Had Violet Oakley not become a muralist, she would have had a successful career as a portrait painter. With the exception of mural paintings, portraits comprise the largest genre in the corpus of her work. The exact number of her commissioned portrait paintings has not been determined, but the surviving studies number over one thousand. Oakley was a precocious artist with a facility for capturing an expressive likeness. Her portrait of her aunt Frances Elizabeth Oakley, circa 1895, which includes a partial self-portrait in a mirror, demonstrates her awareness of James Abbott McNeill Whistler’s use of reflections in paintings of women. At the Pennsylvania Academy of the Fine Arts (PAFA), Oakley studied with Cecilia Beaux, the most successful woman portraitist in the United States, an indication that Oakley was considering a career as a portrait painter in 1896.
Oakley was never without a sketchbook and she frequently sketched her companions during social events. Numerous informal sketches in pencil, ink, or pastel depict her housemates, Jessie Willcox Smith, Elizabeth Shippen Green, and Henrietta Cozens, at the Red Rose Inn in Villanova and later at Cogslea in West Mount Airy. Over several decades, Oakley produced many portraits of her life partner Edith Emerson, such as the dramatic Edith Emerson Lecturing on Greek Art (1935).
As Oakley’s fame as a muralist grew, she began to receive portrait commissions from friends and associates, some of which were recognized not only for her interpretations of the sitters, but also for their aesthetic qualities. Her portrait of poet Florence Earle Coates (1912) was awarded the Medal of Honor in Painting at the Panama-Pacific International Exposition in San Francisco in 1915. Her posthumous portraits of two children of George and Gertrude Woodward, Henry Howard Houston Woodward (1922) and Quita Woodward (1939), both garnered awards at PAFA. Leaders in the fine and performing arts, politics, and academia sat for Oakley, among them violinist Albert Spalding, coloratura soprano Amelita Galli-Curci, social reformer Jane Addams, Swarthmore College professor William I. Hull, and Sarah Lawrence College founders, Sarah and William Van Duzer Lawrence.
After completing her mural commission for the Pennsylvania Supreme Court Chamber in 1927, Oakley concentrated on portraits of international political leaders. To document the establishment of international government, she made portrait drawings of the delegates to the League of Nations, the United Nations, and Moral Re-Armament. These collections record Oakley’s appreciation of the diverse global community striving for world peace.