Edward Lee Winslow was born near Tuscola, Illinois, only son of Nathan Winslow, a confederate veteran of the Civil War. He spent his boyhood and early manhood in Fairmont, Indiana, where he studied with artist/educator Olive Rush (1873-1966).
He moved to Indianapolis in 1902, becoming a sign writer and commercial artist. He worked for Fertig and Keevers and Company and operated a cooperative sign company. He maintained his own studio for 15 years.
After 1932, he devoted his time to painting. Working mostly in oil he recorded the Indianapolis scene and rural central Indiana. In reality, he was largely a self-taught artist.