On August 29, 2023, the Municipal Authority of Milan (Italy) issued official guidelines promoting the use of gender-equal language in administrative communication. These measures aim not only to introduce new prescriptive linguistic norms but also to reshape the social representation of women by eliminating stereotypes considered incompatible with contemporary society. While acknowledging that the use of the feminine definite article la (the) before women’s surnames is common and acceptable in spoken Italian, the guidelines explicitly discourage its use in written language, arguing that an equivalent practice does not apply to men and that inclusive language should treat both genders identically. Adopting a qualitative case study methodology, this research examines a corpus of Italian press articles to determine whether this language policy has influenced journalistic practices regarding the use of the feminine definite article preceding women’s surnames. The findings reveal that la continues to be widely employed by Italian journalists, as it fulfills essential linguistic functions related to semantic clarity, gender distinction, phonetic balance, and grammatical accuracy. Its use does not convey discrimination or negative evaluation; rather, it linguistically marks female identity and differentiates women from their male counterparts in a transparent and structured manner. The study further contends that this regulatory intervention conflicts with the principle that language evolves organically as a result of usage, rather than being shaped by top-down institutional regulation. From this perspective, the guidelines reflect the ideological orientation of the progressive left-wing political forces currently governing the city of Milan, alongside the influence of transfeminist advocacy groups engaged in shaping contemporary language policies.