"In true Western tradition, your level of badassness is dictated by the size of your hat: Ray and Thomas both wear big hats and therefore eat danger and shit bullets, Wee-Um doesn't get a hat so the best he can hope for is to eat Weetabix and shit healthily."
Warhammer Online has the Knights of the Blazing Sun, an elite army of wandering warrior monks who worship Myrmidia, goddess of warfare and civilization. They are commonly seen running around with golden helmets pimped out in gigantic feathers painted any variety of colors, ranging from red, to blue, to gold. Some of them may simply forego the feathers and have a gold statue of a falcon perched on their heads.
Hat wearers are a bit of rarity in the Disgaea series, but almost all of them have nice hats. Some examples include the Gunner class, Salvatore, and most recently, Fuka.
The Dynasty Warriors game series features a number of memorably bizarre hats taken from the Three Kingdoms era of China, most notably the Propeller Hat, which is Truth in Television.
Lu Xun's hat is particularly bizarre, up until the character design changes in the 6thgame. Fans have often taken the liberty of making fun of his hat in fanfiction.
Sun Quan's Propeller Hat looks like a thin piece of cardboard stuck to a sardine tin strapped to his head. Sun Quan wears a particular ostentatious version due to naming himself the King of Wu.
Sima Yi's headgear gets crazier with each installment. It's anyone's guess what he hides under the thing.
Lu Bu, the period's biggest badass, makes his presence known with a tiny cap sporting two enormous feathers that reach down to his feet. Only a real man could pull that off. In Chinese Opera, feathers denote a battle role.
Kessen II also takes place during the Three Kingdoms period and features some pretty redonkulous hats. Of particular note is Zhang Liao's antler helmet and Sun Quan's eagle hat.
The original game is in love with this trope, to the point where the rank of any given general can be inferred from the scale and elaborateness of his hat. Some of the most memorable include the enormous clan-crest of Tokugawa Ieyasu, the dragon-head helmet of Ukita Hideie, the Viking-esque horns of the Badass Beard Fukushima Masanori and, of course, Date Masamune's famous crescent-crest. The handful of exceptions become just as memorable by their inversion of this otherwise ubiquitous trope, particularly the Badass Mask-wearing Chosokabe Morichika and Badass Monk Ankokuji Ekei. As noted below, this is a pretty popular trope for this period of Japanese history.
Games set in the Sengoku era of Japan, such as Samurai Warriors and Sengoku Basara, also feature some pretty spectacular hats. There's Date Masamune's crescent helmet, Honda Tadakatsu's deer antler helmet, and Naoe Kanetsugu's helmet which is engraved with the kanji of "love." Mitsunari's ridiculous hat looks like he turned a sheepdog into a hat. Tokugawa Ieyasu's crazy tall hat, provoking Takeda Shingen to make the remark, "Ieyasu has two things that exceed his own worth, that warrior, Tadakatsu, and that ridiculous hat of his." Also Azai Nagamasa's helmet/hat.
Mouri Motonari's giant green "okra" hat deserves an honourable mention. His alternate hats are even more impressive, and his "chameleon" hat in the third game blows them all out of the water.
And the really funny thing is that most of those helmets, such as Masamune's, Tadakatsu's or Kanetsugu's? Were real. Nothing beats Date Shigezane, though, whose helmet was adorned by a bloody huge, golden centipede.
And the H-Game parody Sengoku Rance continues this proud tradition, and Uesegi Kenshin is the owner of a triangular hat that not looks nice, she uses it like a lance point while charging the enemy!
Mario, of course, has his iconic red cap with an "M" on it. It spawned out of the difficulty to draw hair on a sprite back in '81, so he was instead given a cap. Similar situations also spawned his equally iconic overalls and his moustache.
Luigi has a matching green one. (With an "L", naturally.)
Super Mario 64 has several nice hats, including the Wing Cap to fly, the Vanish Cap that makes Mario invisible and the Metal Cap that makes him become metallic. Also, when an enemy takes off Mario's own hat in a desert level, he takes damage from the heat. Noticeably, in any level, being hit by an enemy while hatless will make you take one Hit Point more damage than you would with the hat. Apparently Mario's hat projects its own forcefield.
