Hi,
I can't see the label on the first one, and I can't really make the hat out in your photo. But it looks like late 40s to early 50s. As I said I cannot really see it too well. Can you repost the label photo?
The middle hat with the Louie Miller label looks 1930's. Mr. Miller was around a long long time, making hats back in the 1920's, and eventually opening up his own millinery school (I think after WWII) which also did mail order courses and sold hat making supplies. The school was still around in the 1960s, maybe into the 1970's.
The last hat, the black on is fabulous! I date to the early 1950's, circa 1951-1953. I am not familiar with the maker, but have seen the label before. It is a really great hat.