The Wedding of Maria de’Medici and Henry IV by Jacopo Chimenti da Empoli is a large oil painting commissioned especially for the wedding of Maria de’Medici and Henry IV, King of France by the Florentine court in 1600. The painting aims at commemorating the marriage alliance between the French royal family and the Medici, celebrating family honour and demonstrating a new form of group portrait created with outstanding painting skills. Thanks to the flourishing of research into the study of Renaissance clothing, it is understood that clothing is a key to understanding Renaissance culture and society. As such, the depiction of a sitter’s clothing in portraiture and its connotations has emerged as a new field of art historical studies. Nevertheless, current research on The Wedding of Maria de’Medici and Henry IV not only fails to consider it in the context of visual culture of marriage, but also underestimates the importance of sartorial message delivered by the depiction of dress. Thus, this article aims to discuss the political and cultural connotations of the portrait through a detailed study on the depiction of sitters’ clothing, especially that of the Spanish gown worn by Maria de’Medici. In doing so, the article provides an insight into the visual experience of early modern aristocrats and explores how the dress conveys subtle but vital, political and cultural connotations.