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Juxtaposing the work of artists Jeff Koons and Michael Zavros, this article examines the link between the performance of heterosexual masculinity and menswear. Notable early work of Zavros includes black and white, hyper-realistic duplicates of men’s fashion. Yet, in Zavros’s work, masculinity becomes unbound and absurd with a series of illustrations by Zavros in which the torsos of models wearing Burberry and Gucci are combined with the lower halves of horses. Koons, well-known for his fashion collages and subsequent lawsuits from fashion photographers, places himself at the centre of his Made in Heaven series, in which he is depicted having sex with his ex-wife, former porn star La Ciccolina, in a variety of graphic positions. Zavros, in turn, re-imagines himself as a mannequin in his series Dad, and poses with his family in settings both banal and exotic. Zavros uses his family within his work often, including his children in paintings as well as video works. When performing masculinity in art depicting oneself, how does fashion, family and fame come into play? This article will examine not only how Zavros continues the legacy of an artist like Koons, but also how this transformation effects the self-performance of the male artist.