Bad Bunny walks into a conference room at the Fontainebleau hotel in Las Vegas in incognito mode—brown thermal hoodie, hood up, over a logo-less navy baseball cap and wraparound black sunglasses. But when he takes his glasses off and makes his way to the head of the table with a cup of coffee—three shots, oat milk, sugar—he quickly becomes Benito Antonio Martínez Ocasio, the 31-year-old Puerto Rican superstar who has fully owned all of 2025 since releasing his sixth studio album, Debí Tirar Más Fotos, in January. The day after we chat, he will win five of the 12 Latin Grammys he was nominated for this year—including album of the year—though he is already in a state of euphoria. “I’ve just done a historic fitting,” he says, as he takes a seat, fresh from a couple hours of putting together looks with his longtime stylists Storm Pablo and Marvin Douglas Linares.
“I still don’t know what I am going to wear tomorrow,” he says, “but it’s been a long time since I’ve had so many options that I loved, and where I had so much fun,” he adds. At the ceremony, he ends up wearing a black Loewe suit composed of a double-breasted jacket and slightly slouchy trousers, a tight-fitting white button-down shirt (done all the way up, no tie), a logo’d cream baseball cap from the independent label Shapes, black thick-rimmed aviator glasses, and a flower brooch on his lapel; later, for his performance, he changed into a plaid hoodie from the Los Angeles label 424, an Elder Statesman scarf, ERL shorts, and his own Adidas boxing-style sneakers, rumored to be part of an upcoming drop from his ongoing collaboration.
While Benito has always taken great care with what he wears, there is a touch of magical realism to the way he describes his process of putting together outfits. “There was a specific look that I took a long, long time to discover,” he says, “and just when I was about to give up and call it quits—that’s when the outfit arrived.” He continues: “I can compare it to writing a song—when you feel the energy and you change one thing and put in something else, then you take that off and put in a different thing and you start seeing it come together; suddenly, something really cool appears.” The look (which, in the end, he didn’t end up wearing to the ceremony) included Storm’s personal ’90s-style headphones and vintage Herman Miller bag—replete with his embellished key chain and car keys. An image appears in my head of Benito as the Tasmanian Devil from Looney Tunes, tearing through racks of clothes and tables full of accessories, caught up in a creative frenzy that sucks in everything and everyone around him.
At one point in our interview, life imitates art when Benito says he likes the rings I am wearing and asks if he can borrow them for a day—though, sadly, they don’t fit. Undaunted, he snaps a photo to send to Storm and Marvin. “He always knows what he wants to do,” Storm explains to me later. “His biggest thing—and we feel the same way—is not looking like a mannequin.”
Stylists or no stylists, “I don’t like it when I don’t feel like I’ve dressed myself,” Benito says. One gets the impression that, in the end, he does whatever he wants anyway. “He has a very good idea of who he is,” Storm says.
That self-assurance was there from the beginning. “I had another friend who was a singer,” recalls Janthony Oliveras, who now works as his creative director, “but when I first heard Benito’s music, I understood that there was a big difference between them—I understood the talent.” The two, who knew each other from high school, reconnected when Benito was in college. “At first I was his manager—sold the parties, made sure we got paid—and promoter,” Janthony says. “I was even his DJ at those first few parties, even though I know nothing about it.”
Benito wasn’t, however, always so creative when it came to getting dressed. “When we first started he was kind of low-key—a pair of jeans and a good pair of sneakers,” Janthony recalls. “We had a low budget, but he had a pair of red Reeboks that were kind of chunky—they weren’t the kind of shoes you would usually wear so they felt very like, These are artist sneakers—and he would always wear a little bandanna tied around his head, kinda like Tupac.”
Benito was 22 years old, working at an Econo grocery store in his hometown of Vega Baja, when the songs he’d been uploading to SoundCloud first started gathering attention. By the time X100Pre, his first album, came out two years later on Christmas Eve 2018, he had already established himself as The King of Latin Trap, with over a dozen songs on the Billboard Latin Charts, a feature on Cardi B’s chart-topping “I Like It,” and a world tour that took him to the United States and across Latin America and Europe. “Everything started growing so fast,” Janthony remembers.
It hasn’t stopped since. Every album he’s released since 2020’s El Último Tour del Mundo has topped both the American and Latin Billboard charts. He’s been Spotify’s most-streamed artist multiple times, including during a year (2021) when he didn’t even release a new record, and 2022’s Un Verano Sin Ti was the first album by a Latin artist to be streamed over 10 billion times. Benito also began moonlighting as an actor, showing up in Netflix’s Narcos: Mexico, in Bullet Train opposite Brad Pitt, in Darren Aronofsky’s Caught Stealing alongside Austin Butler and Zoë Kravitz, and in Happy Gilmore 2 with Adam Sandler; he’s shown a talent for comedy with appearances on Saturday Night Live (he’s hosted twice); and he set his sights on conquering the WWE—as both a fiercely dedicated fan and a title-holding wrestler, quickly becoming a fan favorite thanks to his dedication to mastering the sport’s most difficult moves.
By the time Debí Tirar Más Fotos was released in early January, he’d become a global superstar, with the album going number one in the Americas and far beyond. He’s now about to embark on a sold-out international tour, and in September he was announced, with no small amount of fanfare, as the headliner for the 2026 Super Bowl halftime show—the first to be performed almost entirely in Spanish: the biggest music star in the world on one of the biggest stages in the world. (When pressed about it, though, he stays resolutely mum about any plans, predictions, hopes, dreams: “I know something’s happening, but I don’t know exactly what’s going to happen,” he says, with a devilish grin.)
