I usually wear some type of head gear if I am outside. I always remove it when indoors (as all well-bred gentlemen do).
Here's a glengarry:

I rarely wear them anywhere but the games. I own 4 or 5.
Here is a balmoral. I have 4 or 5 of them, too.

I also have a bunch of other hats including regimental tams and other glengarrys and balmorals, but you get the picture.
I also have a couple of broad brimmed hats for sunny weather or rain, and I own a few berets, but I can't get myself to wear the berets yet. (Oh, but they look good on Panache!)
P.S. the bear is on the mantle behind me and is not part of the balmoral.
Jim Killman
Writer, Philosopher, Teacher of English and Math, Soldier of Fortune, Bon Vivant, Heart Transplant Recipient, Knight of St. Andrew (among other knighthoods)
Freedom is not free, but the US Marine Corps will pay most of your share.
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