This article provides new perspectives in interpreting the sartorial codes present in Orientalist portraits of European subjects. Art historians have traditionally implicated these works in the European imperialist project of appropriating, manipulating, and gaining mastery over the Orient. More recently, as part of a wider effort to challenge conventional portrayals of colonial encounters in purely confrontational, monolithic terms, portraits of Europeans in exotic dress have been seen as visual proof that certain Europeans may have ‘crossed-over’ or ‘gone-native’. This article advances a third perspective. Analysing several portraits of Europeans with Indian connections during the seventeenth, eighteenth and nineteenth centuries, it demonstrates the importance of analysing portraiture as an act of public performance. It shows that, in many cases, the performance of both artist and sitter alike were not intended for the colonial population, but for the spectators of colonialism situated ‘back home’ in Europe. Applying this new analytical approach to such an important and extensive genre of sources has far reaching implications both within the field of art history as well as within the broader domains of colonial history and contemporary East–West cultural studies. The interpretation of Western portrayals of the Orient – both visual and literary, both historical and contemporary – as active participants in an imperialist ideology must not eclipse the other, potentially less-charged, varied, and complex motivations of their participants.