Editor’s Note: Delving into the archives of pop culture history, “Remember When?” is a CNN Style series offering a nostalgic look at the celebrity outfits that defined their eras.
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A man dances on the top-deck of his private yacht, swigging champagne from the bottle, surrounded by bikini-clad women. He’s heavily fake-tanned, his dark hair is coiffed. But this isn’t a man — it’s Taylor Swift.
Back in February 2020, Swift had not yet announced her Eras Tour (now the highest-grossing tour of all time); released any of the four new records that have come since, or begun re-recording her earliest work. She was, instead, still busily promoting her seventh album, “Lover,” and premiering the self-directed music video for its fourth single, “The Man.”
Throughout the video, and under several pounds of prosthetic makeup, Taylor — appearing in drag as “Tyler” — swans around a boardroom, smokes on the subway, and parties on the private yacht as lyrics lament the double standard between men and women. Tyler is praised for things that real-life Taylor would be shamed for: where she is rude, he is bold; things that make her greedy make him a go-getter. It’s on-the-nose, but it gets her point across.
Peter Kelleher/Victoria and Albert Museum, London
Swift's Versace outfit and facial hair from the video's yacht scene are on display, as well as her director's chair and the MTV Music Video Award for Best Direction.
As well as sporting a wig and faux facial hair, Tyler’s wardrobe as “The Man” features snugly-fitted suits, tennis whites and a brown suede dad jacket. But it’s his gaudy outfit from the yacht that’s been selected for display in a new exhibition at London’s Victoria & Albert Museum (V&A), picked as being definitive of the entire “Lover” period.
“Taylor Swift: Songbook Trail” traces the star’s meteoric journey from childhood to the present day, spreading 13 exhibits of costumes, props and instruments from Swift’s personal archive across the museum’s various galleries.
The centerpiece of Swift’s look from “The Man” is a black, red and gold silk Versace shirt, worn with matching shoes and a pair of white linen Tommy Bahama trousers. Huge black aviator-style sunglasses obscure half of Swift’s face, while hefty gold rings and a gold chain complete the garish look.
“(The costume) is instantly recognizable, and it’s particularly flamboyant,” Kate Bailey, senior curator at London’s Victoria and Albert Museum, told CNN. “It does so much storytelling within that Versace ‘bling’ aesthetic. It speaks volumes — and I never thought in a million years we’d be displaying a beard and facial hair!”
Peter Kelleher/Victoria and Albert Museum, London
The final stop on the trail shows three screens playing videos from Swift's childhood.
But Swift was not the first pop star to don drag for the camera. The members of Queen famously appeared as women in the 1984 video for “I Want to Break Free.” In 2009, Mariah Carey dressed as a male stalker in her “Obsessed” video, while Lady Gaga cast her own campy drag character, Jo Calderone, to star in the video for “You and I” in 2011. Zayn Malik and Troye Sivan have also revealed drag personas on screen (“Best Song Ever” and “One Of Your Girls,” respectively), and Little Mix performed as drag kings in their video for “Confetti” in 2021. As her own alter-ego, Swift is visibly — even through all the makeup — having the time of her life playing the manspreading, leering parallel version of herself.
This era was arguably Swift at her most overtly political. In June 2019 she released her star-studded video for “You Need To Calm Down,” a song celebrating Pride, as well as launching a petition in support of the US Equality Act. “The Man” was a similarly impassioned swing at Swift’s own experiences of sexism during her career. The video came out less than a month after her documentary, “Miss Americana,” which explored similar themes.
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Taylor Swift looks at the crowd at a concert in East Rutherford, New Jersey, in May 2023.
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Swift performs during the "Folklore" set in Chicago in June 2023.
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Fans sing along in Las Vegas in March 2023.
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Swift performs "Lover" with her band, backup singers and dancers in Nashville, Tennessee, in May 2023.
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Swift performs in Glendale, Arizona, during the opening weekend of The Eras Tour in March 2023. Glendale was temporarily re-named Swift City in honor of the concert.
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Swift performs her last show in Los Angeles in August 2023. She was announcing the upcoming release of the album "1989 (Taylor's Version)."
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Glow bracelets light up Acrisure Stadium in Pittsburgh in June 2023.
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Swift performs "22" in Glendale in March 2023.
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Fans in East Rutherford trade friendship bracelets in the parking lot of MetLife Stadium in May 2023.
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Florence Welch of Florence and The Machine joins Swift on stage to perform "Florida!!!" in London in August 2024.
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Fans wait in line to buy tour merchandise outside Raymond James Stadium in Tampa, Florida, in April 2023.
