This paper presents an art-historic contribution, examining the bonnet and the beret as characteristic forms of female and male headdresses and their manifold variations and oriental origins. Both types of head coverings are shaped by sociocultural attitudes and evolved in form. Embedded within the wider context of clothing they also, in turn, influence social norms and attitude. Examining their history and genesis also reveals and raises gender-specific perspectives and questions. The depiction and representation of the bonnet and beret during two defining periods in the visual arts, incorporating role-play and creativity, present a considerable knowledge transfer through media. First instances of gender-specific dress codes can be traced back to the Bible and therefore Paul’s rules for head covering for women in 1 Cor 11,2-16 is intensively debated. The following chapter will trace and illustrate the history of female and male head coverings on the example of various works of art. The strict rules outlined in 1 Corinthian 11 prescribing appropriate head coverings in ceremonial settings, which had a significant and lasting impact, have in time been transformed through the creative freedom afforded by the mundanity of fashion.