The postage says November of 1960.The Lighter colored hat is a size 7 1/8, the dark one I cannot see a size and it seems like it might be a size smaller????
These are from an estate sale and I do not know a lot about them but I'd be happy to try and answer any questions.
These are used vintage hats that show a little age, the dark one seems a bit more used than the lighter one.
Thank you for looking!