This article examines the evolution of the appearance of British musician, Matty Healy, lead singer of contemporary band The 1975, in his performance as a hybrid man in style and fashion magazines. Hybrid masculinity is often used by young white men as a form of assimilating aspects from marginalized groups into performing their identities. This is to distance themselves from the narrow confines of hegemonic masculinity through transgression. Healy’s performances of gay and feminized hybrid masculinities have emerged through his clothing, from early national success as a typical ‘emo’ kid ‘dressed in black from head to toe’ to a fully groomed, suited and booted Englishman, cover star of GQ and in demand as a model. Prior to global fame, Healy’s style referenced rock stars of the past and he was admired for his simple black clothing, boyish emo good looks and curly hair; style blog IdleMan.com refers to him as a ‘gothic hipster’. Yet in concert with his stylist, Patricia Villirillo, Healy has begun to play on the more feminized aspects of emo fashion such as performing in women’s skirts and dresses, and arguably has produced a twenty-first-century emo aesthetic. Moreover, he also adopts the appearance of a powerful man in a suit or for performances as well as photoshoots. Healy might now be dressed in a suit or tie for performing, as easily as he might wear a skirt, as many men in music have before him. Wearing skirts as an act of transgression highlights the lack of diversity in men’s clothing in its mundanity, and despite advances in acceptance of dynamic masculine identities through performing gay identities, performing hybrid masculinities through femininity, is still highly problematic.