I use the
Micheals/Jackson Rule, myself:
Brett Micheals - Wears hats/bandanas wrong. He does it to hide or disguise the fact that he is bald/ing. You NEVER see a pic of him without a hat or bandana on, EVER! and he's always got that whispy bleached thing hanging off the back of his hat/bandana. The point is, he is CLEARLY trying to hide something and that's wearing a hat for the wrong reasons.
Samual L. Jackson - Shaves or buzzes his head most of the time and frequently wears a Kangol in public. However, we regularly see him in movies with varying degrees of hair and hairloss. We know he's losing his hair and he makes no effort hide it. He wears hats a part of his personal style. He's doing it right.
The point is, when you look at Micheals you get the feeling he's hiding something, covering up. It's like Shatner's toupee. He's not fooling anybody. With Jackson, you don't get that feeling of "he's hiding something". And, consequently, if a pic of Brett Micheals hat/bandana-less surfaced tomorrow, it'd be all over the internet and tabloids and he'd be a laughing stock,
BECAUSE of the lengths he's gone to to cover it up and the sense of shame that goes along with it.
You can only be shamed by what you are ashamed of. I'm almost 40 (so, not exactly young anymore) and I was raised by my great-grandparents who were raised in the 20's & 30's. I was taught that a man should ALWAYS wear a hat outside the house, but to ALWAYS take it off indoors or when talking to a lady.
My Granddad (an Irish Immigrant) used to complain that John F. Kennedy murdered hats for men by being the first president EVER to NOT wear one to his inauguration in '61. He swore that after that young men stopped wearing them and they just sort of went away. I think he may have been right! If you look at movies and TV from the 50's ALL the men have hats!
Sorry, got sidetracked...
I live in Portland, OR. and I have a cotton flat cap, a felt pork pie, a wicker fedora and (most recently) a Carhartt Irvine Cap that all get pretty regular rotation in my wardrobe. I pretty much NEVER leave the house without a hat, because it's a part of my style.
We lose a lot of heat from the top of our heads, so a hat in Winter makes a lot of sense. In the Summer, too much Sun exposure is dangerous, so a hat in Summer makes sense.
Do what is both comfortable and honest to YOU and don't worry about what anyone thinks. Confidence comes from comfort. Be comfortable in your skin and confidence will follow.
And welcome aboard