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From the sandy shores of Puerto Rico to the concrete streets of “NUEVAYoL,” all the way to Levi’s Stadium in Santa Clara, California, for Super Bowl LX, Bad Bunny knows how to keep the fashion world hopping.
He’s a constant paragon of Latin American culture, but the reggaeton rapper’s wardrobe is forever changing — ranging from the outlandishly outré to the ornately opulent.
It’s a what-will-he-wear-next flex that has fashion aficionados on the edge of their seats, hotly anticipating whichever wild style Bad Bunny — née Benito Antonio Martínez Ocasio, 31 — will don while headlining the 2026 Apple Music Super Bowl halftime show, where the Seattle Seahawks and the New England Patriots face off on Sunday.
His is the classic Cinderella story.
Metamorphosing from a wannabe in 2016 to a six-time Grammy winner — including this year’s landmark Album of the Year trophy for “DeBí TiRAR MáS FOToS” — Bad Bunny’s star and swag have both skyrocketed to haute heights during the past decade.
The evolution has earned him work with major labels — from Calvin Klein and Adidas to the swank likes of Jacquemus and Gucci.
It also landed the virtuoso on the cover of Vogue’s “Best Dressed 2025” this past December.
“Bad Bunny’s style is fun and androgynous — a perfect mix of masculinity and femininity wrapped in Puerto Rican pride,” Chris Garces, a Big Apple-area fashionista, explained to The Post.
The keep-’em-guessing vibe can be divisive — fans of singer George Strait recently launched a petition demanding the country icon be given Super Bowl halftime show honors, as Bad Bunny’s “drag performances and style are the opposite of what families expect on football’s biggest stage.”
But Drew Thomas, a NYC fashion influencer, predicts that Bunny’s game-day attire will be more godly than ghastly.
“I fully expect something very heavenly-body themed — all white, bright and eclectic,” said Thomas. “His style sets him apart because it’s bold, fluid and pushes boundaries.”
Garces agrees, saying, “I think his Super Bowl look will be a unisex love letter to Puerto Rico. It’ll inspire a new wave of 2026 trends.”
It’s a forecast with history on its side.
Kendrick Lamar ignited a denim wildfire after taking center stage in $1,200 flared Celine jeans during Super Bowl 2025. Immediately after the event, sources close to Celine in SoHo exclusively told The Post that bottoms had “completely sold out,” thanks to the “Not Like Us” rapper’s NFL showcase.
So, it’ll be fascinating to see which fashion fads Bad Bunny triggers as this year’s mid-game MVP.
Here’s a look at the “NUEVAYoL” rhymer’s most voguish moments — from his humbler, early era to the chart-topping, conversation-dominating present.
Petal to the medal
Hitting an A-list red carpet just months after hit track “Diles,” took the internet by storm, Bad Bunny wowed in a yellow floral print suit with black embroidered lapels by Gucci for the 2017 Latin American Music Awards.
The ensemble was made complete with a pair of the Italian label’s L’Aveugle Par Amour rounded sunglasses, red dress shoes and a nor’easter of icy jewels.
His look was a tastefully elevated departure from the studded denim jacket and distressed skinny jeans he’d worn to the Billboard Latin Music Awards earlier that year.
Color me obsessed
Performing at Madison Square Garden is a musician’s dream come true.
And for his fantasy-turned-reality moment in 2019, Bad Bunny sent eyes popping in an iridescent overcoat, featuring a bubblegum pink sheen, to complement his tennis ball-green hairdo.
The Puerto Rican peacock flaunted the flashy fashion during his “X 100Pre” tour — eponymously named after his debut album.
The cherry-on-top — more like on fingertips — were the emcee’s medium-length, almond-shaped acrylic nails, which served as a stylish thumb-to-the-nose of gendered beauty norms.
The belle of the Bowl
Sharing the spotlight with VIPs Shakira and Jennifer Lopez is not for the timid.
Luckily for the “Callaíta” crooner, both his talent and tailor-made gear gave him an extra measure of confidence to rock the Super Bowl LIV halftime stage alongside the Latina divas in 2020.
The bright lights danced across Bad Bunny’s customized “laser technical vinyl coat,” encrusted with 13,000 hand-selected, hand-sewn Swarovski stones by Berlin-based brand Last Heirs.
The sparkly spectacle was paired with silvery trousers and a matching pullover, plus a pair of Nike Blazers that were covered in Swarovski bling, too.
