October 01 2025, 08:15 
Immediately after Puerto Rican reggaeton artist Bad Bunny was announced as the halftime show performer for the 2026 Super Bowl, right-wingers began trying to “cancel” the cis-het ally by pointing out his refusal to sing in English and his past performances in drag.
Bad Bunny — who grew up in a lower-middle-class barrio near Puerto Rico’s small coastal city of Vega Baja — has always subverted gender norms and expressed his queer-friendly political identity by incorporating masculine and feminine elements into his flashy fashions (which have included bright colors, oversized garments, and eye-catching accessories). But five of his public appearances specifically made headlines for their gender-bending appeal.
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Here’s a quick look at these five instances, along with a brief exploration of how they reflect the long queer history of Puerto Rico’s drag and gender-bending performers, and how both have sought to express and transcend the island territory’s complex political relationship with the United States.
Fashion activism
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During his February 2020 performance on The Tonight Show, Bad Bunny performed while wearing a large pink blazer and black skirt.
Later on in the show, he revealed a t-shirt that said, “Mataron a Alexa, no a un hombre con falda,” (“They killed Alexa, not a man in a skirt”). The t-shirt referenced the murder of Alexa Negrón Luciano, a homeless transgender woman in Puerto Rico, who the police report misgendered as a “man dressed in a black skirt.”
A red leather minidress and flawless wig
The music video for the song “Yo Perreo Sola” (“I Twerk Alone”) — released in March 2020 — featured Bad Bunny in a red leather minidress and flawless wig, portraying a sexy woman who really just wants to be left alone to dance by herself at a club.
Later on in the video, he dresses as a long-haired woman whose bright floral outfit accentuates her breasts and buttocks.
Poolside photo shoot in heels
In a February 2022 fashion shoot for the indie luxury brand Jacquemus, Bad Bunny wore a pink dress, pale blue high heels, and other poolside fashions in Miami, an area with a population of 3.7% Puerto Rican descent.
An iconic cover story
In August 2022, Bad Bunny graced the cover of “The Icons Issue” of Harper’s Bazaar magazine in a white tuxedo top and a long white skirt while wearing white, thick-soled workboots and small white earrings.
In his interview with the magazine, he explained, “I always remember seeing the pieces in women’s clothing and they would always fit me so much better and they had so much different variety… I don’t [dress this way] to become more famous or to call attention or to disrespect anyone. People on the outside can think that I have a strategy or I wear this to call for attention, but in reality I just know who I am.”
“Obviously, as you get older, you start seeing what the world shows you, and if I lived my life that way, then I wouldn’t be able to dress in the way that I really want to,” he said, adding that his success and fame have given him the freedom to explore his personal style. “I’m taking advantage of this moment in my life when I can do whatever I want and wear what I want, so I get to live life more authentically.”
Floral elegance at the Met Gala
Bad Bunny showed up at the May 2023 Met Gala wearing a white double-breasted suit – backless, as if it were an evening gown – with a 20-foot-long train of white flowers draped around his shoulders.
Bad Bunny’s drag and gender-bending fashions are part of Puerto Rico’s queer political history
Puerto Rico’s drag and gender-bending performers have long used fashion to explore the island territory’s complicated social politics and relationship with the United States.
The island has hosted influential drag and gender-bending performers since the 1960s, with local icons, like trans performer Lady Cataria, presenting regal pageantry and dancing the Bomba, a traditional Puerto Rican dance with African roots, according to Louie Ortiz-Fonseca.
One of queer history’s most famous queens, Stonewall veteran Sylvia Rivera, was half-Puerto Rican and half-Venezuelan. Born in New York City, she advocated for trans people, sex workers, incarcerated queer people, and other marginalized members of the community that more “respectable” white gays and lesbians at the time seemed eager to hide away.
In the modern era, several Puerto Rican queens have participated in RuPaul’s Drag Race, including Nina Flowers, Yara Sofia, Alexis and Vanessa Vanjie Mateo, Alyssa Hunter, and Cynthia Lee Fontaine; several have even drawn large crowds at San Juan’s queer nightclubs.
“‘In this way, the body becomes the main textual terrain for the exploration of issues and politics related to politics, subjectivity, nationality, sexuality, and aesthetics, among many others.”
– Puerto Rican critic Gilberto Blasini
In various ways, these performers have centered their Puerto Rican and Caribbean roots to re-affirm their cultural identities in the face of the American colonialism that has contributed to the island territory’s growing debt, infrastructural decay, and gentrification, all of which have pervaded Puerto Rico since the U.S. first seized control of it in 1899, according to gay Puerto Rican author Lawrence La Fountain-Stokes.
La Fountain-Stokes has helped popularize the term transloca as a way to discuss the numerous ways that drag and queer performers have tried to transcend U.S. influence over the island while also transforming political space around them.
As he explained in his his 2020 book Translocas: The Politics of Puerto Rican Drag and Trans Performance, the word loca has long been friendly or pejorative slang that either refers to “crazy females” or effeminate gay men.
La Fountain-Stokes coined the term transloca to include drag performers and trans women activists as a way of examinining how drag and trans art are “a form of entertainment, a catalyst for community growth, and a mechanism of self-expression” that also embody the complexities of Puerto Rican race, gender, sexuality, class, and migration — especially as the territory grapples with its own history of anti-LGBTQ+ violence.
As is happening across the U.S., anti-LGBTQ+ politicians in Puerto Rico have tried to ban drag as an “obscene” threat to children. Simultaneously, the island territory has also experienced its own instances of anti-LGBTQ+ violence, against which Bad Bunny and other local performers have spoken out, through their fashionable performances.
“Translocas are many things, contradictory ones, to be sure: performers, queers, innovators, marginals, exiles, eccentrics, beauties, troublemakers, lovers, loners, friends,” La Fountain-Stokes writes. “The performer/protagonist has to negotiate multiple preconceptions in the very formulation of who he is and how he presents himself—and the profound instability of that in a homophobic, racist, and classist environment, ones that can easily lead to translocura (transmadness).”
“‘In this way,” the author adds, quoting the Puerto Rican critic Gilberto Blasini, “the body becomes the main textual terrain for the exploration of issues and politics related to politics, subjectivity, nationality, sexuality, and aesthetics, among many others.”
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