On 31 May 2015, a self-identified mother, Mari Niinikoski published an open post on Facebook. It was about her son, Lenni, and how adults constantly ridiculed him in various social situations for cross-dressing and for his interest in girly stuff and the colour pink. This article asks why it is a problem that a little boy likes pink and wants to wear a dress? Why is liking ‘girly stuff’ considered detrimental for boys? What is at stake – especially when the history of men and fashion indicates that skirts, dresses and pink were long part of a masculine wardrobe? When did skirts, dresses and pink become feminised and signs of deviant sexuality? To answer these questions, the article will address the question of fashion and sexuality, the history of skirts and dresses, the changing meanings of the colour pink, the problem of heteronormative childhood, and, lastly, the problem of hegemonic masculinity.