Hat Shop

""No one knew better than Granny Weatherwax that hats were important. They weren't just clothing, hats defined the head. They defined who you were. No one had ever heard of a wizard without a pointy hat -- at least, no wizard worth speaking of. And you certainly never heard of a witch without one... Hats had power. Hats were important.""

- Witches Abroad

Hats have connotations. Even nice ones. Check out this page if you're looking to give your character a little extra something to make them stick out in the mind of your audience.

Hat Etiquette
But first, be aware that there are rules that you should follow, at least for stories set in the West. If your character is male, and his hat is a general purpose, normal-weather item and not part of their uniform (or a character quirk), and especially if you're striving for period-accuracy, you should know when they should and shouldn't have it on.
 * 1) A hat is always worn outdoors.
 * 2) However, a hat must always be taken off when stopping and speaking with a lady.
 * 3) Likewise, unless it's part of a uniform, it should be removed when a national anthem is being played, except as a show of protest/bad manners.
 * 4) A hat is not generally worn indoors.
 * 5) However, it may be kept on in an indoor public space, such as a a store, as long as your character doesn't work there. If the space transitions from "public" (hotel lobby) to "private" (corridor on a room floor), one is expected to remove one's hat at that time.
 * 6) If they do work there, then it's acceptable to wear an outdoor hat until they reach the place where they'd normally take off their coat.
 * 7) A hat is removed in an elevator, except when it's too crowded to reasonably do so.
 * 8) A hat is always removed in a restaurant, because it's bad manners to sit down to eat with a hat when indoors. (Keeping your hat on at picnics and cookouts is okay.)
 * 9) The "remove your hat to show respect" rule is specific to Western-European-derived etiquette, however. In many other cultures (e.g., Middle Eastern), keeping one's head or hair covered is considered more respectful (humble, modest, etc). This difference is most visible in connection with religions other than Christianity, many of which either require their adherents to wear hats at all times, or require all visitors to the place of worship to cover their heads.
 * 10) One tips one's hat to show appreciation, or to greet someone else on the street. For strangers and acquaintances of lower status, this is generally a small nod while lightly gripping the brim with the tips of the thumb and first couple of fingers. For close friends and acquaintances of higher status, one also doffs one's hat; generally, this means raising it just off the head and putting it back down, via the brim if it's stiff (as on a top hat or bowler), or the crown if it's not (as on a fedora). The gesture is increasingly exaggerated as the level of gratitude or the status of the other person rises, but beware of taking it too far: if anyone who isn't hired help makes a show of removing their hat in a big arc and bowing deeply, they're just being affectatious.
 * 11) Properly, one should not wear a felt hat in the USA after Straw Hat Day, the day when everyone switches from felt to straw hats, often in unison. The exact date varies regionally, with many regional populations believing that the day has been federally fixed at May 15, but other areas always use a certain day of the week, and other areas prefer dates as early as April. Similarly, a straw hat should not be worn after mid-September. The only constant for the dates is that felt hats are never worn between Memorial and Labor Day.

These rules may be freely ignored for the sake of Rule of Cool, as they always have been in fiction. And as noted above, always remember that like most rules humans come up with, ones involving etiquette are not universal.

Hat Size
Nothing points you out as a hat neophyte as using such terms as "small", "medium" and "large". Proper hats are sized according to a more precise system that varies by country. Note also that a proper hat does not sit on the ears; if it does, then it's too large. A properly fitting hat (lightly) grips the head itself just above the ears, without sliding down of its own accord.
 * US sizing is calculated by dividing the head circumference (in inches) by pi, then rounding up to the nearest eighth.
 * UK sizing is calculated the same way as US sizing, but subtracting an eighth from the final result. A US 7 3/8 (the most common hat size for men) is a UK 7 1/4. This puts the hypothetical "size 0" at a head circumference greater than zero (a.k.a. "no head"), akin to the US / UK differences in floor numbers and shoe sizes; practically speaking, however, it just creates headaches for people who buy things on Internet auctions.
 * European sizing is the simplest system, based on the wearer's head circumference (in centimeters) rounded up to the nearest centimeter. This makes it something of a "universal" for modern hat sizing (such as the market is, these days). This system technically makes each size slightly larger than its US/UK counterpart, but they're usually adjusted to match in dimensions. A US 7 3/8 is a size 59 in this system.