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Swift gives her hat to a fan in Mexico City in August 2023. Each night of the tour, Swift selects one lucky fan to receive a signed hat at the end of her song "22."
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Swift performs "Midnight Rain" in Edinburgh, Scotland, in June 2024.
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Thousands of fans gather on a hill outside a Swift concert in Munich, Germany, in July 2024.
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Swift performs during the "Evermore" section of the show in Sydney in February 2024.
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Fans react outside Lincoln Financial Field as Swift begins her set in Philadelphia in May 2023.
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Swift dances during the "Reputation" set in Atlanta in April 2023.
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Swift twirls during the combined "Folklore" and "Evermore" section of a show in Paris in May 2024.
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Fans show the Ticketmaster queue from the parking lot outside Swift's show in Philadelphia in May 2023.
Ticketmaster apologized to Swift and her fans after a ticketing debacle in November made it difficult to buy tickets when they went on sale.
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Swift smiles at a crowd in Nashville as it gives her a standing ovation for "Champagne Problems" in May 2023.
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Swift opens a show in Lyon, France, in June 2024.
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Travis Kelce, right, joins Swift on stage for
a surprise appearance in London in June 2024. Swift and the three-time Super Bowl champ were first romantically linked in September of last year.
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Swift opens the "Midnights" set with "Lavender Haze" during a show in Glendale in March 2023.
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Swift sings "Look What You Made Me Do" while dancers in Glendale wear outfits from Swift's previous eras in March 2023.
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Swift sings "Who's Afraid of Little Old Me?" in Paris in May 2024.
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Swift performs with the band Haim in Santa Clara, California, in July 2023.
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Swift dances across the stage while singing "August" in Atlanta in April 2023.
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Fans apply jewels on their way to Swift's show in Foxborough, Massachusetts, in May 2023.
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Swift performs during the "Reputation" set in Amsterdam, Netherlands, in July 2024.
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Phoebe Bridgers joins Swift to perform "Nothing New" in Nashville in May 2023. Bridgers was also one of the opening acts.
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Swift performs the "Folklore" set in the rain in Nashville in May 2023. The show was delayed several hours due to storms in the area.
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Swift sings "I Can Do It With a Broken Heart" in Paris in May 2024.
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Swift watches the music video premiere of "I Can See You" in Kansas City, Missouri, in July 2023.
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Fans cheer in East Rutherford in May 2023.
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Sabrina Carpenter joins Swift for the acoustic section of the show in Sydney in February 2024. They performed a mashup of "White Horse" and "Coney Island."
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Swift makes a heart with her hands while performing "Fearless" in Glendale in March 2023.
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Swift and dancers perform during the "Speak Now" set in Sydney in February 2024.
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Fans pose for photos before a show in Melbourne in February 2024.
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Swift performs "The 1" in Chicago in June 2023.
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Swift performs in the rain in Lyon, France, in June 2024.
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Swift and her backup dancers watch the premiere of the "Karma" music video while in East Rutherford in May 2023.
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Swift opens a show in Las Vegas in March 2023.
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Swift wraps her arms around her backup singers, known as The Starlights, during the "Fearless" set in Las Vegas in March 2023.
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Swift announces the release of "Speak Now (Taylor's Version)," a rerecording of her 2010 album, during her show in Nashville in May 2023.
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Swift performs in Houston in April 2023.
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"Swifties" arrive at a metro station temporarily renamed "Speak Now/Taylor's Station" in Inglewood, California, in August 2023.
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Swift performs the 10-minute version of "All Too Well" in Nashville in May 2023.
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Swift leaves the stage after the "Speak Now" set in Nashville in May 2023.
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Backup dancers join Swift during the "Reputation" set in Cincinnati in June 2023.
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Confetti falls as Swift closes a Nashville show with "Karma" in May 2023.
“You are kind of doing a constant strategy in your head as to how not to be shamed for something on any given day,” Swift mused during one scene, filmed while she was writing “The Man.” “But then you get accused of being calculated for having a strategy. You sort of do have to twist yourself into a pretzel on an hourly basis.”
In the years since “The Man” premiered, Swift has released four new albums — plus four re-recordings — but none seem to have inspired the same fledgling political engagement as “Lover” (Before he withdrew from the race, the Biden campaign had hoped, to no avail, that Swift would echo the support she gave him in 2020). Instead, Swift has settled back into the familiar grooves of love, heartbreak, and fringed bodysuits. She does wear a blazer to perform “The Man” on tour — but it’s rhinestoned. At least, with Tyler’s yachting garb on show at the V&A until 8 September, fans can look back on one of the most memorable chapters in Swift’s fashion history.