When is it appropriate to wear a hat? I remember in high school I was always annoyed by those guys who would wear fedoras with regular clothes in a hipsterish manner. If you go to someone's house or a restaurant with a hat, what do you do with it when you take it off?
Wherever you put your coat is where you put your hat. Hang it on a peg. Put it in a closet. If you're in a restaurant and there's an empty chair, put it on the chair. And good for you for taking it off - the etiquette is, women can keep their hats on inside, men shouldn't. The only exception seems to be western hats (and really, only in Texas). Generally considered to make such a wreck of your hair, it's more polite to keep it on.
As far as when to wear a hat/what hat to wear, here are some pretty basic guidelines:
Fedoras (I'll just lump all dress hats in here): Wear 'em with your suit. If you're not wearing a suit (or at least a top coat over a nice sweater and shirt & tie), you're too casual to wear a dress hat. This results in most people who wear a fedora looking, as you put it, "hipsterish". Kind of like wearing black dress shoes with jeans (fedora with casual button-down/slacks) or black dress shoes with sweats (fedora with t-shirt and jeans). If you're just wearing a normal casual outfit (OCBD shirt/khakis, let's say), then it seems to be pretty acceptable to wear an ultra-narrow brimmed fedora (these are the kind that are popping up at Wal-Marts and dep't. stores the last couple years), but stick with a more casual fedora (i.e., not a nice, black, felt hat, this is where a soft tweed fedora with a small brim might come in handy) or a more casual type of hat altogether (like a flat cap, or, if it's spring/summer, a panama/boater, or any type of light, straw/woven hat).
As far as flat caps (A.K.A driving caps, ivy caps, newsboy caps, golf hats, cabbie hats, cheese cutters*), you'll look a bit hipsterish/"edgy" if you're wearing a t-shirt. These are my favorite type of hat (a good one is super comfy and looks great on my odd head), but they often have streetwear association (esp. when worn backwards) or punk/skin/edgy-try-hard association (esp. if worn with a graphic tee or work shirt, Docs, and/or suspenders/braces).
Baseball cap: If you're playing baseball, this is what you should probably wear. Going to a game? Sure. Wearing a suit? You can, and many do, but it's not a "classy" or "gentleman" look. If you're trying to stay away from the frat boy/bro look, leave ball caps for fishing or going to a ball game. Wear it while you sit on your porch and smoke a pipe while listening to your team crack some bats over the radio.
As far as when to wear a hat, it used to be inappropriate for a man to go out-of-doors without a hat on. Now, aside from inclement weather situations, it seems more the norm to go hatless. The rule is generally: outside-don your hat. Inside-take it off.
Fun parts: A sporting event is generally considered "outdoors", even if you're at an indoor arena (if it's an outdoor sport such as football or baseball, for example). Airports/bus & train depots/etc are considered outdoors, even when you're indoors there.
If you're eating or sitting down with someone, take off the hat. Doff the cap to a lady as you're introducing yourself.
Generally, taking off your hat is a sign of respect. You're supposed to take it off when you enter a building out of respect for the present company.
As far as where to put it, if you're sitting down to dinner, there ought to be a coat rack where you can hang your coat/hat. This is often not the case, so I can't help you much there, except to say, when hosting people, make sure you offer to take their hats and coats and put them somewhere that people won't mess with them.
Wear a hat whenever you want or need to. What TYPE of hat you wear, is up to you.
Under all circumstances, a hat stays on the head, unless a place has been provided for you to hang it/place it. Or if someone asks you to remove it (eg: cinema). In a restaurant, the same thing applies. It stays on your head unless there's somewhere to put it.
Always a nice touch to take it off when introduced to a lady, even if outdoors.
Great info, Joshua, do you have some reference text for all that? I looked in the few I have, not much other than what I said above.
There are some good sources online...
This one is amusing....
Inasmuch as I wear hats much of the time, I have a few basic rules that I adhere too.. However, what you wear and how you wear it is part of the basic etiquette too.
Don't wear a hat at the dinner table, home or restaurant. It doesn't matter if you're balding and insecure. If I can get past your face, you bare bean is tolerable. The only exception is if there is absolutely no place to put the hat. Usually, there is (but not always). On an empty chair, on the bench seat you're sitting on, or a coat hook if provided.
You may elect to leave a cowboy hat on in a bar or tavern, which I advise as some idiot will invariably spill something on it, or feel compelled to have a look at it. If some drunk decides to pluck your hat off of your head, it's within the rules of manly decorum to crack a heavy beer mug on the guy's temple. Some things really are sacrosanct.
