Anna Alekseyevna Orlova-Chesmenskaya was the only daughter of Count Aleksey Grigoryevich Orlov, a landowner in the Rybinsk region. He was a military leader and statesman, a confidant of Empress Catherine II, and the younger brother of her favorite Grigory Grigoryevich Orlov.

Anna Orlova-Chesmenskaya inherited an enormous fortune from her father. At the age of seven, she was appointed a lady-in-waiting to the imperial court. She later received the Order of Saint Catherine for her services.

Over time, Anna Orlova-Chesmenskaya became a deeply religious person, even an ascetic, by secretly taking monastic vows, as her contemporaries believed. Archimandrite Photius had a significant influence on her. The portrait painted by Ivan Bazhenov is dated to February 1838, the year her spiritual father passed away “after taking on severe ascetic practices.”

Anna Orlova-Chesmenskaya was actively involved in charity and had a critical perspective on the institution of peasant serfdom. In 1833, she became one of the first members of the Russian nobility to allow her serfs to become “free plowmen” (a social category, also known as free farmers or free agriculturalists). This included peasants from the Chudinovskaya, Sretenskaya, and Nikolskaya volosts within the Rybinsk Uyezd. In exchange for payment or performance of specific duties, they were granted personal freedom, as well as a plot of land.

In this portrait, Orlova is depicted in the same attire as in the watercolor painting by Pyotr Fyodorovich Sokolov, completed seven years earlier and now housed in the Russian Museum. She has the same large red hat, blue-and-white dress with an intricate collar, and even the earring and string of large pearls around her neck. However, the two portraits convey different impressions: the watercolor shows a charming, youthful fashionable lady who looks at the viewer with a sweet smile, whereas Bazhenov’s version portrays a tense and indifferent countess, mainly occupying one corner of the canvas. Her hands are limply folded on the back of the chair, her head, although held high, seems to be tilting downwards under the weight of her hat with white feathers. Beneath the meticulously styled curls, her face looks rather old, with a distant expression and lips that refuse to form a smile.

The painting belongs to the genre of ceremonial portraiture. The color palette of the artwork is executed in the style of classicism and is characterized by a high degree of contrast, which contributes to a solemn atmosphere.