bob hairstyle and soft makeup.
Jay Te Winburn of Montclair, New Jersey was the photographer of the second picture, and perhaps the first. A little checking for him in the census finds him in Montclair, Essex County, New Jersey in 1920 and 1930, working as a photographer.
|1920 census for 563 Bloomfield avenue, Montclair, Essex County, New Jersey|
15 July 1940
via Google Books