Slightly different rules apply to a common fedora, such as it's usually not okay to wear one at the bar... Remove your hat when meeting a lady indoors. Tip your hat as a greeting to lady outdoors. Don't tip you hat to a man, unless the intent is to insult (especially in the southwest).
Ball caps are a bit different, in that there is no such thing as a classy ball cap. I'll wear one from time to time, and I treat it like any other hat, except that it's much easier to store. Still, there are ball caps of different social value. Nothing is a dorky as an unbent bill, or God forbid, the latest practice of leaving the NFL, NBA or MLB sanctioning sticker(s) on. Trust me, no one of consequence gives a shit if it's a $10 cap or a $30 cap. There are no classy ball caps. Unless you just removed a catcher's mask, the bill goes in the front. Wearing one sideways or half sideways may be a fashion statement among dweebs, but the only people worthy of impressing, won't be impressed. Because of what I do for a living, I've been to many high end events, where nearly everyone has money or reputation, or represents a big dollar corporation. Award dinners, charitable events, Wine and cheese gatherings and business conferences. At some of these, especially summer outdoor events, you'll see ball caps, but rarely one on backwards or sideways. Panama style straw hats are common in these social circumstances.While a hat doesn't necessarily make the man, the wrong hat worn the wrong way can diminish the man.
Knit hats... If it's cold out, they're fine. If it's 90° in the shade... Seriously... Anyway, take it off when you enter a non-public place, or restaurant. Obviously, you can't readily tip a knit cap...
Flat caps are also very nice, but should be treated like a fedora. Unless you're Samuel L. Jackson, the bill should be in front. Jackson gets away with it because, he's an ignorant celebrity. If ignorant celebrities had to account for their dress style, very few would ever leave their homes. Some might argue that they are making a statement. Indeed, they are. Others may feel that they are on the cutting edge. That is, if the back side of the fashion knife has an edge. Of course, No one in Hollywood does hats worse than Johnny Depp...
Now, all of that said, some folks will wear their hat whenever and were ever they wish. Just remember, that as much as a hat says about you, how you follow the basic rules of hat etiquette says much as well. Of course, I could be completely full of baloney...
Corey, I confess that some of your advice actually made me laugh. But it's good advice. Very good. But you write it in a way which made me chuckle. Especially the bit about smashing a beer-glass on someone's head!
Check out Optimo Hats.com A lot of good information.
Hat etiquette is very debatable because society has changed quite a bit since the time in which it was common for men to wear hats. I've started wearing fedoras recently. I don't feel it necessary to always wear a suit with them. I generally wear them with a nice button down shirt, slacks, sometimes a tie. But, I'll also wear them with dark jeans and button down shirt. It's up to you. There are some hat wearers who will wear a homburg with a t-shirt. The most important thing would be to wear the hat, and not let the hat wear you.
As far as etiquette... do what works for you. General rules are that you always remove your hat in a home, office, church or restaurant. Exceptions are if you are in a lobby, hallway, elevator (unless a lady is also in the elevator - then remove your hat) or if you are eating at the counter in a restaurant. It is also not necessary to remove your hat in a store or similar public place. If you encounter a female cashier at the check-out, its generally not necessary that you remove or tip your hat because you are separated by the checkout counter. If you meet a lady, tip your hat. If you have a conversation with her, remove it. If you begin walking together, you may place the hat back on your head.
These are what was generally accepted practice in the hay-day of hat wearing. Today, many people don't know proper hat etiquette, so you have have more room for error. Some of the rules would be considered antiquated by certain people... basically, decide what works best for you.
You can wear a hat inside a restaurant, but take it off when you sit down at your table. I usually hang mine over my knee if no spare chair or rack is present. Always take off a hat when you come into a home, I usually find a good out of the way place to put it. Leave it upside down, both for luck and so you don't rumple the brim. Never wear a hat into a church, whether you're religious or not it's a bit churlish. (I'm not sure where old ladies got the free pass on those enormous fruit laden sombrero's they wear in there.)
Never have your hat on during the playing of thenational anthem, unless you are in uniform of some sort and are on parade during it. I take mine off out of respect when I'm visiting our neighbors in Canada as well.
Hats are fine in public spaces, like stores, bars, or malls, but I take mine off when I'm in a theater. I'm a bit taller than a lot of folks around here, and having to look around my frame plus my 3" brimmed hat is a bit much to ask.