See how Bad Bunny's style has evolved from his early days to the Super Bowl Halftime Show stage

If we go back in Bad Bunny style history, there are certain moments that stand out … and not in a good way. His floral Gucci suit at the 2017 Latin American Music Awards is one of them.

The then-up-and-coming artist wore a loud floral suit, paired with bedazzled, tinted sunglasses and excessive diamond jewelry, including grills and layered necklaces. The suit also had embroidered details on the lapel, which were accentuated by flower details, and diamond buttons.

While the singer — who had a buzzcut back then — might look almost unrecognizable in this look, it signaled his strong sense of style right at the beginning of his career.

Bad Bunny wore a shiny purple suit with metallic fabrics, embroidered details, and gems along the lapel edges. He wore it with an equally shiny metallic shirt underneath, a large diamond cross necklace, and lilac sunglasses.

While it was certainly a daring look, there was just too much going on, unlike the more pared-down, chic looks he would later wear.

While Bad Bunny's performance with Marc Anthony and Will Smith at the 19th annual Latin Grammy Awards brought energy to the night, fashion-wise, it was a bit confusing.

While Anthony stuck with his classic black-and-white suit, Smith opted for a sparkly black jacket and shirt for the stage. Bad Bunny, on the other hand, chose an outfit that was more of a reflection of the times' quickly fading trends, worn all at once.

He wore silver pleather pants, a zebra-print shirt, and a burgundy velvet bomber jacket, along with pink sunglasses, for the performance.

Onstage, the look felt out of place with his collaborators' style choices. It also probably started looking dated about 15 minutes after the performance ended.

The singer wore a loud Louis Vuitton matching outfit at his 2019 Coachella performance, pairing the oversized ensemble with visor-style lenses that covered most of his face.

The outfit was covered in pastel rainbow logos, leaving little room for mistaking the look for another designer's.

To accept the award for best urban music album at the Latin Grammys for his debut album "X 100Pre," Bad Bunny wore a look that combined multiple patterns and color palettes.

The singer wore a mismatching short-sleeve button-down shirt and plaid shorts with a zip-up turtle-neck-like collar, a black bucket hat, dark sunglasses, and Gucci knee pads.

The outfit matched the singer's 2018 album title "Yo Hago Lo Que Me Da La Gana," which translates to "I do whatever I want."

For his debut at the Grammy Awards, Bad Bunny went for an outfit that was playful without feeling gimmicky. While sticking to his characteristic playfulness, the look marked a shift toward a more sophisticated and polished image.

The singer wore an all-black Burberry look, which he paired with a hat resembling bunny ears and tinted sunglasses.

In contrast to his simple, monochromatic outfit, he carried a bright sunflower, which added to the look's playfulness and served as a nod to the more colorful, adventurous fashion choices he'd become known for.

Although simple, the sunflower detail was one of the most talked-about accessories of the night. "Bad Bunny's fully bloomed sunflower has managed to make my heart swell," wrote Vogue's Liana Satenstein.

For his 2022 Met Gala debut, Bad Bunny wore a bold Burberry ensemble designed by Riccardo Tisci. The look featured a camel-colored jacket with dramatic puffed sleeves, an eye-catching silhouette, and a matching skirt over a classic, more masculine-leaning, light-blue collared shirt and black tie.

He accessorized with a hair updo and small hand-held sunglasses.

The theme of the night was "Gilded Glamor and White Tie."

"I researched what was going on during the Gilded Age in my country, in Puerto Rico," the singer told Vogue. "We mixed the men's looks with women's."

It was an exciting, audacious look with a rich connection to the night's theme and Bad Bunny's roots, but it worked better conceptually than on the red carpet. It was a divisive choice, landing him on both "best dressed" and "worst dressed" lists for the night.

During his headlining set at Coachella in 2023, the singer wore a maximalist custom ERL patchwork puffer jacket and matching pants. The outfit was full of overly saturated, busy patterns that included florals, stripes, and plaid.

The eccentric and colorful look matched the show's stadium-level production and high-energy setlist as he performed songs from his 2022 summer album, "Un Verano Sin Ti."

At the 2023 Met Gala, Bad Bunny wore a custom all-white Jacquemus suit with a cutout back and a dangling "J" as a nod to the look's designer. It also featured a dramatic, 26-foot-long rosette cape.

The outfit was spot-on for the event, which honored the late Karl Lagerfeld, and broke away from traditional menswear choices, becoming one of the most talked-about looks of the night.

His third Met Gala appearance — and first serving as a co-chair for the event — was among the best and most acclaimed.

The singer wore a custom Maison Margiela Artisanal suit designed by John Galliano that stood out for its theatrical flair.

It included a navy suit with white stitching detail, a dark floral fabric bouquet, and a surreal sculptural hat that reflected the fashion house's avant-garde style. The outfit also included leather gloves, geometric sunglasses, and a horse-like pair of Margiela's signature Tabi shoes.

The look was commended as one of the night's best and cemented the singer's growing presence as a menswear icon.

Performing at the SNL50 Homecoming Concert in New York's Radio City Music Hall, Bad Bunny paid homage to the style of legendary salsa singers like Hector Lavoe and Willie Colón.

His burgundy suit and bright-blue shirt, paired with Ray-Ban tinted sunglasses and gold jewelry, gave the singer a look worthy of the New York salsa scene in the 1970s and 1980s.

The look was a nod to the many salsa influences in Bad Bunny's latest album, "Debí Tirar Más Fotos."

At the 2026 Grammy Awards, Bad Bunny didn't just make history as the first artist to win the album of the year award for an album sung in a foreign language, but he was also the first to wear a custom Schiaparelli Haute Couture menswear look on a red carpet.

To receive the big award, the singer wore a black-tie tuxedo designed by Daniel Roseberry. It featured a corset-like back lace-up detail, an exaggerated silhouette that's a signature of the fashion house, and Schiaparelli's measuring tape motif on the lapel.

The singer paired it with diamond Cartier jewelry.

His stylist, Storm Pablo, said the outfit was "the most elevated version" of the singer, per Vogue. "This is something really refreshing and new," Pablo added.

Bad Bunny's Halftime Show at the 2026 Super Bowl made headlines for its historic message, cultural significance, and celebrity cameos, but while some expected his fashion choice to make headlines on its own — with some even speculating he would wear a dress during the show — the actual look didn't outshine the performance.

The singer wore a custom Zara outfit that included an off-white collared shirt, matching wide-leg trousers, and an oversize football jersey.

The jersey showed his mother's last name, Ocasio, and the number 64 in honor of the singer's late uncle, who used to play football under that number, Complex reported.

While the singer's outfit stuck to his more recent style, characterized by monochromatic neutral colors and bold silhouettes, it looks wildly different from his early career days.