Spinning off from this thread…
I’ve recently taken to wearing a porkpie hat. (I haven’t had the opportunity to wear my black felt one yet, but I wear the coconut one a lot.) How about you? Would you – or do you – wear a fedora? A Homburg? A bowler? Why, or why not?
I’m interested only in ‘dress’ hats in this thread – no ballcaps, sports hats (such as the ‘Sonora Sombrero’ or ‘Seattle Sombrero’), or (and yes, I’m aware they’re considdered ‘dressy’ in some places) cowboy hats.
When late fall comes around, and I’m walking in the chill air, I occasionally sport a beret pulled jauntily to one side of my head. My fall attire is rather European anyway, so it’s not completely incongruous.
I love a good hat, but unfortunately my head is bigger than the average hat sold in the US. I know that I could go to the internet and find a store for big headed men, but that is more effort than I would normally spend.
I’ve really wanted to wear a Hamburg, for some time but my hair is a disaster after removing a hat. Although lately I’ve been wearing my hair very short so maybe it could work now, hmm.
Thanks for bringing it up, Johnny.
I definitely want a hat. Maybe a fedora, maybe a bowler.
I’d love a good fedora with a narrow brim, or a trilby. But I haven’t found the perfect one yet, or a cheap-enough one.
I’ve got a newsboy cap in Broncos navy blue. It’s not really a dress hat, but it works at times.
Other than that, I wish I could pull off the Humphrey Bogart look. Trenchcoat, hat, handgun, hip flask–you know, the works.
My father wore a fedora during cool weather, up until he died in 1985. Of course they were more fashionable when he started wearing them in the 1930s. But I thought it looked cool, unlike the straw cowboy hat he wore in the summer.
I love me some good hats, but in L.A. it’s almost never cold enough to make one necessary.
I do recall about 12 or 13 years ago we had an unusually cold winter for L.A., and at that time I used to take long walks at night. My fedora came in very handy then, but I don’t get much chance to wear one now.
I agree with the OP that hats look great.
Like Khadaji my head is too large for widely-sold hats to fit. Those adjustable ball caps don’t fit even at the last notch. Besides, the rest of my wardrobe isn’t really up to hat standards. If I could find one that fits, I’d have to buy outfits to go with it.
I never go out without a hat, though in summer it’s baseball caps. But in the winter I wear a nice little newsboy hat made of fleece. I’d love to get a fedora, but they are just too expensive.
I just have to say, I love my fedora. I wear it all the time.
I have worn a fedora during the cold months for the past decade or so. It took a little courage to wear it the first time since I was in my mid 20s and felt self conscious.
These days I can’t be without it whenever I have on a jacket. I get compliments all of the time and folks at work recognize me as the guy with the hat.
There is the added plus that when it is pouring down buckets I need not carry an umbrella – a leather jacket and fedora are enough for all but horizontal rain.
Come to think of it, I have a fedora round here somewhere. It’s packed carefully in a box. Now if only I could remember which box…
Hats always remind me of 12 O’Clock High. The film starts when Dean Jagger is buying a hat, something that he’d do very quickly at home but which gave him a very nice conversation with the haberdasher in England, and he stope to check himself out in a store window. He sees the Robin Hood toby in the store…
I don’t think I’ve ever seen a haberdasher’s IRL. (Though I was given a few links when I was looking for my porkpie.)
I could see a fine hat looking good with a matching suit.
The problem with hats (specifically dressy hats, as specified in the OP) is that you get the sense that guys wear them as a way of saying “Look, I’m wearing a hat!”
I have no idea what a porkpie is, but I wear my black fedora all the time in the winter. (Or whenever it’s cold. Or raining. I have no use for umbrellas.)
It goes nice with my overcoat. And I can amuse acquaintances by finding unlikely substitutes for hatracks.
Same as Khadaji and Otto, I have a freakishly large head, so hats don’t fit me. Which is fine, as I agree with RickJay on this:
Bingo. On any man younger than about 70, the semiformal hats under discussion strike me as rather silly affectations.
I have three hats.
Friedo: This is what a porkpie hat looks like.
Yep. I would never wear a hat, except my ballcap (old school Angels with the lower case “a”), and if any of my friends wore one the rest of us would likely mock them until they took it off. Non-ballcap hats (or ski caps in the winter) are what the old men wear on cold days on the Metro. Or younger people trying really hard to look “hip.”
Note that “old men” in my view represents any in their late 30s and up. 
I began wearing a hat in High School. It was an affectation. It was a white canvas fedora with a loud band. I liked it. I also found that it would shield my sunglasses from rain, snow or glare, if needed.
I’ve worn hats since then. Some were more dressy than others.
The worst hat I ever had to wear was the Dixie Cup of the Navy’s blue shirt scum. It just looks awful. For the past several years I’ve alternated between either my old Navy ballcaps - I can sweat in them, or Stetsons. Since one of the ways I justify my hats is the keeping glasses clear - a wider brim is better. Of course that got me mixed up, in NYC for being with Blues Traveller. (Quick hijack - is there a polite way to explain you’re not the celeb someone thinks you are without making them feel stupid? I never found it.)