Thanks for the info and links. These will be useful in finding a brimmed hat that works for me.
You can reply any way you want Booli. No need for apology. You are accepted here. Those are pertinent questions.
Yes, Charlie Chaplin wore a bowler or derby hat. A great starter bowler of good quality is Jaxon. They have a stiff wool bowler in black and in grey. I have the black one and it is nice.
Sinatra I believe wore more of a shorter brimmed hat. The more dressy fedoras have around a 2.5 inch brim while stingier brims can be more 1.5 to 2 inch. I like both, but it really depends on your theme when you dress. Each hat is distinct when tilted sideways or back more, or more traditional horizontal to the ground. And also snapping brim up or down.
You have to try all sorts of configurations along w different colors w clothing colors or complexion.
Some believe certain brimmed hats only look good on certain faces or certain body types but I personally don't believe it. I have all kinds and I'm a very wide jawed person.
Depending on the mood I'll tilt my hat a certain way
Depending on the clothing type or event or casual situation, I'll wear a certain brimmed hat
Depending on the clothes colors I'll wear a type of colored hat.
But snapping a brim I'll always keep snapped up, as it is more jazzy than a mid century American trad look snapped down brim.
Thanks for the kind words, as well as the detailed info. I have some research to do.
When I was younger, a baseball cap was always with me in summer, and a wool ski cap in winter, but since getting more bald, it seems all the hair on top got burned off by the furious brain activity...
(Grass does not grow on a busy street)
A few years ago I discovered a lady on Etsy that makes cotton beanie caps (pic below) out of the same material used in the Hanes 'beefy' t-shirts.
They are usually called 'cancer hats' and worn by folks undergoing chemo who have lost their hair. I dialogued with her a few times and she hand-made a few of these hats just for me. I now wear them year-round. I feel completely naked without the top of my head covered.
This is a sample of what they look like from her page:
and this is her shop on Esty:
https://www.etsy.com/shop/EnglishTraditions
Since that first order, I have gotten more of them, and several in each color to coordinate with whatever colors I am wearing.
It would be nice to find a Bowler or Fedora, either one with a shorter brim, that I could wear on occasion instead, since most folks think that I am wearing the beanie for religious purposes, but the beanie is more comfortable and so much better looking than a bandanna.
I used to wear a bandanna all the time in the summer to keep the sweat from running into my eyes, but for some reason I must have looked rather menacing with the bandanna because I almost always got dirty looks since folks must have made negative assumptions about someone that wears a bandanna
(which is not at all helped by the over-hyped news stories).