In the remake of this game for the DS, picking up a playable character's hat (Mario, Luigi, or Wario) will turn you into that character. If you started the level as one of these characters and lose your original hat, hitting a Power Flower block will unleash an angry Bob-omb rather than the helpful flower.
In Super Mario Sunshine, Mario's health slowly drains if an enemy steals his hat. Apparently the stress of losing his hat weakens him, although, given that he's in the tropics, this is kinda understandable. Sunburns hurt!
Lechku and Nechku in Ōkami pull random objects out of their hats as attacks. Waka also has a pretty bitchin' hat which never comes off until he thoroughly gets his ass whooped by Yami. Orochi has eight giant, brightly colored Nice Hats that denote the element they rule over.
Some other characters in Okami also have some wacky headgear. Queen Himiko's hat is on fire while her husband, the Emperor, has a Miniature Treasure Boat for an hat. Mr. Flower, a Sei-An Citizen, has a Bonsai Sakura tree which seems to be merged with his skull. Kushi packed some Rice bales on her head. Madame Fawn, the fortune-teller, has a deer skull with some Ofuda on her head. Mika, a Shinto Priest, has a miniature building on his head. Yatsu, the (deceased) priest of the Gale Shrine, has a Miniature Windmill on his head. Orihime and King Wada A.K.A. The Water Dragon both seems to have containers on their head, the Dragon Palace guards have underwater flora or coral on their heads. Most if not all the Poncles have some kind of insect in guise of a hat. Nami has a bucket of Sake with an arrow embedded to it and Mushi's Mama has a Water Vase on her head at all times. Whew!
In Overlord, the player's impish minions have a fondness for nice hats, and will fashion them out of just about anything if they can't find a real one - gold or iron helmets, hoods, flowers, pumpkins, bits of dead enemies ... you name it, one of them will gleefully stick it on his head. The Overlord himself, of course, never, ever removes his helmet, although the player can upgrade it several times.
The most extreme example has to be in the sequel where one minion will make a hat out of the top of a Aquila which is golden and almost as tall as he is.
I-No in Guilty Gear has a living hat that looks like the Sorting Hat'sEvil Twin. Johnny and May naturally have some pretty sweet hats, too, being pirates. Johnny's is an homage to Johnny Cash.
Kirby has tons of hats, one for (almost) each of his powers. He should have his own haberdashery. Particular examples include the headdresses he gets for Fire, Ice and Plasma, the jester cap he has for Beam (and the shiny one for Mirror), Link's cap with a tassel for Sword, and the reversed ball cap he has for Yoyo.
Despite this, when Red Mage was dead/incapacitated Black Mage started wearing his hat on top of his own. Presumably as a trophy. Of course, Red Mage (on fire) is a nice hat...
In Final Fantasy XI the NPC Maat tests your fighting ability in your job to advance from 70 to 75. Beating Maat in all fifteen of the original and advanced jobs (To A and Wot G not included) nets the player a special scene with Maat's story and the reward of his iconic beret. A challenge less than .5% of all 500k+ players have completed.
All of the caster classes of Final Fantasy Tactics (save the Calculators) have a Nice Hat: Black Mages have a Robe and Wizard Hat, White Mages are In the Hood, Time Mages have a pointy pope-esque hat, and Summoners have positively Freudian headbands; furthermore, the Mediator's hat looks like a pillow, and the Lancers have some pretty sweet helmets evocative of dragon's heads.
In Metal Gear Solid 3, Ocelot is rather fond of his hat. During his duel with Naked Snake, Snake's allies actually suggest shooting off Ocelot's hat as a tactic.
Though it does not look very impressive, Naked Snake's Martial Arts Headband is still an impressive piece of headgear. Shortly after the beginning, on a covert operation within enemy territory, his Mother Mentor, Blood Sister, and best friend Boss betrays Snake and joins the Big Bad, who orders her to kill him. After having the crap beaten out of him, she throws him from a bridge into the river below and in a last desperate try to catch himself, his hand only gets a hold on her bandana. He narrowly survives and returns with the mission to stop the Big Bad and kill her, wearing the very same bandana...
