Looking back at the Boom Years, we can find lots of photographs and illustrations of men going about their business.  Just traditional American clothing for them during the Eisenhower period and slightly beyond (and before, naturally).  JFK was praised by 'Esquire' for maintaining the tradition. 

How do you feel about headgear?  I only own one hat, one of those Stetson caps from John's, and my wife and daughters chortle each time I wear it.  Looking in the mirror, I remind myself of Douglas Hogg; which is displeasing. 

At the price it was, I wouldn't want the wind to blow it off.  Bad enough keeping a scarf anchored.