Remember when Taylor Swift wore drag in ‘The Man’ music video

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.

CNN
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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.

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!”

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.

“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.