I routinely wear a bucket hat with a bunch of buttons pinned to it, whenever I’m not wearing a bicycle helmet. I don’t think it’ll ever be “in”, but it suits me.
I occassionally wear a black cowboy hat, a nice Stetson I picked up in Texas. Yeah, that fits, a big Filipino-Russian guy in a cowboy hat. But it works for me.
Working outside on a sunny or rainy day, I’ll wear my USMC boonie hat (or, “cover” in USMC-speak). Driving around on a sunny day in the convertible, it’s usually the boonie hat again. Sometimes it’s the Stetson.
That’s when I’m not wearing my SF Giants baseball cap, which is most of the time but I realize the OP isn’t asking about that.
On occasion, I wear my barmah.
I have worn fedoras for years.
Last year my wife and I were in the city to take care of visa issues and I decided to finally find a proper top-quality hat.
I stepped into J. J. Hat Center on 5th avenue, an old store that looks like it hasn’t changed in a hundred years, and I walked out with a beaver fur felt fedora, several hundred dollars lighter.
It was worth it. I love wearing my new hat in winter, and it is one of the things I look forward to as the weather cools down.
ETA: for Ludovic, the answer is to look for a real hat store in your nearest big city. There is nothing like trying on dozens of perfectly fitting hats while a professional tells you about each one and makes recommendations.
Since I was a teen. Tennessee law requires boys to wear cowboy hats beginning at 14 years of age. Naturally, these must be adorned with feather hat bands, and the gaudier, the better.
I graduated to fedoras at age 20 or so, but still have a couple of Stetsons on hand. A nice straw panama for the summer, a boonie if fishing or boating.
My wife tries to buy them for me occasionally, but it’s like me buying her a purse. It just doesn’t work that way.
I have my late father’s sheared beaver Russian Ushanka that is awesome. I can’t throw it away, and I can’t bring myself to wear it. It just sits with the others, sending out memories whenever I open my closet.
I’m not sure what it’s called, but it’s straw and wide-brimmed. I only wear it during the summer, and only when the sun is shining. And I look gooooood in it.
I wear gardener type hats when I’m going to be in the sunshine for a while. Having said that. . .
No love for Homburgs???
Never wore a hat of any kind until I was in my mid-40s; hated wearing caps even while playing baseball.
Now: Large-brim fedoras (2), dress fedora (1), medium-brim panamas (2, 1 600-weave dress and one everyday summer hat), driver’s caps (2, 1 Jacaru leather and 1 Jaxon corduroy). I still have a helluva lot of hair and I wear hats to keep it tidy as much as for dress reasons. (Then there’s the skier’s cap and motorcycle balaclava I wear while driving the roadster, but those are functional; driving with your face wrapped in hair is A Bad Idea.)
And I got out my signed Giants hat for a few days early this month. Some might remember they won… oh, never mind. No one follows baseball any more.
I have half a dozen hats. Fedoras, Bowlers and at Christmas I wear a tophat to parties.
As a Canadian tuque wearer, I’m slightly offended and puzzled that you don’t think ‘stocking caps’ are real hats!
I might get one - I think it’s about the only option left - and as long as I don’t start sporting a waxed moustache, I shouldn’t be under suspicion of trying to emulate Poirot.
Heh, asking if any guys on the Dope wear hats is like asking if anybody here has an opinion on Kirk vs Picard.
Who are they? 
My 14 yo son, Ledzepkid (doesn’t post much), has worn a fedora nearly every day for almost 2 years now. He has the one in the picture which is black material, and one that is grey wool. It suits him. Both his hats were fairly inexpensive, but if he keeps up with the style he may end up getting a quality hat for his birthday.
I don’t do [del]prole[/del] baseball caps but I do have one of those flat-top cadettype caps. I also have a derby, an Irish Walking Hat, and an Irish flat cap.
My main hats are a Borsalino Traveler fedora and a good Panama Fedora.
I do get a lot of looks from very old women when wearing a fedora – pretty sure they are recalling their long dead husband or father when they see the hat – but even teenagers with their baseball caps on backwards often give a nod and say “Nice hat.”
Hats? Never touch the things. 
I mostly prefer black fedoras. I have a cheap one I got at Express for $20, which serves as my knock around hat; I usually wear it with jeans and my black leather jacket. I also have several other, much nicer fedoras I’ve acquired from various places (Indiana, Copenhagen, etc.) that I wear for special occasions; I tend to wear those with my winter overcoat.
I own and wear about 3 dozen hats. You name it, I’ve got it!
Except a bowler.
Well, I’ve got three at the moment–a straw fedora for summer, a grey-plaidy stingy brim fedora (or maybe it’s a trilby? I’ve never figured out what makes a trilby a trilby) for fall and spring, and my blue-green wool fedora with a feather for winter.
The last is a bit too big, and I need to take it down to Pork Pie Hatters soon to see if they can adjust it. If not, it’ll be time for a new winter hat. Conveniently, they have this incredible wide-brimmed Borsalino there that I’ve been lusting after for months… would have it already, if it weren’t $300!
I have a black flat cap I wear backwards, so it looks kinda beret-like, sometimes when I play guitar at gigs. It’s good for bar gigs - not sure why; maybe because motorcycle riders sometimes wear backwards flat caps when they are off their bikes so I feel like I fit in better 
I have a crushable porkpie I enjoy wearing during the colder months.
Finding a hat that works is tough. I bought online for a whle - there are a number of sites with wide selections and competitive prices - but it took a ton of trial and error to find ones that work.
Sadly, there is still no love for the boater.