 * Italian hats are often sized in "punti", whose method of calculation is based on arcane, dark arts lost to the ages (read: I don't speak Italian and searches of English-language web pages turn up nothing). It appears to have some correlation to crown height as well as head circumference, but an Italian-speaking Troper will need to chime in on this one.

But with that out of the way, let's get on to the hats themselves:

Kinds of hats

 * Balaclava (ski mask): Some sort of criminal; especially bank robbers, people who rob convenience stores, or terrorists.
 * Much more rarely, skiiers.
 * Or spies.
 * SWAT officers, but only if they're nameless and unimportant.
 * Bandana tied around head: Pirate, gang member, law-abiding teenager trying to look like a gang member, Antoine Dodson, or Solid Snake.
 * If it's a Hachimaki and you're in The West, you're a karate apprentice.
 * Wearing a baseball cap tells people that you're adventurous, heroic, slick, and an all around cool guy, or that you want them to think of you that way—the latter especially if you wear it backwards. The wearer of the baseball cap is usually either the good hearted leader of the group or a Jerk Jock. In a Lady Land or one full of ambiguously-gendered persons, they're probably male. If worn by a tertiary character, it means that the writers were not confident enough to trust that they could establish the character's place of origin without a regional symbol on his forehead.
 * "Trucker Hats", logo baseball caps with a plastic mesh back, are worn by—surprise—truckers, but also ironic hipsters and farmers.
 * If the cap is navy blue and has a ship on it means someone is either in or connected to the U.S. Navy.
 * Often associated with chavs in the UK.
 * Turn it sideways = gang-member, douchebag.
 * Turn it inside out and either backwards or sideways: The same as above, but with a greater degree of the latter unless the writers are Totally Radical.
 * They're also used by, y'know, baseball players.
 * Bearskins, those tall, fuzzy headdresses, say British Royal Guards. Expect wearers to be stern and diligent, or uncomfortable wearing a cat on their heads if played for humor.
 * Berets say military, French or both. Also for artists and beatniks, and Jamie Hyneman.
 * Bicornes (two-cornered cocked hats) say "I'm fighting Napoleon!" or "I'm a Pirate-hunting Admiral in Queen Victoria's Navy!" But despite what the paintings would have you believe, these hats were usually carried rather than worn, which is why the French name for them is "chapeau bras", or "arm hat".
 * A straw Boater (or "Skimmer"), with flat crown and brim, says "barbershop quartet member" or "Venetian gondolier" (it's called a boater for a reason). Accessorize with a brightly colored blazer or striped shirt, respectively. If you actually wear one, it's the summer equivalent to the homburg. In the early twentieth century, associated particularly with the U.S.A. Worn by butchers in England, with bow tie, striped shirt, and apron.
 * Bowler/Derby: Was once the headgear of choice for the hardworking English businessman or government minister, but now is usually worn only for comic effect. For a comedic but classical look, go for a Bowler Hat. Characters who wear them are usually good humored, tricky, and/or odd/quirky, but still have an air of class about them, but bowlers are also often used for completely comedic characters as well. A green bowler is used occasionally as the Irish hat of choice.
 * In The Wild West, the man wearing the derby is a City Slicker Easterner who's either completely out of his element or looking to take people's money. Or both.
 * In Victorian London through Gangsterland, the helmet-like characteristics of the bowler (designed for riders, as the previously popular top hats, unlike the bowler, were easily knocked off by branches, could not survive being trod on by a horse, and offered no protection for a falling rider), made it incredibly popular among those who expect blows to the head. They can usually be identified by their low quality suits, slightly oversized hats, and face that demonstrates that the bowler only protected the top of the head (one very violent gang was called the "plug uglies").
 * Note the recent Bradford and Bingley ads with a woman wearing a bowler.
 * Bucket hat: A must for any fishing trip. Bonus points if there are fishing lures stuck into the crown for easy access. Used constantly instead of just for fishing, this style of hat can become an iconic part of the character. For example, Gilligan or Kisuke Urahara. Or Hunter S. Thompson (when he's not sporting his natural crown). But not Buckethead.
 * Given that the bucket hat was invented by and is still used by the IDF, the bucket hat has national associations in certain regional medias and military contexts (although the US navy wears a very similar hat). A slightly more conical and narrow-brimmed version, the kova tembel (lit. "stupid hat"), is always worn by Israel's national personification, Srulik.
