Chester Gillette was born in 1883 in Montana, and his youth was marked by numerous moves as his parents were members of the Salvation Army and relocated their family frequently. Chester and his siblings followed his parents on missions across Washington, Oregon, Wyoming, California, and Hawaii.
Gillette family circa 1900
As Chester matured, his parents were concerned about his education, which had been somewhat chaotic due to the constant traveling. His parents had given up their money and possessions when they joined the Army, and it was probably the intercession of the young mans well-to-do uncle, Noah Horace Gillette, that gave Chester the opportunity to attend Oberlin College's preparatory academy in Ohio.
Chester was a good student, but never found an enthusiasm for his studies, and he left the academy in 1903 after two years.
In the months following Oberlin, Chester
held various jobs, and was working in Chicago
as a railroad brakeman in 1905 when his Uncle Noah paid him a visit. Chester
followed his uncle back to Cortland, New York
, and began working at his uncles prosperous business, the Gillette Skirt Factory, in the spring of 1905.