Bad Bunny, the Puerto Rican singer, is set to headline the Super Bowl Halftime Show on February 11, 2026. His remarkable journey in the music industry has been paralleled by an equally dynamic evolution in fashion. From his early days in 2016 to his current status as a global icon, Bad Bunny’s style choices have sparked conversations, showcasing his fearless approach to menswear.
As fans anticipate his appearance at the Super Bowl, a look back at his most memorable outfits reveals both triumphs and missteps. His fashion journey encapsulates a narrative of bold experimentation, aligning with his personal mantra expressed in his song “Yo Visto Así,” where he asserts, “I wear what I want, I won’t change / If you don’t like it, you don’t have to look.”
Iconic Fashion Moments
One of Bad Bunny’s standout moments came at the 2026 Grammy Awards, where he made history by becoming the first artist to win Album of the Year for a foreign-language album. His custom Schiaparelli Haute Couture tuxedo, designed by Daniel Roseberry, featured an innovative lace-up back and a measuring tape motif on the lapel. Accompanied by diamond Cartier jewelry, this ensemble was a testament to his elevated style, as noted by stylist Storm Pablo, who described it as “the most elevated version” of the artist.
At the SNL50 Homecoming Concert in 2025, Bad Bunny’s burgundy suit and bright blue shirt drew inspiration from legendary salsa icons like Hector Lavoe. The look resonated with the vibrant energy of New York’s salsa scene in the 1970s, capturing the essence of his musical influences.
His appearance at the 2024 Met Gala was another highlight, where he wore a custom Maison Margiela Artisanal suit designed by John Galliano. This outfit, featuring a dramatic sculptural hat and unique stitching, solidified Bad Bunny’s status as a menswear innovator, earning critical acclaim for its theatricality.
During his headlining performance at Coachella in 2023, he embraced maximalism with a custom ERL patchwork puffer jacket and matching pants, embodying the vibrant atmosphere of the festival with an array of colors and patterns.
Fashion Flops and Lessons Learned
Despite his many successes, some of Bad Bunny’s early fashion choices left much to be desired. His floral Gucci suit at the 2017 Latin American Music Awards was widely criticized for being over the top. The suit, paired with excessive jewelry and a buzzcut, was a bold statement but lacked cohesion and sophistication.
In 2018, his shiny purple suit at the Billboard Latin Music Awards similarly fell flat. The ensemble, characterized by metallic fabrics and extravagant accessories, felt cluttered compared to his more refined later choices.
At the 2018 Latin Grammy Awards, his outfit choice reflected a chaotic blend of styles, featuring silver pleather pants and a zebra-print shirt. While it may have seemed adventurous, the look appeared disjointed when compared to his collaborators’ more classic styles.
His performance at Coachella in 2019 also missed the mark. Dressed in a loud Louis Vuitton ensemble festooned with logos, he struggled to find a balance between brand identity and personal style.
At the 2022 Met Gala, Bad Bunny’s bold Burberry outfit, with its dramatic puffed sleeves and skirt, received mixed reviews. While the look was conceptually rich, connecting to the event’s theme of “Gilded Glamor and White Tie,” it ultimately divided opinions, landing him on both best and worst dressed lists.
Bad Bunny’s fashion evolution reflects his growth as an artist and his willingness to take risks. As he prepares for the Super Bowl Halftime Show, audiences await not only his musical performance but also the potential for yet another memorable fashion statement. With his history of both hits and misses, Bad Bunny remains a compelling figure in the world of contemporary menswear.
