Feraud said:Look for films where there are real working men characters.
I can recall a James Cagney picture where he wears a cap with a double breasted suit. Could it be The Roaring 20s?
See films like Tomorrow, The Grapes of Wrath, Of Mice and Men, etc. etc.
The central protagonist in The Informer, John Ford's early 30s film about an IRA informer, wears a newsboy, as do other characters in the movie. Victor McLaglen plays that character, Gypo Nolan, who probably has a newsboy in every scene. The film's is a newsboy tour de force, with a lot of characters wearing them, although the leader of the IRA unit is depicted wearing a Fedora, suit and trench coat (disclaimer, I'm mentioning this movie as a movie, not as a political endorsement or anything).
Ford's second Irish film, The Quiet Man, is also a newsboy tour de force. Both films are set, I think, in the 1920s, but the first film was filmed in 1935, so it wasn't really recalling an earlier era. I understand this question to relate to contemporary depictions of newsboys, say pre 1950 or so?