It’s a look-at-me look that Señor Bunny is sure to outdo as kingpin at this year’s big to-do.
In mint condition
Bad Bunny blew fans away by ditching his over-the-top togs for casual, yet chic streetwear at the 2021 American Music Awards.
Sauntering into the ceremony in a minty green puffer jacket by Entire Studios, the lyricist gave new meaning to unfussy finery.
With celebrity stylist Storm Pablo as his guide, Bad Bunny paired the cropped piece with a white tank and sea foam pants.
He finished the ’fit with a pair of poofy, insulated shoes, in which he walked away with AMAs for “Favorite Male Latin Artist” and “Favorite Latin Album.”
No holding back
Going all business-in-the-front, party-in-the-back, the “I Like It” rapper stunned in custom Jacquemus at the 2023 Met Gala.
The white double-breasted suit jacket — featuring a peek-a-boo cutout in its posterior — gave anyone standing behind Bad Bunny an eyeful of skin. He accessorized with a long chain that boasted a shiny “J” emblem.
His tweed top was adorned with white flowers on each sleeve. The rosettes cascaded down onto the 26-foot taffeta train that trailed him as he walked the soirée’s steps with couturier Simon Porte Jacquemus.
Crème de la cream
Making monochromatic looks cool again, Bad Bunny abandoned his formerly splashy tastes for a homogenous cream-colored suit at the Dior Summer 2025 men’s show during Paris Fashion Week in June 2024.
His colorless outfit included a single-breasted blazer and oversized trousers. The Spanish-speaking supremo kept things muted with a beige knit tee and a simple gold chain.
With a large, leather tote bag in hand and rectangular shades on his face, the hotshot offered onlookers a hint of whimsy with a pair of green suede shoes on his feet.
Who says dressing understated is overrated?
Puerto Rican regalia
Bad Bunny wears his homeland pride on his sleeve — quite literally.
The glamour guy spent most of early 2025 promoting his Grammy-winning album, “DeBí TiRAR MáS FOToS,” wearing guayaberas in deference to his Caribbean roots.
Guayaberas, lightweight linen or cotton shirts made with four frontal pockets and several vertical pleats, have origins in the Philippines, Cuba, Mexico and Puerto Rico. For his traditional garb, the “DtMF” creator turned to Puerto Rican designer Yazmin “Yayi” Perez.
She churned out eight tops for the rapper, each customized with elements that celebrate both his album and Puerto Rican culture.
Too hat too handle
When it comes to marching to the beat of one’s own drum, hats off to Bad Bunny.
The fashion plate turned heads at Calvin Klein’s fall 2025 show, sporting a black suit from the designer’s collection along with his beloved baseball cap, reading, “Saint Barth West Indies” in black thread.
The hat — an accessory Bunny reportedly purchased from an old local shop while visiting the island — has appeared atop the luminary’s noggin on a number of posh occasions, including the “Saturday Night Live” 50th anniversary show, his Tiny Desk concert with NPR, and, of course, in vids for his 35.8 million TikTok followers.
He’s Prada his heritage
Looking fine and dandy at the 2025 Met Gala seemed almost effortless for Bad Bunny, who slayed the scene in a brown Prada suit and a custom Pava — a wide-brimmed straw hat that’s historically worn by Puerto Rican jíbaros (rural farmers).
He styled the appealing apparel with embellished gloves, a leather bowling bag, and sunglasses in celebration of the museum’s exhibition, “Superfine: Tailoring Black Style.”
While describing his dapper duds to Vogue, Bunny humbly said, “I hope that people think that I’m looking good.”
The luxe tux
Bad Bunny’s Album of the Year win is just as iconic as the Schiaparelli tuxedo he premiered at the Grammys on Feb. 1.
While the rapper’s album made history as the first Spanish-language anthology to ever receive AOTY accolades, his ensemble also shone as Schiaparelli’s first-ever custom haute couture menswear look.
The black velvet smoking jacket, designed by creative director Daniel Roseberry, featured a pinched waist and exaggerated shoulders, playing up Bunny’s love of feminine-meets- masculine silhouettes. The luxe look was made to perfection with a measuring tape motif that marked his lapels, and a corset-like lace detail that danced down his spine.
A white floral pin, a white pocket square, a black bow tie and Cartier jewelry dazzled as finishing touches.