Winters was born in Chicago, Illinois and lived there until 1919 except for brief stays in Seattle and in Pasadena, where his grandparents lived. He attended the University of Chicago for four quarters in 1917–18, where he was a member of a literary circle that included Glenway Wescott, Elizabeth Madox Roberts and his future wife Janet Lewis. In the winter of 1918-19 he was diagnosed with tuberculosis and underwent treatment for two years in Santa Fe, New Mexico. During his recuperation he wrote and published some of his early poems. On his release from the sanitarium he taught in high schools in nearby mining towns. In 1923 Winters published one of his first critical essays, "Notes on the Mechanics of the Poetic Image," in the expatriate literary journal "Secession". That same year he enrolled at the University of Colorado, where he achieved his BA and MA degrees in 1925.