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 1923 Winters published one of his first critical essays, "Notes on the Mechanics of the Poetic Image,"[1][page needed] in the expatriate literary journal Secession.

His students included the poets Edgar Bowers, Turner Cassity, Thom Gunn, Donald Hall, Philip Levine, Jim McMichael, N. Scott Momaday, Robert Pinsky, John Matthias, Moore Moran, Roger Dickinson-Brown and Robert Hass, the critic Gerald Graff, and the theater director and writer Herbert Blau.

[4][page needed] Around 1930, he turned away from modernism and developed an Augustan style of writing, notable for its clarity of statement and its formality of rhyme and rhythm, with most of his poetry thereafter being in the accentual-syllabic form.

[3][page needed] Winters's critical style was comparable to that of F. R. Leavis, and in the same way he created a school of students (of mixed loyalty).

His affiliations and proposed canon, however, were quite different: Edith Wharton's The Age of Innocence above any one novel by Henry James, Robert Bridges above T. S. Eliot, Charles Churchill above Alexander Pope, Fulke Greville and George Gascoigne above Sidney and Spenser.