I am follically challenged and have a huge melon as well. I enjoy wearing hats in all seasons, so I will give you a couple of my staples for winter. I wear a Lite Felt Fedora for the more formal days (try Shushans in New Orleans as they have a huge selection) and I really like the Kangol 504 wool (newsboy style) worn bill forward. If you want to transfer either of those styles to the warmer months, fedoras and newsboys come in different lightweight materials such as straw, cloth, and even paper (surprisingly durable).
My wife likes Stormy Kromer hats with the ear flaps that you can lower. Not my style, but she has converted our kids and several of our friends, both male and female. The Canadian Ski Team donned Kromers at the last winter Olympics. One last bit of advise is that black wool shows every piece of lint and stray hair. I don't know why, but it does. I would choose a strong gray, Loden green, or Brown before choosing black. Just my 2 cents.
My wife likes Stormy Kromer hats with the ear flaps that you can lower. Not my style, but she has converted our kids and several of our friends, both male and female. The Canadian Ski Team donned Kromers at the last winter Olympics. One last bit of advise is that black wool shows every piece of lint and stray hair. I don't know why, but it does. I would choose a strong gray, Loden green, or Brown before choosing black. Just my 2 cents.