Oh lord no, nothing screams 40 year old middle manager, or soccer mom like those hats.
My dear old Dad had come to terms with his inpending baldness, he had plans to have a Ben Franklin look, bald on top and shoulder length on the sides and the back. And he would have done it, too, if he had not died in that accident.
Or, “I’m a stoner”.
I’m firmly of the belief that Men Should Wear Hats In Public.
I haven’t worn a baseball cap since I was 12, but I do regularly wear an Akubra Stockman’s Hat, especially in the Summer or when I’m out hunting.
I’ve also got a rather spiffy Foreign Service Khaki Pith Helmet that I’m giving to wearing at the rifle range when I’m shooting my Martini-Enfield .303 rifle. 
And, for Winter (not that we have it in Queensland, but Winters in the South Island of NZ were and are bloody cold!), I’ve got A Russian Officer’s Fur Ushanka (and yes, it has the badge on it!)
The thing is not to feel self-conscious about it. If you embrace the Hattage, people will see the Hat as part of you, not something that identifies you as part of some sub-group.
Of course, I’d also add that you probably shouldn’t be wearing a flat cap unless you drive a London Black Taxi and have passed The Knowledge…
A winter hat. tight and average.
…Maybe a tassle.
I’d actually say they’re the t-shirt of hats. People use them in order to alert people that they may have …
[ol]
[li]Been to Cleveland[/li][li]Served aboard the USS Walter Mondale[/li][li]A penchant for looking at women’s breasts[/li][li]Worked for UPS[/li][li]Some sort of affiliation with various universities[/li][li]A belief that America is peachy keen[/li][li]Certain amorous feelings for New York City[/li][li]A friend who buys cheap gifts[/li][/ol]
and so on and so forth.
A trilby is absolutley the most serviceable of hats. You can wear it “up” at a jaunty angle for that Sinatra-“ole blues eyes is back”-insouciance, or down at eyebrow line for the “Joe Friday hardarse” look. A damn fine hat, the tribly
mm
I occasionally wear a hat like this but without the flower.
All I can think of that it says about me is, “I’m a girl!”
probably not the message you want to send.
a friend of mine (male) always wears a newsboy cap when he goes out. I think it’s very nice-looking on him. It’s not a “freak” hat in that you wouldn’t see his hat and know anything about him, but it’s not everybody’s style.
sorry to double-post, but upon further exploration I found this site…
There are loads of hats there. You’re likely to find SOMETHING you can live with. I’m not terribly up on grown men’s fashion, I’m afraid, but I do like some of those hats.
There’s probably not a damn hat in the world (or any other article of clothing) that someone, somewhere, won’t try to pin with some kind of label.
Wear what you’re comfortable with, and don’t worry about what anyone thinks. Just find a hat you think is really, really cool. Then wear it with pride. 
I wore a captain’s hat kind of thing once, and many people said it suited me. I’ve kind of wanted to follow up on that and get one. But there’s just so much baggage associated with something so quirky, that I’m reluctant to do so. I’m very deliberately dull in most ways, so to do that would be… out of character.
I think I’ll stick to my fez, and pith helmet.
Please don’t wear a baseball cap. That goes for all of you. Unless you’re playing baseball. Thank you.
I’m fond of wearing a panama in the sun. But I like the ushanka.
I’m fond of wearing a panama in the sun. But I like the ushanka.
And if you insist on wearing a baseball cap anyway, the bill goes towards the front, unless you are currently playing catcher. Ta.
Is “Canadian” a subculture? If not, I advise a tuque.
Ok, now that I look at my links again there is a difference between the Lands’ End hat and the logoed examples I provided. They looked the same to me at first, but now I agree with you about the Lands’ End hat.
So what kind of hat are those two examples? Are they considered baseball caps? All I know is that’s the style of hat I see all kinds of people wearing around here, and that’s what I would consider to be a “generic” hat.
Guys who have shaved their head often wear one of those skull-cap things. I don’t think that makes you a part of any subculture except “cold headers.” If going bald is a reason for hat searching, a full shave seems like a good way to go to me.
Yes, that’s a baseball cap. They are the generic hat in the US. Some are nicer than others, but all of those are baseball hats.