Hi,
I have not seen hats with this label. Penny was a popular comic strip in the 1940's to about the 1960's, and was one of my mom's favorites when she was a young working woman. I agree with Nicole, looks to be early 1950's. It is possibly late 1940's as that style was seen from late '40s to late '50s.
The feather looks like wild turkey or similar, not sure if it is original but it is a bit large in scale for the small sculpted hat.
Cute!
B