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.
I've recently purchased a hat and I wore it the other night - a tall crowned, stingy brim, with a wide band (1" brim, 2" band). What was known as a "blue-beat hat" over here, but was just a standard 60's design in the States I suppose. Looks good with Ivy stuff if you're into that period (which I am) but difficult to wear without being really formal - unless you want that rude boy look! Will find a pic.