In this paper I will critically reflect upon an intercultural experience connected with appearance, dress, and the different mutual perceptions of 'others' in public space in current Moscow and Vienna. I will construe this experience as fundamentally different attitudes towards informal behaviour, appearance and gender ambivalence. One of the main causes of this situation I have located in the 1960s, a period of anti-authoritarian subcultural upheaval in the Soviet Union as well as 'the West'. The very different social, economic and political contexts of their emergence and their further ('socialist' vs. capitalist) trajectories are, as I will argue, at the root of the perceptions and connotations of casual wear and behaviour in the public spaces of present-day Moscow and Vienna.(author´s abstract) / Series: WU Online Papers in International Business Communication / Series One: Intercultural Communication and Language Learning