[beelzepug]

Are you talking about the flat caps like the old English and Irish wear?

[Rodamala]

The town I am in has a pretty large retired population... larger than "normal" I saw 2 elderly gents at 2 different times during the day with those black European fishing boat captain hats like the guy on the left in this picture:

For driving around town in a Buick of his choice though, I am thinking classic fedora hats of respectable men like Tom Landry or Bear Bryant wore.