This paper intends to examine Oscar Wilde’s literary strategy – his manipulation of the contemporary theatrical conventions – along with his deployment of dandyism and his cultural background of the Anglo-Irish which contributes to his ambiguous attitude toward self-identity. In Wilde’s society comedies, the seemingly conventional elements that appeal to the audiences’ taste are ironically the subversive ideas in disguise. Through the perusal of the playwright’s dramatic works, we would discover a “political” Wilde with trenchant criticism toward society and an unbounded vision toward his self-creation.