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.