The oldest gender-bender on the list, rapper Kid Cudi, is highly adored by Gen Zers, despite starting his career when most were still in primary school. Through his music, social media accounts, and public appearances, the Cleveland-born actor and musician has spoken out about depression, suicidal urges, and drug use, encouraging youth to find help when in need.
During his performance on Saturday Night Live in April, Kid Cudi, born Scott Mescudi, honored Kurt Cobain — one of his musical influences and childhood heroes — by wearing a floral dress similar to the one Cobain wore in 1993. The dress, created by Kid Cudi in collaboration with late Virgil Abloh, was met with criticism but only inspired the rapper to wear a dress additional times, including during the CDFA Awards in November. The 37-year-old rapper wore a custom-made wedding dress by California-based fashion label ERL and was accompanied by the brand’s designer, Eli Russell Linnetz.
After the awards show, Kid Cudi took to Twitter and shared a message from his 11-year-old daughter, who supported his choice to wear a dress, noting that her dad looked “very pretty” in his dress. Kid Cudi remarked that as long as his daughter is supportive of him, he’s happy.
Kid Cudi has been vocal about his nonconforming choices, including wearing nail polish and eye shadow, most recently during an appearance on HBO’s The Shop: Uninterrupted.
“I don’t give a **** about what anyone thinks,” Kid Cudi said. “I want to be a disrupter; I want to **** **** up. And it’s cool because I’m also giving confidence to the kids and telling them to be themselves and do what they want to do.”