 * A budenovka (a kind of kepi with a pointed top) says Russian Civil War, particularly the Reds (the Whites went for the garden variety peaked cap). But some time before, in the days of the Cold War, it could mean just Russia, just like the ear-flap cap.
 * Campaign Hat: In the modern era, most commonly associated with Drill Instructors (more likely than not played by R. Lee Ermey). Also associated with Boy Scouts, Mounties in their dress uniforms (which are their only uniforms in fiction), Park Rangers, and Smokey the Bear.
 * Connotation of wearing this hat is that the character is disciplined to a fault and will happily but angrily inflict that discipline on anyone and everyone in the vicinity who does not meet the organization's standards. Such infliction is a hair's breadth away from Large Ham status, missing the mark solely for lack of showmanship. A hat of this type atop a female's head is a very strong indication of a Tsundere tsuntsun personality type, with no Tsundere deredere in sight, unless one of the trainees is in danger.
 * Capotain, aka pilgrim hat (a traffic cone-shaped black hat, sometimes with a buckle): 16th- or 17th-century Puritan.
 * A chef hat (more properly, toque blanche) means you know your way around the kitchen, and you've got the credentials to prove it. Your record for serving up culinary masterpieces is as spotless as your white tunic. What's that, you say? Your apron is covered in grease and sweat stains? Then you're probably a short-order cook serving up concoctions best avoided by the living. But at the very least, your hat shows that you're the boss in this here kitchen.
 * Cloche Hat: You're a flapper. Or at least a young woman in the Roaring Twenties.
 * Conical straw hats: Peasants in southeast Asia or China (leading to the formerly-prevalent term "Coolie hat"). Like the fez, a generic foreign hat and mostly used in jest these days, unless the wearer is a Buddhist monk or religious pilgrim. Often worn by Ronin but likely discarded at the start of their first on-screen fight.
 * Gondoliers in The Elder Scrolls III: Morrowind wear these for some reason. Possibly easier to program than a boater?
 * Coonskin cap: A roundish fur hat with a raccoon tail dangling from the back. While versions actually were worn in pioneer days, it was the Disney Davy Crockett television series which made it into a pop-culture symbol equaling "old-timey Mountain Man/frontier trapper." Thanks to the Crockett craze, having a kid wearing one of these establishes a setting as "1950's America."
 * Cowboy hat: in the The Western, everyone important, color coded. In the modern era, Texans, or cowboy wannabes in any other state. Or even actual cowboys. Usually the sides are "rolled" upwards. Modern joke says this is so 3 cowboys can sit in the cab of a pickup truck (with no back seat). If only one side of the hat is rolled or one side is pinned, it's probably not a cowboy hat, but rather a slouch hat (worn by a jackaroo instead of a buckaroo).
 * Sometimes referred to as a Stetson, though that's strictly the name of an American company that also produces other kinds of hats.
 * Prominent amongst Mexicans and Mexican Americans as a sign of their ranchero roots. Suberte.
 * The deerstalker is a tweed cap with a brim in both the front and the back, and earflaps that tie together over the crown. Despite its name, however, almost the only person who will ever get to wear this hat is Sherlock Holmes. (Actual deer hunters should wear a proper hunting cap, lest they stumble across the scene of a murder and be called upon to use their supposed deductive abilities.) Nevertheless, be advised: if you absolutely must write Holmes fanfiction, at least display some common fashion-sense and only let the good detective wear it when he's out in the countryside. (It looks good paired with an Inverness coat.)
 * Fedora: An essential for any hardnosed Private Detective or mafioso, the Fedora is a symbol of the noir era. Characters who wear Fedoras on the good guy side are usually investigative, gruff, sneaky, while the bad guys wear loud, double-breasted suits, and are prone to Delusions of Eloquence. Outside the city, a popular accessory for the Adventurer Archaeologist. Not used too much nowadays, except as a Homage to the old days.
 * The Fez (or "Tarboosh" in parts of the Middle East), a stock foreign hat tells the audience that you're somewhere from the east. (Which is odd, because the city Fez, which named the hat, is in north Africa.) It doesn't matter where—it could be anywhere except Japan. This hat is almost always used for the Stock Foreigner, but nowadays the trope is so dead that it's squarely in the parody zone. Except on Shriners. Or the Doctor.
