Contemporary debates about breastfeeding are saturated with ideas about what constitutes ‘good’ and ‘bad’ mothering, ‘achieved’ or ‘failed’ femininity frequently derived from Christian representations of the Virgin Mother. In this article we trace deeply entrenched values about the maternal breast through the representation of the Madonna del Latte, specifically concentrating on breast ownership and the depiction of unattainable motherhood. The myth of maternal femininity is then explored in relation to contemporary visual discourses of the nursing mother in which the narrative of unattainable or failed maternal femininity is challenged. The performance work of Megan Marsh-McGlone and the phenomenon of sharing ‘brelfies’ on social media are read as indicative of a new relationship to the Mary myth in which mothers expose the cultural fear of achieved maternal femininity. Ultimately, we argue that what is required of mothers is that they are held in a process of becoming maternal and that representations that subvert this imperative signal a shift in the landscape of Marian iconography.