Neither one of my children liked wearing hats as babies.
They made me "that mom" that was approached my complete strangers inquiring why my children weren't wearing hats. "They'll catch cold ya know. blah blah blah. other things that aren't my business" (I'd like to announce neither of my children have ever had a cold or ear infection or strep throat or flu or other lack-of-hat related illness. thank you very much)
I was/AM much more concerned about them wearing hats in the summer to keep the sun out of their eyes and just give them an extra added layer of protection against the sun.
I wish bald headed SON would wear a hat outside. Even covered in spf 50 from the tips of his ears to the tips of his toes, I would about sun exposure.
We practice in the house. And by that I mean, I give him hats to play with. I wear hats. Daughter wears hats (sometimes). I make up silly songs about how fun and cool hats are. He's coming around, but still not in love with the idea.
"Sure, Fine. I'll let you put a hat on me. For just a second."