Also, after becoming Big Boss, Naked Snake starts wearing a military beret. It makes him resemble Che Guevara with an eyepatch, which is even pointed out during Peace Walker.
Solid Snake has his a bandana of his very own, and sometimes it gives him infinite ammo.
Chancellor Cole from The Legend of Zelda: Spirit Tracks wears two green top hats on top of his head, side by side. He has a horn underneath each, explaining how he's able to wear two hats as he does in the first place.
While Touhou may be a universe of Nice Hats, Keine Kamishirasawa stands out. She wears what can only be described as a miniature pagoda on her head, in her human form.
A minor meme among the fandom: "If a Touhou loses her hat, she will certainly die."
You can equip hats in The World Ends With You, and you eventually get Minamimoto's cap as an item. It gives you more stat boosts than most good items do in one stat, in all three stats.
In Soul Calibur IV, Talim gets her own Nice Hat as part of her costume's redesign for the game. The Character Creation and customization modes have a bunch of them, so you can give them to just about anybody.
She also has one in her third costume in Soul Calibur II
Most of the named characters in Archaic Sealed Heat (and some of the generic units) that don't have amazing hats have ridiculous hair instead. Some of them have both at once. Now add goggles and eyepatches to the mix, and things just get awesome.
Maximillian's cap(s) in Dark Cloud 2 are probably the only thing that differentiates him from other standard RPG heroes appearance-wise. And they're neat looking, to say the least.
Made a Nice Hat even moreso because he will wear the cap when wearing nothing else, seriously.
The sequel suggests there may be good reason for it - one demon negotiation branch suggests he's covering something important up.
Bishop Sarasai from the Suikoden series wore a stunning example that was almost bigger than he was. Many tears were shed when he abandoned it for the third installment. In the same game, Yuber wore a rather stylish hat himself. Whether this makes up for the loss of Sasarai's is up for debate.
A recently-added quest to World of Warcraft involves meeting up with an old guy with a nice sombrero hat. Turns out that this old man used to be quite the fighter back in the day, and many would challenge him to a fight for said hat. Naturally, you can go back in time, find the younger version of the man, and beat him up in order to receive the hat as a reward (as well as another hat in the Heroic version of the dungeon, which summons the ghost of the man's coyote companion whom you killed to beat him). The quest name? Nice Hat...
There are also other hats which are worn just for their looks, including a pirate hat (which summons a matching parrot) that is incredibly hard to obtain. Another special case is a quest reward hat that you can reach into for a random beverage.
When Cataclysm (re)introduced the Gilneans as Victorian-era British, they naturally got top hats (and every worgen gets one as part of the starting quest progression). There is also an even fancier version (the aptly named High Society Top Hat) craftable by tailors.
Ragnarok Online' has an awesome variety of Nice Headgears, and the players are obsessed with getting the nicer ones. Since they are the only noticeable change to player sprites, the obsession is pretty much justified.
Some Nice Hats do give Nice Bonuses to some classes.
Yuri's black hat is the nicest because it gives +10 badass to an already badass character.
In Fat Princess, you pick your character class by putting on the appropriate hat.
Joshua's hat in Fire Emblem 8. There is also a ROM hack featuring Gheb and it includes Joshua and his hat. The coolness of his hat is taken to such ridiculous extremes that it is treated as a living being and lord help anyone who insults his hat.
Isamu's newsboy-style hat in Shin Megami Tensei III: Nocturne practically became its own character in fan art and 4Koma comics. Even his "God" wears the damn hat.
In Guild Wars, the ritualist class can get an extremely nice hat◊, though it is one of the most expensive items in the game and to get it you need to enter the Bonus Levelof Hell.
Inverted somewhat in Mega Man 9, where you can spend the game's currency for the privilege of playing as Mega Man without his trademark headgear.
However, Mega Man takes double damage when he's not wearing his helmet. Some Mega Man games have helmets of the character you are using as one up items. In Mega Man And Bass, the game over screen shows your character's helmet on the ground.