 * Flat caps (also called ivy caps) say "honest, working man" from Victorian London to The Fifties (and beyond, when they say "honest, working man who grew up in The Fifties or earlier"). Particularly common Oop North and in Oireland, where they're invariably made of tweed. (In the U.S., they mostly say "cab driver" or "hipster college student".) They could also mean Brian Johnson. Their other (now archaic) meaning is that the wearer works at a golf-course as a caddy.
 * A hairnet means your job sucks. The cool people in food service get chef hats. Worn as a fashion, it's called a snood, which is hilarious.
 * See also the goofy hats of Burger Fool.
 * Plastic hard hat: an engineer or construction worker.
 * With a light attached to the front: a miner or a spelunker.
 * Hennin: The modern name for a tall, cone-shaped hat (See Pointy Hat, below) like a Wizard Hat, only with a more or less elaborate veil attatched to the top. Universally associated with ladies in The Middle Ages, though actually worn only for about 50 years at the end of The Late Middle Ages.
 * Homburg: A stiff felt hat that strikes a nice balance between the staid (and silly-looking) bowler and the softer Trilby and Fedora. Has a hard, curled brim like the bowler, but a lengthwise crease in the crown like the latter two (though usually not pinched in front). A common sight on the head of mid-20th-century politicians such as Winston Churchill, Konrad Adenauer, and Anthony Eden, it has also come to be identified with The Mafia, leading to the nickname "Godfather hat" in some circles. Usable in settings from The Edwardian Era onwards (it became popular after Edward himself copied the hunting-hat of his least-favourite nephew, Kaiser Wilhelm II), the Homburg projects class without being as ostentatious as a top hat or as silly as a bowler. For this reason, it's still the hat of choice to go with a tuxedo. Interestingly, Russian-turned-American (he fled during the Bolshevik Revolution) helicopter pioneer Igor Sikorsky for the most part refused to be caught dead anywhere without wearing a black Homburg hat, even while test-piloting his own prototypes for their first EVER flights
 * Hunting cap: A thick, flannel (and often fur-lined) cap that resembles a baseball cap, but with earflaps that can be tied over the crown when not in use. Usually seen in bright-colored plaids, which help them stand out in the woods where there can be multiple people with guns ready to shoot at even the slightest hint of movement. As the name suggests, it is best suited to hunters dressed in an incongruous combination of camouflage fatigues and a safety-orange vest. (A deerstalker with matching Inverness coat is a great way to get mistaken for a deer and end up strapped to the hood of someone's car.)
 * Those of a literary bent, however, might associate it with a certain medievalist buffoon from New Orleans.
 * Jester Hat: A violently-colored hat with three (originally two, representing ass's ears) large floppy points, often tipped with bells, occasionally topped with a cock's-comb. When worn in Real Life it screams "I'm a fool!"(or "I'm a stoner!") but may denote Obfuscating Stupidity.
 * The Kepi is a must for any self-respecting gendarme or member of the French Foreign Legion. Charles de Gaulle managed to be seen in one and still be taken seriously, but they tend to be given over to parody nowadays. (See, for example, the Steve Martin incarnation of The Pink Panther.) A soft form of kepi called a "forage cap" is also associated with the American Civil War.
 * Kabuto: No self-respecting Samurai would go into battle without one. Ornamentation can range from the strictly utilitarian to the ridiculously unwieldy, depending on social status and time period. In works without samurai, similar headwear can be seen on Humongous Mecha, and The Dragon to Fascist villains In Space. (If the Mooks are wearing a Stahlhelm, it's a fair bet that The Dragon will have a kabuto or something similar.)
 * Kerchief: Worn on top of the head going back from the hairline and tied under the chin or at the nape of the neck indicates a working woman, farm girl, or other female doing manual labor. If in more villainous or anti-heroic hands, then they are worn (often covering the mouth and/or nose) by thieves and bandits.
 * RED kerchief tied under the chin (1920s Russia): this woman is a commissar, a chekist or otherwise aligned with Bolshevism.
 * Kerchief tied under the nose: old-timey Japanese burglar. Looks as ridiculous as it sounds.
 * Metal helmets in general: a warrior, ranging from a modern soldier to a medieval/fantasy berserker.
 * With horns: a Viking or an opera singer. (Although neither real Vikings nor real opera singers ever wore them.)
 * With wings: a Valkyrie or an opera singer playing a Valkyrie, or a Celtic warrior. Or a dragoon.
