This article draws upon theories of gender, nation and haunting in order to examine what we term the spectre of the boy in a dress within two international contexts, Sweden and Australia. These two contexts have been chosen because, on the surface, they appear to be very different and yet as our analysis will reveal there are striking similarities around gender conformity discourse and nation, although they play out differently. We illustrate how the notion of the boy in a dress is drawn upon as a problematic figure within these two different socio-political contexts, and argue that this figure represents a ‘tipping point’ between the tolerance and intolerance of gender diversity within public and educational spaces. Two key moments will be analysed. In Australia, the recent (2017) postal survey on Marriage Equality saw a campaign run from a conservative right group, the Coalition for Marriage, that included a television commercial featuring a concerned mother stating that, ‘School told my son he could wear a dress to school if he likes’. In Sweden, in 2016, the department store Åhléns chose an image of a child of African heritage and indeterminate gender to be the face of their annual Lucia marketing. This caused significant controversy and sparked a ‘Jag är Lucia’ (I am Lucia) campaign featuring notable Swedish celebrities dressed as Lucia, including footballer Zlatan Ibrahimović. These critical incidents act as illustration of how the power of cisgender normativity intersects with notions about the nation, within educational spaces and public consciousness.