Kennedy wore a top hat to his inauguration. And I feel like any impression of Jackie features the pill box hat.

And Bond is British, what would he care about fashion trends on this side of the Atlantic?

The fact that there’s very little clearance for a proper hat inside of a car (as opposed to the higher ceiling in trains and buses) played a much larger role in killing the hat.

Along similar lines, there are chartered bus tours that you can sign up for to go to multiple destinations in a city farther afield.