As is often the case with Benito, every aspect of his artistry has meaning. And from the earliest promotional appearances, it was obvious that the clothes he was wearing were the sartorial equivalent of Debí Tirar Más Fotos: a concept album about Puerto Rico and puertorriqueñidad which gathered influences as diverse as the jíbaro music of Chuíto el de Bayamón (one of the most important figures in Puerto Rican music), the salsa clásica of the 1970s (born from Puerto Ricans and other Latinx immigrants who had settled in New York City), and contemporary reggaeton. There were classic white tees worn with wide-leg stonewashed jeans held up with a rope tied around his waist like a belt, the way jíbaros who lived in the mountains of Puerto Rico in the 19th century used to wear them; leather flip-flops, or chancletas metedeo (in the ’80s and ’90s, the most ubiquitous version of them had PUERTO RICO burnished in bronze on the thong); ’70s-inspired double-breasted suits with creased trousers like the salseros used to wear; and the mix-and-match sportswear central to the way young Puerto Ricans dress now. Together, it all forms a timeless snapshot of the island’s culture—past, present, and future.
Still, it was only this summer, at his 31-show residency at San Juan’s Choliseo, where, in-between his homages to the Fania All-Stars and the jíbaro, we caught a glimpse of where Benito the person meets Bad Bunny the artist. It was during the concert’s second act—staged at La Casita, a full-scale house that mimics the concrete homes found in the countryside throughout the island built inside the venue and inspired by classic parties de marquesina (house parties)—where, each night, his personal style truly came alive. “That was the most fun,” he remembers now. “We literally had a closet full of clothes, and every Friday [the shows took place on Fridays, Saturdays, and Sundays], I would put together the weekend’s outfits. It was a very playful process, because sometimes I would think, Oh—this is how I used to dress back in the day. It was very freestyle.” At La Casita, Benito experimented with a vintage T-shirt accessorized with a random silk tie thrown over it, denim overalls, Puerto Rican flag satin shorts, and other pieces that could very well have come from his own closet: colorful hoodies, basketball jerseys, baggy denim shorts, and even a plaid skirt, all grounded with colorful Adidas from his collaboration with the sportswear giant.
The shows also engendered an explosion of style experimentation among the audiences—who, inspired by Bad Bunny’s reclaiming of Puerto Rican culture, showed up in pavas, rocking their flag’s colors, or even in recreations of Benito’s Met Gala look. “People have always loved to dress up for my shows,” he says, “and this was definitely the [record] that lent itself to more creative interpretations—I could see it all bubbling up on social media,” he says. Soon after Debí Tirar Más Fotos came out, fans took to Instagram to share photos of themselves in Puerto Rican costume—often from elementary school cultural celebrations—with captions declaring they’d found their concert ’fits. “Seeing all the diversity at my shows,” Benito says, “from young to old, all the creativity…. Some people dressed up as jíbaros: Everyone interpreted Debí Tirar Más Fotos, and what it means to be Puerto Rican, in their own way. It was one of the things that impressed me the most and that I enjoyed the most.”
If, at the very beginning of his career, it was his music that made people stop and pay attention, his emerging style signaled that this was a completely different artist. He famously wore a boldly printed yellow floral Gucci suit by Alessandro Michele for his first major red carpet appearance, and his penchant both for experimentation and for crossing genres soon became a musical signature in addition to a sartorial one—see the cheeky pop-punk rhythms of “Tenemos Que Hablar” on his debut album. (“The Gucci thing was all him,” Janthony says with a chuckle. “It was those first moments where he was making good money, and we were both real fans of [Latin rapper] Arcángel at the time, and he had a song, ‘Gucci Boys Club,’ so it was like: Damn—it’s Gucci!”)
Though Benito claims to not have a favorite designer, there are a few likely candidates: There’s Michele, now at Valentino, whose clothes Benito has worn throughout the years; Simon Porte Jacquemus, who created the iconic backless suit he wore to attend the 2023 Met Gala (Benito also starred in an ad campaign for the French designer last year); and the American label Bode, long one of his go-tos, with Emily Adams Bode Aujla even creating custom suits for last year’s Most Wanted Tour. (In his downtime, he can often be spotted wearing a pair of jeans from Sky High Farm and his own Adidas sneakers and sandals.)
“I know, like, four designers,” Benito says with a laugh, though the key to his style isn’t a label or a designer—it’s Janthony. “He’s the person I connect with the most,” Benito says. “Even when I was putting together all the outfits for La Casita, the person whose approval I always seek is his.” If, when he was younger, he had the bad habit of shopping and then leaving the new clothes to languish in his closet, unworn and with the tags still on, he’s since changed his ways. “That’s something that I learned from Jan—that if I buy something, I need to wear it right now. You can’t save things for a special occasion.” Janthony seconds the thought. “We’re living a special life,” he says, “so let’s dress up whenever we can.”
But in a year full of superlatives and accolades—there are also six more Grammy nominations (he has three trophies already), including for album, song, and record of the year—Benito is staying resolutely humble about the idea of being one of Vogue’s best-dressed. “It’s a cool thing,” he says, “because the people that chose it liked what I did this year, but it doesn’t make me the best-dressed person on earth.” Who would that award go to? He thinks for a good long while, and then says: “I’ll pick someone who never failed during all 31 of my residency shows, and they did it without a stylist: Mami.”
In this story: grooming, Gilbert Gonzalez; tailor, Kyle Kasabuske.
Produced by Modem Creative Projects. Set Design: Colin Phelan.
Special thanks to Westgate Las Vegas Resort Casino.
See more of Vogue’s Best Dressed 2025 coverage here.
