Irvine was born near Byron, Illinois (Rockvale Township, Ogle County), where his family owned farmland along the banks of the Rock River. Great-grandfather Alexander Irvine was one of the early settlers of the region, and grandfather Joseph W. Irvine was a prominent Rockford businessman. Wilson Henry Irvine graduated from Rockford Central High School in 1888, and moved to Chicago the next year. He worked at the Chicago Portrait Company, and took evening classes at the School of the Art Institute of Chicago. His passion for painting landscapes resulted in frequent trips to New England. Irvine was one of the first directors of the Chicago Artists’ Guild and the Chicago Artists Society; chairman of Chicago Commission for the Encouragement of Local Art; and one of the seven Painter Friends, alongside fellow landscape artist Guy C. Wiggins. Although he and his wife moved to Connecticut in 1918—where he was a member of the Old Lyme Artist Colony—he maintained his connections in Chicago and friendships in Rockford throughout his lifetime.