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Earle B. Winslow was born on February 21, 1884 in Northville, Michigan, and several years later his family moved to Grand Rapids. After graduating from Union High School in Grand Rapids, Winslow studied at the Art Institute of Chicago until 1906 when he served a two-year apprenticeship at the Cargills Newspaper Engraving Plant.
In 1909, Winslow married Zenna Pearl, the former model of his Grand Rapids art instructor Mathais J. Alten. He moved his family to Detroit in 1913 where he was employed by the Franklin Press Company, and he attended the Detroit School of Fine Arts.
By 1917, the Winslows had two children, Marshall Ladd and Zenna Mae, and the family moved to Chicago where he continued his studies at the Art Institute of Chicago. The family moved again the following year to New York City, where Winslow studied at the Art Students league with George Bellows and John Sloan. Beginning in 1919, summers were spent in Woodstock where his tutors were John Sloan, Andrew Dasburg, and George Bellows. Classmates in Bellows' classes included Peggy Bacon and Dorothy Varian.
In 1921, Winslow created the "Bingville Bugle" comic strip at the Invisible Ink Studios of Woodstock, New York. It was from this popular publication that singer Bing Crosby took his nickname. When the publication was discontinued in 1924, Winslow was employed at Art Services in New York City. In 1929, he established his own studio at 219 West 14th Street in New York City, and executed the Exide Battery Account for which he won an Art directors Award. He had a solo exhibition at the Macbeth Gallery in April of the same year.
He was a member of the Society of Illustrators, the Artists Guild, the Art Directors Club of New York, and the Salmagundi Club, and did illustrations for The Saturday Evening Post, Cosmopolitan, Women's Home Companion, Liberty, and Outdoor Life. In 1935, Winslow was honored by the Linweave Paper Company of Springfield, Massachusetts, when they named "Winslow Texture" watercolor paper after him.
During World War II, he was commissioned to do posters and instructional material for the U. S. Marines and the Forestry Service. He also painted 30-minute portraits at the Stage Door Canteen and Seamen's Institute.
In 1948, Winslow became an instructor at Pratt Institute, and at Visual Arts and Cartoon Schools. He gave up his New York City Studio and moved permanently to Woodstock, New York, in 1953.
Earle B. Winslow died on June 21, 1969 in Woodstock, New York.