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Like many things, I believe it comes down to a simple matter of personal preference.
My father was born in 1913 and certainly lived in an era when the wearing of hats was commonplace. By the time I came along in 1961 my father held what would be called a "blue collar" job. Although I have seen a few photos from dad's younger days in which he was wearing one fedora or another (dad was truly a sharp dresser when the occasion called for it), in most of the older photos he is hatless, and I don't recall ever seeing him wear a hat while I was around.
My father-in-law was also born in 1913, and also held "blue collar" jobs. Unlike my father, he enjoyed wearing hats. My wife has told me that when she was younger her father wouldn't consider leaving the house without a hat much of the time. By the time we started dating in 1980 her father was wearing mostly more "informal" baseball caps, but more often than not would wear one whenever he left the house.
My father was born in 1913 and certainly lived in an era when the wearing of hats was commonplace. By the time I came along in 1961 my father held what would be called a "blue collar" job. Although I have seen a few photos from dad's younger days in which he was wearing one fedora or another (dad was truly a sharp dresser when the occasion called for it), in most of the older photos he is hatless, and I don't recall ever seeing him wear a hat while I was around.
My father-in-law was also born in 1913, and also held "blue collar" jobs. Unlike my father, he enjoyed wearing hats. My wife has told me that when she was younger her father wouldn't consider leaving the house without a hat much of the time. By the time we started dating in 1980 her father was wearing mostly more "informal" baseball caps, but more often than not would wear one whenever he left the house.
Thank you, Mayserwegener. 
