Premiere of "The Get Down" on Aug. 11, 2016.
2014
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D Dipasupil via Getty Images
Porter attends the American Theatre Wing's 68th annual Tony Awards at Radio City Music Hall in New York City on June 8, 2014.
Before You Go
Oscars 2019: All The Best Dressed Celebrities
Lady Gaga(01 of47)
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(credit:Steve Granitz via Getty Images)
Letitia Wright(02 of47)
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(credit:Frazer Harrison via Getty Images)
Mahershala Ali (right) and his wife Amatus-Sami Karim(03 of47)
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(credit:Rick Rowell via Getty Images)
Ashley Graham(04 of47)
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(credit:Steve Granitz via Getty Images)
Serena Williams(05 of47)
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(credit:Steve Granitz via Getty Images)
Rami Malek(06 of47)
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(credit:Rick Rowell via Getty Images)
Sarah Paulson(07 of47)
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(credit:Frazer Harrison via Getty Images)
Gloria Campano, from left, Bradley Cooper, and Irina Shayk(08 of47)