Orest Kiprensky gained true recognition with his magnificent portraits that convey the beauty of feeling and subtle inner world of images by constantly unfolding deeper and deeper qualities of the person portrayed.
The first portrait that gained him acknowledgment at an exhibition in Saint Petersburg in 1804 was Adam Shvalbe's Portrait. In 1805 the artist was awarded a big gold medal for his painting Dmitry Donskoy at the Kulikovo Field.
Contemporaries compared his works to the genres of lyrical poetry and poetic dedications to friends that were widespread in the time of Alexander Pushkin. Orest Kiprensky in many respects discovered new opportunities in painting. Each of his portraits has a new painting system, well matching light and shade, and various contrasts. Some of his well-known works are Self-Portrait, and portraits of A.R. Tomilov, I.V. Kusov, A.I.Korsakov, A.M. Golitsin, etc.
In 1816 Orest Kiprensky went to Italy, where his portraits were very highly estimated by the Italian public. He was ordered the Self Portrait in for the Uffitsi Gallery in Florence – the attention paid to great artists of the epoch. ainter secures the order. It was followed by Denis Davidov's portrait in 1819, The Girl with a Poppy Wreath and the most successful portrait of Alexander Pushkin in 1827. In 1812 Orest Kiprensky was awarded the title of the Academician of Painting. During the Patriotic War in 1813 he made lots of graphic portraits of the war veterans, such as E.I.Chaplitsa, A.R. Tomilov, and others. Some of Orest Kiprensky’s projects remained unfulfilled.