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Analysis of a few recent publications on transgression and gender inversion in the Middle Ages shows a new historiographic trend to interpret the concept of gender as a spectrum with different gradations, as opposed to either the strictly binary model (masculine and feminine) or the one-sex model, wherein the woman is considered a “defective man”. Study of the historical constitution of genders in the tradition of physiognomy is followed by an analysis of the anatomical sexual ambiguities the hermaphrodite and the eunuch. From the end of antiquity, these cases were the subject of juridical considerations, which gradually removed them from the categories of monstra or portenta. Reflection on the concept of masculinity during the Middle Ages (chiefly in relation to the clergy) and a note on homosexuality show the usefulness of a cross analysis of the university quaestiones of philosophers of nature with those of medical doctors.