Riles enrolled in Arizona State Teachers College (NAU), and graduated in 1940 with a major in education and a minor in history. He was the first black student there and fought in WW2 as a pilot.

Wilson Riles served as a principal of Flagstaff's Dunbar School until1954.

He and others worked to desegregate Flagstaff public schools, and was successful, prior to the Supreme Court decision of Brown v. Board of Education in 1954. Due to his efforts, the Dunbar School was closed in 1954, when the students were sent to South Beaver and other local schools.

Riles joined the California State Department of Education as a Consultant in Certified Employment Practices, and was the Department's first African-American professional employee.

Riles was elected as the State Super intendent of Public Instruction of California. He was re-elected in 1974 and 1978. He was the first African American to be elected to an executive position in the California State government

Riles received an honorary master's degree from Northern Arizona University President Lawrence Walkup

The historic course case decision - Larry P. v. Riles - the Supreme Court rules that as a result of the overrepresentation of Black children receiving special education services, the state of California will no longer utilize IQ tests to determine placement.