That is a very snappy and sporty hat! I see the military influence as you have noted. It looks to be made if a nice quality imported fur felt velour. Judging just from the photos, I would place it in the early half of the 1940s, although it could be mid to late 1930s also.
Definitely late 1930's, early 1940's. I first became aware of fashion silhouettes in the 1940's. I can see it worn with a black wool gabardine coat like this one in my inventory waiting until fall to go on consignment.
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