Swann Hats were made by Swann-Abrams. The company was founded in the 1850s and lasted into the second half of the 20th Century. There is quite a bit of information on them, when I have some time I will dig some of it up. It looks 1940s to me, particularly with the lack of a plastic tip liner...
https://www.nps.gov/parkhistory/online_books/npswapa/extContent/wapa/coast_guard/cg1.htm
Joe and @StoryPNW the Gay Cavalier ended @ 1940
https://www.thefedoralounge.com/threads/the-dobbs-diner.18579/page-106#post-2727970
and was replaced with the Gay Prince in 1941...
Joe,
Somewhere in the Lounge I posted GP ads chronologically from the first year. I'll see if I can find them and post the link. But I think they were an off-shoot of the 1930s Dobbs Gay Cavalier
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