This paper problematizes the feature of being barefoot that appears to be an idiosyncratic feature found in Rubens’s depictions of (milk)maids, mythical and biblical female figures. To appreciate oddities Rubens created, the paper starts with a discussion that enlarges on the merits that we may gain from contemplating allegories set against pleasant-looking landscapes. It then scrutinizes the heated debates over the validity of iconic signs, which enables us to recognize our application of certain laws and principles as the essential condition in carrying out semiotic cum hermeneutic inquiries. We, therefore, become empowered on the one hand to perceive oddities as manifestations of freedom and play and, on the other, to unify different approaches the painter adopted on the same horizons of judging. All in all, this paper argues for the urgency of our developing morally creative conditions in justifying and interpreting strange and deviant forms.