This article analyses the relationships between top management functional background diversity, organizational ambidexterity and firm performance in small sized independent (i.e. not part of a group) fashion companies. Fashion companies by their very nature can be seen as paradigmatic examples of firms which need to be ambidextrous. This study contributes to the emerging dialogue on the relationships between top management characteristics, CEO’s role, ambidexterity and performance in two ways. Firstly, it sheds light on the moderating role played by the industrial environment on the relationships between top management demographic characteristics, organizational ambidexterity and firm performance. Secondly, it provides a SE-level discussion on the antecedents, consequences, and mediating role of organizational ambidexterity.