 * With a crest: an officer in an ancient Roman or Greek army, or in a fantasy setting based on those cultures.
 * With a visor and a plume: a Medieval knight.
 * Miters (or Mitres for Commonwealthers and pretentious Americans) are those hats now usually shaped like spades or Gothic arches, symbolizing bishops and abbots (less commonly, abbessess) in Anglican, Eastern Orthodox, Eastern Catholic, some Lutheran, Oriental Orthodox, and Roman Catholic Churches. (Formerly the hat was worn with the "horns" on both sides, but somewhere around 1100 it was turned sideways, giving the version familiar today. The original sideways version can be seen in the Imperial Crown of Austria.)
 * A mortarboard says, "I'm graduating!" But don't assume that academic dress is the same everywhere. Do your homework.
 * The Newsboy Cap is similar to the flat cap, but with a longer brim and a poofier crown whose pieces come to a single point on top. As the name suggests, it says "turn-of-the-century newspaper-seller", or occasionally, "golfer wearing too much plaid".
 * Panama hats (made of straw with a very fine weave) in any significant number mean you're somewhere in the tropics. Or you want to be. Or you're Hannibal Lecter or Charlie Chan. Can be combined with a Hawaiian shirt or light-colored suit for extra effect. In British works, stereotypical headgear for The Vicar.
 * And if its trim is turned down, it's probably Santos Dumont. Or an impersonator.
 * The peaked cap has several related meanings, according to the Hollywood Dress Code.
 * Dark brown, blue or black says military or police. Usually has minimal amounts of "scrambled eggs": decorative gold-colored cords on various areas. White variations either imply police in tropical areas or officers in US/Commonwealth navies.
 * The more flat peaked cap in one of these colors, or in white, suggests the wearer could be in a non-military occupation such as a commercial airline pilot.
 * The larger, higher peaked cap (in a rather consistent shade of khaki throughout all points south of the Rio Grande) says Banana Republic military or police. This is where the scrambled eggs get piled on as much as possible.
 * The largest, black-and-silver peaked cap is Putting on the Reich. Notably free of scrambled eggs.
 * And someone wearing a black leather peaked cap is either a Red Commissar (if the cap has a Soviet badge) or a big fan of BDSM (if it doesn't).
 * The Pickelhaube is clearly Prussia.
 * The connotations of a character wearing such a helmet includes some (but rarely all) of the following traits: honorable, ruthless, tactically astute, arrogant, gentlemanly, sexist, power-hungry, merciless about the tiniest details and inhumanly self-disciplined. Frequently accessorized with a monocle and a Dueling Scar. Examples include Coach Oleander from Psychonauts (complete with a cork on the tip of the spike for safety).
 * Pith helmets carry the connotations of the Adventure Archaeologist, Egomaniac Hunter, Gentleman Adventurer, etc. Generally worn in either on a safari in the Savannah or in the desert (if it's the latter, you could also be a World War I/II soldier keeping away Those Wacky Nazis and/or their Italian allies).
 * Pointy hats are synonymous with wizards and witches, especially but not only on Discworld. A stereotypical witch hat will be plain black with a brim, while a wizard's will often lack the brim and be decorated with magical and/or astrological symbols.
 * Very much on the other hand, if you're wearing one of these along with a dopey expression, and you are sitting in a corner, it becomes a "dunce-cap", indicating extreme academical failure.
 * The pork pie hat is similar to a trilby or a fedora but has a flat top. It's often associated with jazz musicians and similar artist types. Several Hanna-Barbera characters including Huckleberry Hound, Yogi Bear, Top Cat, and Hokey Wolf wore this headgear. In real-life, the most famous wearers of this type of hat included Manhattan Project physicist J. Robert Oppenheimer, singer/comedian Dean Martin, silent-film slapstick legend Buster Keaton, and notorious architect Frank Lloyd Wright.
 * Propeller beanie: a Nerd or Geek. Was also a popular form of hazing for college freshmen, back in the day. The propeller doesn't actually allow you to fly unless you're Doraemon.
 * A slouch hat (heavy felt hat with a brim that can be pinned to the crown on one side) says, "I'm in the cavalry!" Or, "I'm in the Outback, mate!" (Or both.) Often called an "Akubra", though this is strictly the name of an Australian company that also makes other kinds of hats (including a facsimile of the one worn by a certain Adventurer Archaeologist).
