Children say the darnedest things sometimes. :rolleyes:
To answer the OP…
Being an “old man”, got a fedora and a porkpie that I wear interchangeably during the colder months. I also have a baseball hat I wear in the Summer to avoid heatstroke.
Not a chance. I’ve got great hair and a hat would conceal it.
Oh, yeah, one more important reason to wear a hat anytime I’m outside. I burn fairly easily. And scalp sunburns SUCK.
I love wearing hats, I have a driver cap that I wear all the time, I have a nice wide brimmed fedora, a top hat, a plaid trilby that is distinctly an ‘old man’ hat, a really old beat up hat (which my brother refers to as a Jed Clampet hat) that I imagine must have started out as a fedora at some point in its life, and several others. I could comment that my age proves that it is not just an ‘old man’ thing, but seeing as I dress in suits or cardigans whenever the weather permits might make my opinion less valid here.
In England, if a bloke wears a hat these days he’s considered to be a bit of a twat. A mate (from Australia) turned up at work a couple of years ago wearing a fedora and everyone laughed.
My dad always wore a trilby - he wouldn’t leave the house without it. Before he adopted the trilby, he always wore a flat cap; he was born in 1915.
I’ll wear a straw hat (fedora) in the summer.
I have a felt newsboy cap, a black cowboy hat and sort of a eurostyle beret for winter.
A few years ago I had business in Cambridge. Since it was January, I wore my fedora for the whole week, including a train trip to London to spend a day at the British Museum. I felt out of place with my hat. Several people commented on it. I only continued wearing it figuring that folks knew that I was a yank, so they would let it slide. Besides, it’s warm.
I am not an everyday hat wearer, but a frequent one.
Summer: cotton baseball hats (I’m a sweater, so they get soggy), or for heavy sun or music gigs (I’m a sax player), panamas.
Winter: baseball hats, floppy Irish newsboy’s cap, or for music-related activities, felt snapbrims.
I have a bowler (derby), but only wear it with a tuxedo, and then usually only on new year’s.
My messed-up right eye demands that I wear a hat when the sun is out. I have felt fedoras in brown and charcoal gray, and a Stetson canvas one.
I have a black cowboy hat in the “gambler” style (I’m too tall to wear a high crown) that a friend bought for me at the Stetson works. I’m not a cowboy, so I feel sheepish about wearing it.
In straw, I have a broad-brimmed thing with a kangaroo emblem. I also have a white Guatemalan masterpiece that’s too dressy for most of what I wear in the summer. It looks like it ought to be on Ricardo Montalban.
I have St. Louis Cardinals uniform caps in home (red) and away (navy.) I also have an L.L. Bean long-billed “swordfish” cap.
I have a very nice black beaver-felt fedora that looks quite snappy with my black suit, but it’s far too dressy for everyday wear. Since I only wear it when I’m dressed up, it doesn’t feel like an affectation, and I generally get compliments on it.
Since places these days don’t have hatracks, hats are a tad inconvenient because you have to carry them when indoors. (Yes, it’s rude for men to wear hats indoors. No one seems to get this, it’s quite appalling)
I have a cheap red felt Fedora from when I worked at Red Hat Inc. I never wear it.
I also have a well ventilated leather hat that I picked up in Australia. I wear it whenever I want protection from the sun. Unlike a baseball cap, the full brim protects my face, ears, and back of my neck. It’s getting a bit stained from years of use, but it still works.
My rainhat is dark brown oilskin, also Australian. It’s not formal at all, but quite functional. I’d never wear it unless I was expecting a downpour.
And my last hat is a bucket hat, specifically for sun protection when I’m rafting because it floats and had a waterproof compartment. But I think that’s falling into the “sport hat” category that the OP prohibits.
I recently lost my well worn felt fedora. Now I have to break in a new one. In the summer I love to wear straw dress hats. They always make me feel like I’m on vacation.
I like fedoras. I have three. The only issue I have with hats is that at my age (late 40s), women seem to assume I’m wearing a hat to cover my baldness. I’ve surprised more than one when the hat came off.
I have a porkpie that I wear a lot when I play with my band.
I have a fedora that I wear occaisionally.
Are the “affectations?” Don’t know and don’t care.
People are always going to talk about something. Bite me. I wear what I want.
I have a well-worn black fedora that I break out when the weather gets cool and wet here in Michigan. I get a lot of compliments on it, and like previous posters, I’m easy to pick out - “oh you know Genghis Bob; he’s the guy with the hat.” It’s a great insulator, all I need to keep the top of my head nice and warm and dry in even the worst weather.
In the summertime I’ll wear an Irish walking hat when I have to go out in a downpour.
I like hats. They’re much warmer than an umbrella, and they leave a hand free.
I’ve got a tail coat (tux) and top hat, and am told that I look smashing in them, but I’m not entirely convinced.
Normally, I don’t even wear baseball or trucker caps as I’ve got a size 7-7/8 melon and like several others here, even at the last notch, adjustable caps are too small.
When I wear my topper and tails, I suspect people are more startled at my exceedingly uncharacteristically dapper appearance than anything else.
My noggin is so colossal that I’ll put my hat size up against anyone else’s in this thread. Really, truly huge.
However, I did manage to find a couple that fit pretty well at the Village Hat Shop, which has a “big head” section. I bought two canvas Aussies, one with a mesh crown, mostly for working in the yard (I sunburn easily). I wore the mesh one daily this summer when my wife and I went to Disney World, where the sun was truly brutal, and it worked out quite well.
Anyway, I had to order the “3X” size for both hats, and by gadfrey, they actually fit. If only I had the money for the leather Aussie with the crocodile teeth…
Mind if a lady chimes in? Gentlemen in hats are definitely attractive. Wearing a fedora conjures up images of Indiana Jones or Humphrey Bogart and shows a man’s got a bit of style and flair to him. Definitely worth a second look! Then again, I’d expect nothing less from a guy named “Johnny L.A.”, although a pork pie doesn’t quite suit the image as well.
CJ
Female owner and wearer of multiple hats
Just wait ‘til I get my MGB back and start crankin’ the ska! 
I have 3 hats in heavy rotation:
A Pearl Izumi mesh running cap (sadly discontinued) that fits just right and has superior ventilation.
A Tilley wide-brimmed hat–great for hiking.
A Boston Red Sox cap that I purchased at Fenway last year. (They beat the Astros that day, 9-2…) This had gets more comments than any other article of clothing I’ve ever worn.
Can I assume felt fedoras are waterproof, or do I have to look specifically for “waterproof” hats if I want one?
I’d like to try the overcoat & hat combo one of these days.