I chose 1945-1950. Every car being produced was beautiful, Boogie Woogie music was king, animated cartoons were in there prime, streamline moderne or "art deco" was still going strong and the war was over. If I had to choose an exact date I'd say January 1st 1947.
$69.52 BIN on sale.
http://www.ebay.com/itm/Vintage-50s-DAYTONS-Wool-Charcoal-Hollywood-2-PC-Suit-31w-40R-Rockabilly-/290816995555?pt=Vintage_Men_s_Clothing&hash=item43b60b30e3
1950's Dobbs Westward. A little stained and moth eaten but it'll make a nice "knockabout" hat.
Found this envelope/playbill thing behind the sweatband.
That's definitely authentic '20s/'30s. 2 button cuffs were common in the '20s and '30s (I have a 1926 dated suit with 2 button cuffs), the material and cut of the suit, and don't forget the pants, all point towards pre-WWII.
Low BIN, and comes with 1942 newspaper ad for the company that made the coat.
http://www.ebay.com/itm/Vtg-1940s-UNION-MADE-Cunapac-Overcoat-46-R-coat-gangster-WWII-wool-alpaca-/200904005286?pt=Vintage_Men_s_Clothing&hash=item2ec6cfd6a6
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