Jessie White (circa 1896-1975) was a teacher in the segregated Albemarle County schools when she commissioned this portrait from the Holsinger Studio. Her father, Samuel H. White, was also a teacher.
The man in uniform might be her future husband, Charles Alphonso Simpson (circa 1896-1962), of Philadelphia. Although the couple did not marry until 1938, Simpson was a close friend of White family by no later than the mid-1920s.
After their marriage, the Simpsons lived in Charlottesville, by which time Jessie was working as a private nurse, before moving to New Jersey, where she worked as a seamstress.