Every street scene photo from the 1940's and 50's shows men wearing fedoras and other brimmed hats. Why did they stop?
Men in the northeast don't wear brimmed hats because they are always in automobiles and with headrests and high backed seats there's no room for brims. Baseball hats, however, do work. Those that do wear brimmed hats are often cowboys, or cowboy imitators, or outdoors people from Maine or wish to appear to be any of the former.
Truth is, as a dedicated dog walker, rain or shine, I've come to admire how well my fedoras keep off the sun and guide the rain and snow safely beyond my collar. The fedoras make sense. From time to time I've heard the fedoras referred to as "old man hats". When it comes to being an old man, I'm the genuine article. There's no sense trying to look like something I'm not.
When I was in a boatman's local of the Longshoreman's union I was already a Socialist sympathizer, if not actually a member. I sometimes wore a white cap, something like a canvas version of the Irish style wool tweed caps with small front peak and panel sewed top, that (mostly in my imagination) identified me as a Harry Bridges man, a lefty union radical. Though of course, by then (70's and 80's) almost no one in the east coast ILA knew who the hell Harry Bridges was. Some out west did and still do.
In a New York City strike in 1988 I was fired along with the other tug boat captains that would not cross the picket lines. In that sense, in my scheme of things, I legitimized my little white hat and stood comfortably with a couple of others who treasured their knowledge of labor history, Harry Bridges, and the clear eyed ideals of solidarity with other workers in the face of the inevitable greed, corruption and exploitation.