The interdisciplinary project under discussion is suitable to be addressed to students of either primary or secondary education and it interweaves the art of painting with fairy tales. The aims of the project are: the deeper understanding of the complexity of human nature and the sensitization of students regarding gender roles and stereotypes. On the occasion of a visit at the Museum of Modern Greek Art of Rhodes and with the painting of D. Mytaras, named "Woman in the Mirror" as a pretext, we started a discussion which resulted in a focused project, through which students who participated in it, improved self-perception, promoted their communication competence, realized the existence of gender stereotypes, negotiated the dominant viewpoints and even adopted critical stances that challenged gender inequality. The mirror was the starting point from which the project was deployed. Woman in the mirror usually stands for female vainglory, coquetry and self- assumption. After exploring the symbolic charge of the mirror through a variety of artistic representations and fairy-tale narratives, both traditional and postmodern, where the woman in the mirror was the pivotal theme, the students expressed themselves uninhibitedly and voluntarily and in the end they produced visual and textual creations. Freed from the constraints of conventional teaching and of the performance anxiety, intrigued and engaged by both the process and the subject matter, the students responded positively during every phase, proving through their final works that they had reached a satisfactory level of self-consciousness and of understanding the factitious nature of gender roles, having adopted a more mature and objective--compared to their initial one--attitude towards gender stereotypes.