[1] She graduated from John Fitch High School, and trained as a teacher at Miner Normal College in Washington, D.C., completing her studies there in 1925, before earning a bachelor's degree at Howard University in 1928.

[3] In 1944, she completed doctoral studies at Teachers College, Columbia University, with a dissertation titled " A Program of Guidance and Recreation in the Day Care of Children of Working Mothers in Hartford, Connecticut".

[4][5] After college, Winston worked as a typist for a cousin in Miami, Florida, and taught typing classes at a night school there.

[10] In her seventies, she taught English at Calvin Coolidge High School in Washington, D.C.[11] Winston was a member of Alpha Kappa Alpha[10] and the National Council of Negro Women (NCNW), and national chair of the NCNW's Youth Conservation Department.

[14] In 1951 she was featured in a Nigerian newspaper report on eleven prominent Black women in the United States, along with Alice Allison Dunnigan, Freda DeKnight, Flemmie P. Kittrell, Sadie Tanner Mossell Alexander and Ella P.