There are ladies at my church that choose to wear hats. They have many different hats and look great on them. I, however, am not a hat person.
Well done you, your avatar is fabulous. Hats went out of general use as we all got better off. Back when there was no central heating, even in public buildings, keeping the extremities warm, as in hats, socks and gloves, was key to staying warm.
Now we have warm cars, homes, shops and just about everywhere, you don't see hats so much. They are more of a fashion item and you are right, if you are not comfortable wearing one then you will never be a hat person.
My own hat wearing was born out of the liking for The Fedora hat, but like you, I cover my head to hide a scalp condition. In my case it's
psoriasis that I hide away. Psoriasis is a chronic (long-lasting) condition in which the immune system becomes overactive, causing skin cells to multiply too quickly. Patches of skin become scaly and inflamed, most often on the scalp. At it's worse, it can look like a serious case of dandruff.
Years ago, a rather astute doctor carefully asked me some personal questions. He coaxed out of me how I dealt with my mother's premature death, she was just 35. It was probably the cause of my skin condition. He explained what psychosomatic meant and guessed that the stress caused the affliction. But life is what it is and my Fedora Hats cover a stressful past.