Does the black hat have any holiness attached to it? Is there any meaning behind the black hat? No and no.
The fedora was standard issue for Europeans and Americans, Jews and non-Jews up until about 50 years ago. It was a style of dress that was appropriate for its time. Why do we cling to it today?
We cling to it like we cling to kugel. The black hat evokes the shtetl. There is a nostalgia associated with the black hat. It is a social phenomena.
So what's wrong with that? Nothing if that is where it ended. But the black hat has come to mean more than that. It has become like the handshake of the Freemasons. It is an entry into the exclusive club of orthodox Judaism. Shouldn't the entry into the club have more meaning than kugel? Wouldn't we be better off if entry was shmiras hamitzvos?
There are other problems. There is the idea that Jews are like Amish folks. We don't move on, we don't welcome change or adapt in outsider's eyes. Worse, we have started to think that we don't embrace change or adapt. See the latest bans on internet or the fear of joining the work force or pursuing advanced degrees. Orthodox Jews are becoming an anachronism and the black hat is the banner of stagnant thinking.
How about this one? Sephardim now wear black hats. To me that is blatant discrimanation. Sephardim wore turbans as their non-Jewish mediterranean neighbors did. Why should their anachronsitic head gear not be accepted and they have to adopt European anachronistic head gear. It just seems narrow-minded and bigoted.
Fast forward 100 years. Orthodox Jewish men will look as silly in their black hats as many of THOSE HAT WEARERS describe chassidic men. Those crazies wear hats from 200 years ago. We are only wearing 60 year old hats! /sarcasm/ Do you see how silly this is?
On a slighty more humorous note, hats are also associated with the Mob 'look'. Is it a coincidence that so many Orthodox Jews have been in the news (and the prisons) for their Mobster like behavior?
Then there is the halacha. The Mishna Brura paskens that when praying, a man must wear a hat. Does this give the hat holy status? Does this mean the hat is a requirement for effective prayer? Or perhaps it would have been just blasphemous to show up to shul with no hat as it would have been for Woodrow Wilson to leave the White House with no hat on his head?
Think about it this way: Would you go to an important job interview wearing a black hat? Is a black hat a normal way of "dressing up" in our society? Of course not? So why should we go to shul or for those that wear their hats at the supermarkets, go to the supermarket in a black hat?
Just because some social phenomena was a certain way in Europe 200 years ago does not make it Jewish or more Holy.
As it stands now, the black hat is the symbol of the yeshivish Jew. If you don't wear one you are saying "I am not one of you". That is a pretty drastic statement that one implies by not wearing a hat. So if you mind being labeled that way you probably should still wear that hat.
Personally, I don't mind all that much. I can still be frum without my hat and I don't feel like a gangster when I go out of the house.
(Black) Hat tip to Rabbi Eliyahu Fink of the Venice Beach shul for his musings.
Now WHETHER this coMmon sense attitude would go down in fedorable Jerusalem remains to be seen.