Oscar Wilde's life, writing and mind were full of apparent contradictions, and many critics have interpreted this as a sign of fundamental insincerity. These contradictions were the result of a very deep cleft in his mental state. Two currents of feelings and thoughts ran through his life and gave his work the typical feature - paradox. It is very likely that Wilde loved paradox because it suited the peculiar duality of his attitude towards the world. The cleft in Wilde's emotional and mental life is so clear, and its influence on his work so strong, that any examination of his writing which does not investigate is necessarily superficial. The main aim of this study is to enlighten the essential elements of Wilde's aesthetics, philosophy and social attitudes by using a dialectic method of examination of Wilde's works and embracing both sides of his varied nature.