Here are some photos showing detail of the hat and tie.
I'm not entirely sure how old the boater is, definitely no later than the 1950's. I'm guessing it's '40s at the earliest due to the font of the Dobbs logo on the interior, but I need to due more research on company logo's through the years. The price and size tags seem pretty pre-war in my opinion. Any hat experts out there have a clue?
My recent music obsession is thanks to a fellow Golden Era fan and artist known as "Two Strip Technicolor". Check out his retro work on his tumblr page at http://twostriptechnicolor.tumblr.com/tagged/Illustration. Follow him now, and enter for a chance to win a brand new 1951 Dodge Wayfarer and Zeineth Porthole television set!....not really but it's worth a look at!
And here's the song, "Nola" (1940) by Vincent Lopez and his Suave Swing Orchestra. Love the alliteration!