This one is from the late '30s: it's called the "Grouse". It's made of a fuzzy, hairy, very slightly wiry felt that looks a lot like a wool/rabbit fur mix to me. Made for Bullocks Wilshire (once a very high-end department store in L.A.) by "Palco Hats, Inc." of S. Norwalk, Connecticut. (A Google search revealed that "Palco" is famous for only one thing: a landmark court case in the early '50s.)
Note the brim stitching in the 2nd photo (similar to the stitches on the bottoms of covert coats), and the unusual ribbon and bow in the 3rd photo. Also, note that it's a bit similar to several hats shown in 1930s Esquire illustrations (at bottom).