Born at Bergen Heights, New Jersey, into an artistic dynasty, Violet once remarked that her own interest in art was "hereditary and chronic" and maintained that she was born with a paintbrush in her mouth instead of a silver spoon. Both of her grandfathers were artists, and two of her aunts were painters. Her father, Arthur Oakley, was an amateur painter, and her mother, Cornelia Swain Oakley, was a portrait and genre painter, who established a studio in San Francisco before her marriage.
Violet grew up in Bergen Heights, New Jersey. Although her mother had cast aside her professional ambitions when she married, she encouraged Violet in art, and the girl spent many hours drawing. Although Violet's early drawings were cheerful and unconstrained, her childhood was not entirely carefree. She suffered from asthma and extreme shyness.
When her older sister, Hester, enrolled at Vassar College, Violet hoped to follow her. However, her parents were worried about her asthma and would not permit it. Instead of going off to school, she remained at home studiously copying the Old Master engravings that both of her grandfathers had collected on numerous trips to Europe.
In 1894, when she was twenty years old her parents finally permitted her to begin her formal art education, allowing her to accompany her father on the morning train to New York City to attend classes at the Art Student's League. There Violet studied with Irving R. Wiles and Carroll Beckwith until 1895, when her father's declining health prompted the family to take an extended vacation in Europe.
The family settled for a time in Paris, where Violet enrolled in the all female Académie Montparnasse and studied with Edmond Aman-Jean and Raphael Nevin. When Arthur Oakley's health failed to improve, the family returned home.
As she travelled and studied in America and Europe, she exhuberantly painted portraits and landscapes in a spontaneous, impressionistic style. The result was a body of work of jewel-like brilliance. In 1896 her father's illness forced Violet to concentrate on illustration. And the technique she developed as an illustrator grew into the mural style that made her famous.
In Philadelphia she rented a studio with her sister Hester, who enrolled in Howard Pyle's class at the Drexel institute. Violet signed up for two courses at the Pennsylvania Academy. After one term, Hester convinced her sister to switch to Drexel. Violet submitted a portfolio and was accepted. When she walked into Pyle's class in the winter of 1897, she noticed Jessie Willcox Smith immediately and was intimidated by her skill and confidence. "Still a little afraid of you - as that first day in Howard Pyle's class!" she wrote to her friend 33 years later.
Upon the death of Edwin Austin Abbey in 1911, she took over his commission to paint murals in the Pennsylvania State Capitol Building for the Governor's office, Senate Chamber and Supreme Court Building. Completed in her Cogslea studio, they became her life's work are among the largest in existence.
Not only was Violet Oakley a talented artist, she was also a social activist involved in the women's suffrage movement, and totally devoted to the ideals of international government and world peace. When the United States refused to join the League of Nations in 1927, Oakley went to Geneva herself as a self-appointed ambassador.
Violet was one of three female Pennsylvania artists in the Philadelphia area during the Golden Age of Illustration known as the Red Rose Girls, along with Elizabeth Shippen Green, (1871-1954) and Jesse Wilcox Smith, (1863-1935). Henrietta Cozens (ca. 1859-1940) kept the household running smoothly, supervising the more mundane tasks a housekeeper might well have undertaken.
The four women chose a common surname, dubbing themselves the 'Cogs' family (Cozen, Oakley, Green, Smith). Their arrangement was best described as a Boston marriage - a relationship shaped by deep friendship, though most likely tinged with romantic/sexual overtones. While Jessie and Henrietta eventually became an undeniable couple, evidence regarding the other women's inclinations was scantier and non-definitive.
Whether the women were sexual or not is unimportant. They were lesbians in the sense that they were two couples bound by love and when one married a (possibly gay) man, the scorned woman grieved, then found another woman to love and share a life with. A friend of the women, in later years said: "What does it matter if they were orgasmic? The point is they loved each other".
Violet Oakley passed away in Philadelphia.