The majority of multilinguals immersed in different cultures report feeling different when switching languages. Albeit the influence of personality on self-perceptions has been explored, little attention has been paid to acculturation aspects. This inquiry is based on a mixed-method approach combining questionnaire and interview data. Participants are 468 Italian migrants living in English-speaking countries. Results propose that participants’ personality characteristics defined their sense of belonging to either the heritage or host cultural scenarios. Migrants reporting to feel different when employing the local language scored significantly lower on Emotional Stability and Social Initiative and were less attached to the host culture compared to those who reported feeling no change. More specifically, respondents’ Emotional Stability and attachment to host culture practices constrained their sense of feeling different when employing the local language.