 * Sometimes worn by Pierre Trudeau.
 * A sombrero says Mexican outlaw (often from the Old West era). Commonly found South of the Border, as well as in Spexico. A smaller, flat topped version, called the sombrero cordobés or gaucho hat, is closely associated with Zorro and other Spanish-speaking aristocrats.
 * The Stahlhelm, used in Nazi Germany, is a popular look for Mooks working for the Fascist-esque bad guys. See, for example, the Galactic Empire or Prinicpality of Zeon. Note most post-WW2 helmets (Including the US helmet designs the PASGT, MICH and LWH) use its cut.
 * Sun hat is a broad label applied to many types of wide-brimmed hats designed to, yes, protect the wearer from the sun. Overlaps with the Panama, but are usually made of cloth, and with a wider brim than a bucket hat. A woman in a particularly big and floppy one, carrying a trowel or similar tool, equals "hardcore gardening enthusiast." Paired instead with a long flowing dress, she becomes a fashion-plate/trophy wife, or something far more sinister. A older heavyset man wearing a large, gaudy and/or tasteless sunhat can again be shorthand for "tourist, American, obnoxious." "Sun hat" may also refer to summer hats, which are generally straw alternatives to felt hats (the boater is a top hat or homburg, a panama is a bowler or fedora, and a stetson is a show of poor taste).
 * A sun visor means that you're a preppie if it's all one color and you're female, a wanna-be beach god if it's all one color and you're male, or an accountant / bank teller / counterfeiter / card shark (depending on the genre) if it's a fabric band with a translucent green bill.
 * A Tam O'Shanter screams "I'm from Bonnie Scotland!" just as effectively as wearing a kilt or playing bagpipes.
 * Tinfoil hats are the only real hat anyone needs. Wait, why are you looking me like that? The metal helps keep out the mind-control waves used by the government. And sometimes the aliens. You know they're working together, right? Always watching what we're doing, what we're eating... who knows what they're really planning, but you have to be prepared. I've got an emergency supply of 12 rolls in my kitchen, just in case the Feds try to move in and cut off our source of protection. Note that, unlike other hats, these should never be removed at any time, unless you want them to come for you. Those of us who know the truth about the Kennedy assassination, the moon landing, and that mysterious cabal controlling the world's governments must do everything we can not to be caught.
 * Ironically, the tinfoil would likely act as some sort of antenna amplifying the alleged mind-control signals or otherwise serving as a lens to make it easier for the monitoring equipment to read one's mind, so this hat would do the opposite of what the wearer wants.
 * Top Hat: An old way to tell if someone (most often, but not always a male) is rich. With overly/stereotypically wealthy garb, the Top Hat is a must. Originally made of glossy beaver fur, later generally of silk. (The black wool ones popular with people like David Beckham are for undertakers.) Light grey felt is another, slightly less formal option for daytime wear. Like the monocle, you'll never see this one unless someone being parodied, or unless there's an old style magician or mustache-twirling movie-serial villain in the crowd. (Technically, it's still the proper headwear for use with a morning coat, frock coat, or white-tie-and-tails, but these, too, appear virtually only in parody nowadays, so that anyone wearing the top hat is doing so improperly as a display of wealth, hence the image of the hat). It goes with the Uncle Pennybags image. Noteworthy in that it is sufficiently iconic that [[media:awesomemonocle.jpg|sticking one on top of a Smiley Face]] is enough for most observers to consider the resulting character as a wealthy male. The opera hat is a variant with a collapsible crown (originally meant for convenient storage while at the opera), which is good for magic tricks. A battered top hat (possibly with the crown mostly detached and sticking up like a tin lid) is the headgear of choice for Victorian tramps.
 * Example: On The Daily Show, John Oliver occasionally wears a top hat, monocle, and tuxedo when he has to look demonstratively British.
 * This hat gets a lot of variation when worn by the Millennium Earl. Who just so happens to be a caricature of a Victorian Gentleman. Except he is very sinister.
 * Tricornes (three-cornered cocked hats) are for pirates, swashbucklers, highwaymen, and Frederick the Great. Also a prerequisite for the American Revolution.
 * Depends how you wear it: Point out means patriot, while point in means pirate.
