 At the 1904 Saint Louis International Exposition, Oakley won the gold medal in illustration for her watercolors for "The Story of Vashti," and the silver medal in mural decoration for her murals at All Angels' Church.In 1905, she became the first woman to receive the Gold Medal of Honor from the Pennsylvania Academy of Fine Arts.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 Earle Coates as "The Tragic Muse".