Meanwhile, in the Mega Man X series, the hero can always find additional upgrades to his helmet that has extra functionality and generally is part of a collectible series of items to unlock some sort of super awesome secret.
Mega Man 10 instead gives us the Wily Machine's awesome pirate hat.
The male player character Brendan in Pokemon Ruby/Sapphire/Emerald has a hat so nice that it's practically indistinguishable from hair.
After years of debate, the games' artist Ken Sugimori finally confirmed via Twitter that it's a knit hat.
Wes and Michael, however, are an exception. The closest you'll get are Wes's flash goggles and Michael's Aura Reader.
Leaf's and Red's Nice Hats are so nice that you'll rarely hear from them without their originals.
Pfft, N from Black and White scoffs at your law. He and the protagonists have nice trucker caps.
Outside of Gen III, Bianca is the only rival who has one.
According to Chuggaaconroy, the trainer with the dumbest hat in the land is bound to succeed.
Actually, the only protagonists not wearing any headwear are Kate and Kellyn of Pokémon Ranger: Shadows of Almia.
That's the reason why only one of them can appear in-game. Having two hatless protagonists would make the game explode. Although, Kate does have earrings.
Fallout 3 has the Pre-war Hat, which is a spiffy fedora. Aside from looking nifty, it gives a bonus to Perception, making you shoot better. The downside is that it's rather fragile, and doesn't give much protection. But it's worth it for a killer hat. There's also the "Shady Hat" which not only increases your Perception, but your Sneaking ability as well.
Fallout 3 has so many nice hats it's a pity the player is restricted to one at a time. Further examples include Euology Jones' Pimp Hat, a 18th Century style wig, and Abraham Lincoln's stovepipe hat, which is just made for wearing while mowing down the slavers of Paradise Falls. Or the incredibly rare and hard to find Chinese Commando Hat, wear with a Duster of any kind and you can pretend to be a Soviet conscript!
The "Chinese Stealth Suit" from the Operation: Anchorage add-on has a fun but overpowering glitch, where wearing it allows you to wear as many hats as you please. With the right hats, one can almost completely max out on all of the player's stats.
The Stormchaser hat is particularly awesome. It's a white fedora, complete with goggles, and is worn over a hood. It looks especially awesome when worn with the T-51b Winterized Power Helmet, utilising the above glitch.
Fallout New Vegas also has it's share of Nice Hats. 1st Recon members all have a red beret as a symbol of their Badassery (it gives the player a big boost in crit chance). Cass wears a nice cowboy hat. General Oliver's hat is far more impressive than the man whose head it rests upon, covered in gold stars and a golden NCR sigil.
Dermot, a former prospector in Westside, wears a spiffy police hat. Since he and his partners are actually slavers of the worst sort and the quest to bring them to justice allows you to kill them yourself, you can thus claim it for yourself as you bring the law.
The REPCONN testing site has a fully intact space suit with bubble helmet, both of which are surprisingly good armor.
The power armor helmet and the Remnant armor helmet.
The Legion provides all sorts of nice headhear, from the Vexillarius wolf-head hood (with sunglasses) to the plumed Centurion helmets. As with everything the Centurions wear, it is made from equipment taken off their foes, in this case the headpiece of a super-mutant brute.
Wario Land 1 has different types of hats as the power ups, including a hat with horns which increases strength, a dragon hat which breathes fire (even underwater), and a jet cap which is pretty much a head mounted jet pack.
.hack, both original tetralogy and G.U., has some very nice hats. To name a few, Kite's big red hat with earflaps, Mistral's enormous hat, Elk's more moderate one, Marlo's bitchin' helmet, Endrance's rose-covered one, Sakubo's transforming hat (with one end curving up into a point, the other curving downwards,) Atoli and Shino's big poofy hats with tassels, and assorted hats on NPCs. Yeah. It's a Hat Series.
Fatal Fury/The King Of Fighters: Terry Bogard is almost always seen wearing an ordinary (but still rather nice) baseball cap. It never leaves his head until a fight ends. In the case of his Fatal Fury appearance, The Anime of the Game upgraded his cap to include a metal plate for no discernible reason at all. Still looks Badass, though.
