In her essay, “Walter Sickert: A Conversation” (1934), Virginia Woolf asserted that the painter Sickert is “a great biographer” while his portraits are more efficient than biographies at conveying the personality of a person. Reading this essay along with other Woolf’s writings concerning biography, I would like to argue that Woolf’s experiments with the form of biography can be considered in conjunction with the changing ideas and forms of visual art of her time, which may help us understand Woolf and her idea of “new biography” in a broader perspective of her contemporary cultural environment. In “Mr Bennet and Mrs Brown” (1924), Woolf boldly claimed that “in and about December, 1910, human character changed,” implicitly referring to the famous exhibition, “Manet and the Post-Impressionists,” organized by Roger Fry. By this occasion Fry introduced the revolutionary idea of Post-Impressionism which was foreign to the British public at that time. Refusing the traditional realistic representation of the subject, the tenet of this new trend of fine art was to express the subjective and more personal impressions of the artist, emphasizing the effect of lights and colors. In the essay, Woolf argues that the changing concept of reality necessarily asks for new ways of expression in art, endorsing modernist writers’ experimentations of character-making including her own, against Arnold Bennet’s criticism. In fiction, according to her, what is at stake is how to convey the character. Woolf is prone to making scenes rather than telling stories. As she observes in “A Sketch of the Past” that her desire to make scenes out of her experience is what made her a writer, Woolf’s writing has a strong affinity towards visual art, such as pictures, photos, and even the cinema. It seems that there is an interesting parallelism between Woolf’s idea of fiction and that of biography in terms of people in them either fictional or factual. While she was struggling with the problem of how to make a character real, she was also grappling with that of how to transmit personality of a person in biography. In this paper I venture to review Woolf’s idea and practice concerning biography in terms of visual art of the time, particularly portraits painted by Walter Sickert. It seems that Woolf took more conservative attitude towards biography than fiction. While she tried to incorporate the more radical ideas of contemporary culture of visual art, such as Post-Impressionism and Cubism in her fiction, which I believe shares the avant-garde sensibility of Bloomsbury intellectuals and artists, in biographical writings she kept herself contented with more realistic representation of Sickert. It may be because unlike in fiction, in biography she accepted the idea of the biographer is not free to invent and has to stick to “facts.”