Frank Sinatra--probably from the time of his first great success with the Tommy Dorsey Orchestra in the early 1940s. Pretty sure he's wearing one of the then new-to-the-market Stetson Stratoliners and you can even catch a glimpse of the Stratoliner pin just over the brim.
I love that hat—you’re right it looks just like the hats you see in all those WPA photo from the 1930s of farmers and factory workers. I’ve been looking for one like that for years! ;)
David
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