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Often revered as one of pop culture’s most erotic and sexually charged beings, Prince’s influence within fashion and gender expression is now being fully realized academically. Many fans have long linked their admiration to the Purple One with their own personal sexual awakenings, citing the musician’s overt displays of sexual liberation as being key within their own development. Although Prince never self-identified as queer, his fearless expression of self through fashion, performance and lyrics continued to defy traditional hegemonic masculinities throughout his career spanning across four decades. This article will discuss Prince’s varying disruptions of masculinities through his career. It must be noted that this study is not an expansive critique; rather, this article will focus upon three pivotal sartorial moments within Prince’s career that have played a defining part of his legacy as one of popular culture’s most revered and celebrated gender non-conforming stars. All three outfits represent a defining moment within Prince’s career from his emergence into pop stardom, mainstream success and the comeback following an arduous relationship with his record company. Through examining the musician’s wardrobe, this article will underpin the many ways in which Prince slashed gender assumptions through clothing and paved the way for many performers within the queer community after him.