 * The Trilby looks like a Fedora, but has a lower crown and shorter "stingy" brim (though hat experts will get into heated arguments over where the dividing line between the two is, precisely). It was often used in older stories for reporters, usually with a "PRESS" tag tucked into the band. Also, A Clockwork Orange. Or Trilby, or his writer. Also a favorite of jazz musicians and hipsters. If made of sewn fabric instead of moulded felt, expect a Grumpy Old Man in a suit that was obviously bought when he was several decades younger (and several inches taller). Please note that many people who rail against fedoras on the grounds that they look silly are actually thinking of trilbys. A good way to tell the difference: Bogie wore a fedora. Bing Crosby wore a trilby.
 * A Tudor bonnet means that you're in England during the Renaissance (specifically, the reign of the Tudors), or any play by William Shakespeare, regardless of when and where it's set. If you're in the modern day, you're probably at a university, and know far too much about far too little. You might occasionally pass on some of that knowledge in between grading papers and furthering that in-depth mastery of your sub-sub-sub-field.
 * Knit wool hats (or, as some people call them, toques) indicate it's bloody cold. Or you're a skater/punk, but only from the '90s.
 * Turban: Another stock foreign hat, it's another 'somewhere from the East' cap, though in this case, it's more specific: either the Middle East or India. Wearers in fiction often occupy an important but ultimately stereotypical/bit role; if your average superspy is in India looking for his contact, he'll be the guy wearing the turban. Another trope so dead it's only parodied outside of very specific regional variations used to denote setting.
 * Exceptions being made for Sikhs, but how many Sikhs have you seen lately on TV or films?
 * An episode of Only Fools and Horses featured a Sikh doctor who inspired Del Boy to invent the "crash turban", a self-explanatory device which has to be seen to be believed.
 * A fortune-teller or mentalist might sport a particularly gaudy version.
 * If made of satin and lightly wrapped to closely follow the contours of the head, indicates cutting-edge 1920s feminine fashion.
 * A Tyrolean cap says "dedicated hiker", or, when paired with lederhosen and suspenders, "yodeler".
 * An ushanka (a fur hat with ear flaps) says Russia (Wikipedia has "Russian hat" as a redirect, try to find another country with a similar redirect). If there's a Soviet badge on, Reds with Rockets. It's common to want to touch a hat that sexy.
 * Curiously, a hat with a very similar design, but worn with the ear flaps down, has a completely different connotation.
 * In Russia, the ushanka with flaps down says bum or rustic old fart.
 * It also seems to be popular in Canada and the northern United States when it's really cold outside. (Think Fargo.)
 * A red, checkered cap with ear flaps and a wool lining means you're a lumberjack, and possibly that you're okay.
 * Whoopee cap: A felt cap with a short brim turned up all around, cut into a jagged shape reminiscent of a crown. It's usually accessorized with pins and buttons with slogans on them. Popular among kids during the 1930s and 1940s, when they would cut up their fathers' old (and, one hopes, officially thrown-out) fedoras to make them. Most appearances in fiction died out after the 1950s, but it can be seen on characters like Jughead and Goober Pyle. The stereotypes for wearers (if they're not kids in contemporary works) are "teenage Delinquent" or "Man Child", depending on age.
 * The yarmulke (also called a kippah) screams "I'm Jewish!" at the top of its lungs. But it's only worn by men, and hardly ever worn outside of a synagogue by non-Orthodox Jews. Only use if you need to make someone visibly Jewish without resorting to racial stereotypes.
 * Oddly, wearing one of these (called a "zucchetto" in this context) could also mean you're the Pope or other Catholic clergy, depending on the colour. Possibly they took up the fashion to keep their tonsured heads warm.
 * Similarly, a black fedora or a shtreimel (which looks like a big fur hockey puck), combined with curlicue sideburns and a beard, takes the Judaism Up to Eleven. (In Real Life, people who wear hats like these are part of a specific ultra-orthodox subsect called Hasidism. Don't expect the average writer to understand this, however.)
 * Incidentally, in Medieval Europe the traditional Jewish hat was quite different-looking: a pointed cap with a narrow brim. See here.
 * The 19th century had a wide variety of hats and helmets, associated with different branches of the military: the Busby, the Czapka, the grenadiers' miter-cap, the Moretto, the Papakhi, the Shako, etc. Nowadays, you are most likely to see any of these on a marching band. Except papakhi, which is still worn by Cossacks, native peoples of Caucasus and Russian colonels and generals.