Bad Bunny has worn dresses and feminine clothing in a few different contexts, so the answer depends on which moment you mean.

Key moments when Bad Bunny wore a dress

  1. “Yo Perreo Sola” era (2020) – music video and promo images
    • In the video for “Yo Perreo Sola” , released in 2020, Bad Bunny appears in full drag-style looks, including multiple dresses, wigs, and heels as part of a feminist, pro–women’s-autonomy message.
 * These visuals are the most widely cited example when people say “Bad Bunny wore a dress.”
  1. Red carpet and fashion events with skirt/dress elements (2022–2023)
    • At the 2022 Met Gala , he wore a Burberry outfit that included a tailored top with a matching skirt over a shirt and tie , blurring lines between a suit and a dress-like silhouette.
 * In **2023** , his all‑white Jacquemus Met Gala look featured a dramatic long rosette cape and cutout suit; while technically a suit, it contributed to his reputation for mixing masculine and feminine fashion codes.
  1. Ongoing “dress/drag” discussion and rumors (2025–2026)
    • Ahead of the 2026 Super Bowl halftime show , there were viral rumors and forum debates that he would wear a dress onstage, framed by some as a political or culture‑war statement.
 * Later coverage and entertainment news segments said he **would not** wear a dress specifically for the Super Bowl performance, even though the speculation kept trending.

So, when did he wear a dress?

If you’re asking about the most iconic instance people reference online, it’s the “Yo Perreo Sola” video released in 2020 , where he appears dressed as a woman in several outfits including dresses and heels.

If you mean mainstream red‑carpet fashion, a big example is the 2022 Met Gala , where he wore a Burberry ensemble with a skirted element that many fans and outlets described as him “wearing a dress” or “going gender‑fluid” on the carpet.

Bottom note: Information gathered from public forums or data available on the internet and portrayed here.