The purpose of this study is to analyze the representation of masculinity of Mikhail Tereshchenko as painted by Alexander Golovin at the beginning of the 20’th century, and to connect masculinity to the values of dandyism. An iconological analysis, in the style of Erwin Panofsky, and literary research resulted in various findings. Dandyism could partly be seen as a reaction against the normative masculinity, or hegemonic masculinity stated by R.W. Connell. Both Tereshchenko and Golovin were in their everyday life surrounded by highly regarded dandies and it is likely that they were influenced by the sprezzatura, esthetics and values of dandyism. The portrait reveals the wealth and status of Tereshchenko through the clothing and artefacts visible in the painting. These objects correspond with the importance of the ‘detail’ in dandyism. Golovin and Mir Iskusstva is a great example of how artists as a social group nourished dandyism in ways other than outer appearance.