For those that chose to wear hats, what is your chapeau of choice?
For those that choose to wear baseball caps-frontwards, backwards or sideways-this isn’t your thread.
My hat is a gift given to me from my sister-in-law(Thank you again, Edie!), brought back from her trip to Ireland. It is a blue/grey Donegal Tweed flat cap from Shandon Headwear, and it fits both my head and my personality.
I have several flat caps, my favorite being one my gf brought home from Ireland for me.
I also have a hand crocheted Rasta-colored hat from a trip to Jamaica. It isn’t the type for controlling dreds, it’s more like a yarmulke.
I have three Panama hats, a gray and an olive fedora (the olive one is a Mallory by Stetson) and several flat caps in various tweets. Casual summer wear is often a boonie hat (khaki or navy) and casual winter wear is usually a woolen watch cap.
For other occasions I have a straw boater with a nice red band, a mad bomber hat, and several pith helmets.
High-crown, dimensional-brim feds: two, one brown and one gray.
Regular fed: one in black.
Panamas: one 600-line fino for dress, one $20 for summer daily.
Flat caps: one cheap corduroy, one kangaroo in black.
Pretty much wear only the last these days, and only when my hair isn’t so bushy it pops off.
I have a black trilby with a gray and white band which is my default, and two others, one tan and one straw. I wore the brown leather slouch hat that a friend gave me to walk the dog last night.
Today I am wearing my gray fedora.
Someone who I shall not name stole my tan Panama hat, but she looks too styling in it for me to object. My son gave me a sparkly silver little number that I have never had the nerve to wear in public.
As I have explained to my daughter the Fashion Maven several times, my hats are not stupid - they are post-ironic.
Tip o’ the hat to you,
Shodan
My go-to hat choices are the Outdoor Research Swift Cap* (for general walking around) and the Redhead Safari Hat (for hiking). Both feature lots of mesh and breathe really well.
Speaking of headgear, have any Doper bicyclists tried “Da Brim” helmet visors? I like the concept, but they look kinda geeky.
*yeah, I guess it’s basically a baseball cap, but what the heck
Harumph. When I’m not wearing the hat-that-you-chose-to-make-taboo, I have a leather Aussie outback hat similar to this. It’s great for fishing, hiking and general outdoorsy stuff. Very durable.
A grey wool flat cap I picked up in Dublin for cool days, and a Montecristi Panama hat I bought to wear with my white linen suit to my niece’s wedding in July for when it’s hot out. When it’s just plain cold, I wear a Peruvian hat.
I have a toque.
But then, every Canadian does. 
A white pith helmet. One version has a solar-powered fan in it.
I haven’t tried it myself, but I was on a long bike trip, and some other cyclists were wearing them. They loved 'em. Kept both sun and rain out of their eyes, but didn’t interfere with their vision. I’m getting one before my next multi-day bike trip.
I don’t wear a hat or cap. Although last summer, I went on vacation and was touring in temperatures over 110 degrees, and I really needed something on my head, so I bought a baseball cap at the place I was touristing at, and I wear it in the mornings when I walk, to keep the sun out of my others. Otherwise, no.
My first choice is my tan Stratton S-42 Sheriff style (no cord or acorns).
http://www.strattonhats.com/images/products/s42_large.jpg
2nd choice is a Henschel Aussie Breezer.
http://www.henschelhats.com/hats/breezer-collection/#prev
Then there are several boonie hats in various colors and my favorite baseball cap -
http://www.ebay.com/itm/Husqvarna-Run-Forest-Cap-Camo-/391572236247?hash=item5b2b8627d7
I go for a Borsalino beaver fur felt fedora. Bought it at J. J. Hat Center on Fifth Avenue.
A selfie of grim-faced me in my fedora on a chilly 7F morning
I never was a hat guy, but after having to accept the reality of the thinning of the troop on the Northern Border after several annoying scalp sunburns, I searched High and low for something that didn’t make me look like a jackass and was durable and would survive a fall in the lake, and finally got something damn close to this.
which works perfectly and doesn’t make me look particularly stupid.
I got a nice outback hat from my sis-in-law’s Australia trip.
I’m trying to convince her to go to Russia next year-I could use nice winter hat. 
I love my Tilley hat. I have an LTM5 in olive. It is great in the sun and rain, walking around town or hiking a mountain, land or sea, and it’s Canadian made!
Black flatcap, backwards. Kangol porkpie.
Both mostly when I play guitar. Or when grocery shopping with bedhead.
I should wear a hat more becoming than the baseball cap I do, but anything I’ve seen just feels hipster-lite or pretentious.
Join me in wearing an Akubra, then! They make your entire outfit look far cooler. 
