A black felt Fedora kind of thing that has cloth strips on the sides to tie under the chin to keep it from blowing off (and keep ears warm). I also have a similar white one, but it’s gotten kind of mushed and dirty.
I’ve got a black fedora that I only wear when it’s cold. It looks very out of place around here where baseball style caps are the norm.
I rarely wear a hat. When It’s really cold and I’m outside for a while, I’ll wear a head band and use a hooded coat to protect myself. That’s all I really need.
I do wear a straw hat if I’m out in the sun for a long time. I also will wear it for my Wifes tri races. I’m pretty tall, put a straw hat on me and I’m easy for friends/family or my Wife to spot in a crowd. It works quite well. Just look for the tall guy in the straw cowboy hat.
My Wife is about 5’2”. Dress her in your basic athletic gear and mix her up with a thousand or so other athletes and I just can’t find her. She has to look for me. The straw hat works great.
I have an ushanka like this one. ‘Some tea, Captain Ramius?’ I rarely wear it for two reasons: First, it’s huge. Very thick mouton. Second, it hardly ever gets cold enough around here to wear it.
That Akubra looks nice. Sort of a cross between a fedora and a cowboy hat.
I have a khaki ball cap with similar flaps in the back. I wore it a few times when I lived in the Mojave Desert and liked to drive the old Willys around. But I found that a surplus boonie hat worked just fine. The flap hat is packed away in a box somewhere.
Wear it anyway. Make a statement. Like, ‘Hey look! I’m wearing a fedora!’ 
I have a tendency to cut my hair very short, and then not cut it for six or eight months. Sometimes when my hair is shaggy I’ll wear a beret. It’s a black army-surplus one. I cut the stiffener (for the badge) out so it doesn’t look military. When we were working on a film I found that it kept my head warm, but since it didn’t have a brim it was better for using the camera than the pork pie.
I like bucket hats. Very Hunter S. Thompson. I only have one, but I haven’t worn it in years since I like the felt hats.
What kind of hat don’t I wear?
I usually wear one of those brimmed knit hats from Dickey’s. The bill on the front keeps the sun out of my eyes. If it’s a bit warmer, I wear a quilted billed hat from I. Goldberg’s. I believe it’s made by Bronner.
In the summer, it’s usually a fatigue cap or a ball hat.
I own what I think is a trilby, and a bowler, and a very cheap (Halloween-wear) top hat.
Us bald-headed guys gotta keep the sun off the melon. 
Hat too big, or head too small? 
A trilby is similar to a fedora, but with a narrower brim. Actually, some of them almost resemble pork pies or bucket hats.
Kangol herringbone trilby. I think of this style to be a ‘mod’ trilby.
Here is a c.1950 photo of a man wearing a more fedora-style trilby.
Jude Law wearing a trilby.
Love hats. Used to wear my grandfather’s as a kid, and never got out of the habit. Aside from novelty or historical hats (1890’s British pith, Scottish feather bonnet, etc.), I use a number of hats for regular wear. These include brown, dark gray, and green fedoras, three straw fedoras, a light brown Borsalino, gray felt porkpie, straw porkpie, “Sam Snead” snapbrim, Panama (Ecuador) hat, herringbone Trilby, and a drawer full of large brim fabric hats for hiking, gardening, and the like.
Did I say I love hats?
Right now I wear a silly toque with ear flaps. In summer I usually wear my Tilley (I actually wore out my first, and they sent me a new one), but I’ve also added a Brixton Stout to my wardrobe.
Lack of velcro-like hair to help hat defy gravity at a non-Euclidean angle. 
If I wear a hat, it’s a Barmah. Usually only when hiking.
Or if I want to go more “formal”, I have a leather hat with a flat brim.
Several. I got a nice little wool hat with a brim at the House of Blues in Vegas. I like the way it looks.
I also have a fleece hat in that Irish style with the crown snapping to the brim. Looks good and has ear flaps when it’s especially cold.
On warm, sunny winter days, I usually wear my New York Americans baseball cap. I also have a beat up L.L. Bean gray wool cap for shoveling snow.
In warmer times, I have a bunch of baseball caps.
Oh, where do I start? I’m a St. Louis Cardinals fan, and I have the on-field cap in home red and away navy. There’s the L.L. Bean swordfish cap with vents and a big bill. An old railroad stripe cap is for yard work.
I have fedoras in charcoal, brown, and a canvas tan one for light rain.
In straw, I have a wide-brimmed plantation hat in tightly woven white. It looks like Guatemala’s finest, but it was made in the USA. Less formal is a cheap Chinese hat that’s almost a cowboy hat. Oddly, it has a little brass kangaroo on the band. There’s an open weave hat styled sorta like a pith helmet. It looks very much like the old summer US Post Office hat.
For winter, there are two. The mainstay is a Polartec hat. Picture two home-plate shaped pieces sewn together. When I put it on, it covers my ears and has a little pointy rooflike part at the top. If I wear it just above the ears, the red and grey hat makes me look like the biggest elf in the building.
When it’s warmer, but I might have to cover my ears, I wear an L.L. Bean hat designed by a mountain climber. It’s a short-billed cap in fleece-lined windproof nylon, with folded up earflaps that can be lowered a little at a time. Because of the close-fitting crown and short bill, it doesn’t look Elmer Fuddish. :rolleyes: I imagine it would get tiresome to have strangers coming up to do their best Elmer, saying, “Be vewwy, vewwy quiet. I’m hunting wabbits.”
Not a hat but a old brown sheepskin ushanka, now in the winter. In the summer, often an Elbsegler.
Mostly, I don’t. When I’m out in the sun a lot, I’ll wear a bucket hat. In cold weather, I generally wear a hood, though I also wear woolen ski caps. I’m not very fashionable.
The only hat I wear (other than golf cap on the links or knit skullcap in winter) is a tweed cap, with ear flaps that fold down. Doesn’t give me as bad hat-head as a skullcap.
When not used, the flaps fold up into the hat, and it looks just like a tweed cap. They can be tough to find. Last time I saw them, I bought 2.
Sorta like this. Used to have one with thinsulate. That was nice and warm.
I crocheted up my very own version of this hat (the photo is the one provided by the pattern designer… mine was made using a curly brown/beige/cream variegated wool, so it’s a bit fuzzier than the one pictured)
In Ohio winters nothing beats my black, wool beret, round the house my red wool fez keeps me snug.
In summer I have my brown fedora, or my straw trilby.
Perhaps my grey trilby if I’m in an 1960’s-IBM mood.
My British 1885 khaki colonial sun helmut is fun to wear at picnics or camping.
While mowing the yard I have my Japanese conical straw hat.
Also a black wook baseball cap with no logo, very warm.
Oh, and 2 roman centurian helmets for when the mood strikes, actually, if I started to list all the historical headgear I have it would be a major hijack.
Damn, I love hats.
In winter, I wear a gray wool knit cap with a red stripe. Or at least I did until last week, when my wife commandeered it for her own use. So now I’m not sure what I’ll be wearing.
In other weather, I wear a felt Golden Gate Hat Co. cowboy hat that almost matches this model. Mine is called “The Coyote,” though. I’m guessing they don’t make it anymore. The thing is almost 12 years old. (I need a new one…)
None usually.
If it’s raining and I need to be outside I wear a camo cap like this one. I also have a plain brown & green baseball cap I used to wear backwards along with my face mask when playing paintball.
