In Jacobus de Voragine’s Legenda aurea, five chapters are dedicated to saints that might be described as trans: Marina-Marinus, Margaret-Pelagius, Pelagia-Pelagius, Theodora-Theodorus, Eugenia-Eugenius (in the life of Prothus and Iacinthus). Natalia, Adrianus’s wife also passed as a man during Adrian’s martyrdom. The place of gender transition in the text is important, and the exempla from the Golden Legend were, as Giovanni Paolo Maggioni showed, an important resource material for preaching used in the Sermones ad sanctos and in the Sermones Quadragesimales. Nevertheless, female saints described as fortis are prefered to trans saints in the Sermones. In the Chronica Ianuensis wifes are described as mollis and there is one trans character, a pope, with a tragic end. The argument of this paper is to understand how the important focus on gender issues in the hagiographic compilation by Jacobus could be used in Sermones performed ad statum and how the ideas on gender formulated in the Legenda are transcribed in his writtings according to the audience, whether clerical or laic, attenuating the radicality of the masculinisation of saints, to adapt it to everyday practices. This paper deals with queer and trans theory to understand better the place of gender issues in preaching practices.