Mortal Kombat 9's Test Your Luck mode may provide the Headless Kombat mode which has a major effect on Kung Lao. Without a head, he can't wear a hat and becomes unable to use half of his attacks.
Let's not forget Raiden and his iconic Conical Asian hat.
Most gun kills in Total Overdose cause the victim's hat to hover in the air briefly. Moving in to position your head beneath it at that time gives a 'Hat Catch' bonus plus extra points per kill while wearing it. There's also the 'Sombrero of Death', a Day-of-the-Dead costumed zombie in a sombrero, who packs a grenade launcher to fight for you.
Caffeine Nicotine out of Samurai Shodown 2 wears a nice-sized hat. When armed, he swings it as his weak slash/punch. When unarmed, he just swings it for all side moves. And if he does a dive roll, the hat itself is what's seen as rolling along its brim.
The Pilot's Helmet in Ratchet & Clank is intended simply as a plot MacGuffin letting you use certain aircraft. It is, however, possible to equip it on dry land. It makes Ratchet stop looking like a weasel and start looking like a hero.
Romancing Sa Ga: Minstrel Song features a lot of nice hats as part of The Remake giving the whole cast a makeover. Examples include Aisha's odd hair-wrappish thing (complete with twin braids hanging out the back in a way that leaves you wondering how she arranged it like that in the first place), Sif's Horny Vikings-invoking literal skull-cap, Hawke's puffy Pirate hat, and Diana's teensy crown that doubles at invoking Hair Decorations.
The male protagonist of Legend of Mana wears a big red floppy hat that gets complimented (and made fun of) on at least one occasion; for the female one, it's her kickin' rad hairpipes.
At one point, his hat is (for complicated reasons) causing extremely irritating problems for him and his apprentice Luke. When Luke logically suggests that the Professor take it off for a little while, though, the Professor flat-out refuses, since "a gentleman can never be seen without his hat."
Team Fortress 2, also known as The Quest For More Hats, or Hat Fortress 2. At the time of their introduction, there was a single hat for each class giving a total of 9 hats. There are now well over a hundred. Hats are Serious Business in the Team Fortress 2 world and the base broke several times over various updates due to hats. The game is now advertised as "The world’s #1 war-themed hat simulator"!
Almost?! They snuck hats into Portal 2 behind the Portal team's back!
They had to stop Robin Walker from putting hats in the latest Counter-Strike.
One update was "The Hatless Update", promising 100% non-hats. And a hat-like pin was secretly included by a mischievous programmer, a promotion for Portal 2.
People have also joked that this alone makes Team Fortress 2 a Spiritual Successor to RuneScape. A joke on Wikipedia where someone made an edit declaring the game to be about collecting party hats, known for its "The one with the most hats wins" rule.
Hats also function as a joking status symbol among players, since it takes quite a bit of time (through the random drop system) or money to attain one. The one exception is a hat called the Ghastly Gibus, initially attained through a hidden page in the Halloween Update, but now achievable by mercilessly slaughtering a player wearing one. Due how easy it is to get one, wearing it is considered a sure fire symbol of noobdomnote The exception to this exception is the "Ghastlier Gibus", an automatic upgrade that counts how many years ago you earned your Gibus.
In Simon the Sorcerer, Simon has a nice wizard hat which he uses to store his inventory. Including ten-feet-long ladder.
Maxwell from Scribblenauts wears a strange but neat red hat that has been dubbed the "rooster hat" by fans and its creators. The best part? In some countries, a real life version of this hat is available as a pre-order bonus!
In the game itself you can spawn a top hat, glue it to a unicycle, make a panda ride the unicycle, glue a saddle to the panda, and then make a wizard sit on the saddle.
The hat was in such high demand that it's now available at all US Toys-R-Us stores as a regular item.
If your family member general is insane in Rome Total War, they will often give odd (or rather, crazy) pre-battle speeches, such as:
"Although the Enemy have the Moon People on their side, we need not fear, for we have our lovely hats, and they shall protect us from their fearsome gaze!"
From Software's Evergrace features many nice hats, which are also quite beneficial since normal clothing works just like armor, just with less durability. Fear be-hatted catgirl Sharline, FEAR.
