Starting in October of 1927, West Milwaukee students were able to attend high school in their own community. Before this time, students wishing to further their education beyond the elementary level had to attend classes at West Allis or Bay View area high schools.

The new West Milwaukee High School was planned by the architectural firm of Martin Tullgren and Sons of Milwaukee, and included an Alhambresque façade, light colored brick, columns and a red tile roof. Most schools built in the 1920s were constructed in the classical or Tudor style, but West Milwaukee High School differed with its Mediterranean styling.

The school was first founded as a junior high. It became a full four year secondary school in 1928 and held its first commencement exercises there in 1929. To accommodate a growing student enrollment, an addition matching the style of the original building was completed in 1937 according to designs by Associate Architects (Herbert L. Edling and Henry P. Plunkett). A new cafeteria, gymnasium and more classrooms were added in 1953 to the north of the original structure. In 1976, another major remodeling project was undertaken to upgrade the facilities. Among the more famous graduates of West Milwaukee High School was Walter Liberace, pianist and entertainer, from the class of 1937.