I'd say the same.  I'm retired Air Force so...  But I wear a Stormy Kromer in the winter, an Irish Tweed in the Spring and Fall and a HB Bucket Hat or USAF Baseball Cap in the summer.  Sunburn on bald head, BAD.

About the same for me.
Never wore hats before being sly, and don't wear hats now (generous now with sunscreen though).
I do love the feel of cool wind and rain on the head now.

Well, since 22 hours ago I had hair, I couldn't tell ya. BUt I LOVE hats. I have a ton of ball caps - and each of them are stretch fit or fitted, I don't like ball caps with adjustable straps/velcro/snaps. Kinda glad about that now, I can wear one backwards and wont' have a bald window. I also have a few great hats called AZ shady hats. www.azshadyhats.com which are made in Wikenberg, AZ about 30 miles from me. I LOVE that company and their hats. their mottos is if the hat wears out before your head does, we will replace the hat. they are 98% UV protective and give a portion of their sales to skin cancer charities. (I DONT WORK FOR THEM) but love them. I have a mesh had to wear in the pool and a nice one for nights out. I imagine I will be wearing a lot more now. They do fit a little looser but I have replaceable sweat bands that can size it down 1/4 - 1/2. If you like hats, check them out. tell them Gimpy sent ya and they might give you a discount.

Less sine I became sly

As with many others, I use a knitted watch cap on really cold, windy days in winter. I don't even own a ball cap so, apart from selected moments in winter, I'm shiny and proud year round. After 15 years, it would seem odd to me to cover it.

Bumping an old thread.

...I wanna start wearing trilby hats, but I'm not confident enough to pull it off.

I've always loved hats, but I naturally have thick wavy hair (I'm recently bald by choice). I used to wear ball caps while doing physical labor to shade the sun and absorb the sweat.  But otherwise, I always wanted to wear something like a trilby or short-brim fedora.  The problem was the messed up hair as a result of wearing a hat.  Now that I'm "sly", I'm looking forward to buying one of these (pic below).  I think the bald look with a hat like this is cool.  Of course I would take it off when I enter a building.


Besides, Bruce Willis pulls it off okay:


And what about The Observer?:

<Sorry to resurrect an old thread but I saw no reason to start this over from scratch.>


Well I don't collect Fedoras just to leave them sitting around the house.  I've always been a hat guy and because of it even before my hairline started receding people were assuming that I was going bald, I realized that I was starting to have an issue when I was becoming reluctant to take my hat off for any reason. At least now it's clearly just for style as people can see that I have nothing to actually hide.

Funny thing is that when I still had hair I'd have to often hold my hat on when it got really windy, now I've found that the slightest stubble on my scalp grabs the inside of the hat like velcro and keeps it from flying off.