After her return to the United States in 1896, she studied briefly at the Pennsylvania Academy of the Fine Arts in Philadelphia, and then joined Howard Pyle's famous illustration class at Drexel Institute.

She developed a commitment to Quaker principles of pacifism, equality of the races and sexes, economic and social justice, and international government.

Oakley was raised in the Episcopal church but in 1903 became a devoted student of Christian Science after a significant healing of asthma while she was doing preparatory study for the first set of Harrisburg murals in Florence, Italy.

[3] In 1915, Oakley was awarded the Medal of Honor in the painting category at the 1915 Panama–Pacific International Exposition in San Francisco for her 1912 portrait of Philadelphia poet Florence Van Leer Earle Coates as "The Tragic Muse".

[8] Oakley and her friends, the artists Elizabeth Shippen Green and Jessie Willcox Smith, all former students of Pyle, were named the Red Rose Girls by him.

[9] Her home and studio at Yonkers, New York, where she resided intermittently between 1912 and 1915 is also listed on the National Register of Historic Places as the Plashbourne Estate.

As educational opportunities were made more available in the 19th century, women artists became part of professional enterprises, including founding their own art associations.

[16] Artists "played crucial roles in representing the New Woman, both by drawing images of the icon and exemplifying this emerging type through their own lives."

[20] Oakley painted a series of 43 murals in the Pennsylvania State Capitol Building in Harrisburg for the Governors Grand Reception Room, the Senate and the Supreme Court.

Oakley was originally commissioned in 1902 only for the murals in the Governor's Grand Reception Room, which she titled "The Founding of the State of Liberty Spiritual."

When Edwin Austin Abbey died in 1911, Violet Oakley was offered the job of creating the murals for the Senate and Supreme Court Chambers, a 16-year project.