The sentient phases of Spore offer an increasing selection of clothes, including Nice Hats.
Diablo and Diablo II have the Harlequin Crest. The original has a drawback of -3 to your Armor class, but the +2 to all attributes is tempting.
In the sequel it is one of the best hats in the game. Unfortunately, it stands out like a sore thumb in a fairly realistic and gritty Grimdark world because it is a neon green hood.
In Demon's Souls there is a way to get a very nice, very large yellow hat by slaying another player in PvP while fighting as a storyline boss.
While the example above is more of a Turban than a hat, the legitimate Official's Cap is a very pimping fedora-esque hat. In a Dark Fantasy world. Not only it looks good, it is required for a sidequest to free a certain NPC. Yuria's Three-horned Hat definitely counts.
Dark Souls has Big Hat Logan and his very wide brimmed steeple hat. The hats the other Vinheim characters wear aren't too shabby either.
Another example is Pharis' Hat. On males, it's a narrow-brimmed Robin Hood-styled hat. Wear it while using Pharis' Black Bow and you too, can be the Fantasy Counterpart of Robin Hood! On females, it turns into a very sexy beret that matches well with the Leather Armor set. Other example include Beatrice's Witch Hat.
A few Eternal Sonata characters sport some nice/interesting hats. Fredric Chopin's feathered top hat is something of a trademark for him; the same feathers appear in one of his attacks.
Shades' pink baseball cap with little wings on the sides in Ufouria. It may be a Shout Out to Dr Slump, where Arale often sported a similar cap.
Henry Hatsworth In The Puzzling Adventure kicks off when the title character discovers a bowler hat that deages him by several decades and opens up the Puzzle World. The hat is part of a full wardrobe set which Henry must assemble to fix the damage he's done.
The Rosetta Rosso from Luminous Arc 2 all wear nifty hats decorated with roses.
Resident Evil's Jill Valentine wore a beret, until Tofu ended up with it somehow and when she joined the BSAA she started wearing a baseball cap.
Jack Krauser and Mikhail Victor also sport berets in their respective Resident Evil games. Honorable mention goes to the R.P.D. and their police caps. Too bad that most of them are zombified.
The main villain of Petz: Dogs 2 is a wolf with a magic technicolor top hat.
Pickory wears a giant purple cavalier hat which is bigger than he is.
In Hedgewars hedgehogs in each team are given their own hats, which currently is the only variable part of sprites. Lots of choice between various fruits, pumpkins, KISS hairdo and masks, Darth Vader's helm, cook's hat... you got the picture.
Fable II has several nice Enlightenment Era hats, ranging from tricorns to bicorns to top hats to wizard hats.
Carl Clover from BlazBlue wears a top hat several sizes too big for his age, and apparently hides a mechanical horse which acts as a weapon inside of it.
In the sequel Continuum Shift, Tsubaki Yayoi takes notes from Lelouch and wears a hat with wings on the sides and an eye on the brim.
Hazama is not complete without his signature Smooth Criminal fedora, either. Notably, he seems to be aware of this trope being in effect, (either that or he's just trolling, as usual,) as he doesn't catch himself when he is knocked down, but opts for catching the knocked off hat, instead.
Noel Vermillion and her blue beret.
Ojou in Suika absolutely refuses to remove her nice hat. It's black and has two bells hanging on it. It doesn't even come off when she's bathing or swimming. The closest to removal it gets is Hiroshi putting a 'second hat' (read: Archimedes) on top of her head.
Death's Hand has an impressive demon-face helmet that features prominently on the game's packaging.
Various girls in the Tokimeki Memorial series wears hats on some of her seasonal clothes, during Dating times. As a rule of thumb, standard pretty girls (ex. : Shiori, Mio, Miho) wear pimped-out or straw large hats ; Genki Girls (ex. Saki, Hikari) wear caps ; and Ojou and rich girls (ex : Yukari, Mei) wear berets.
Way too many characters to count in Mitsumete Knight, be it either male or female ones, wear hats with some of their thematic clothes. Even the Character Sheet's pics don't show them all.
In the Ace Attorney series, Jake Marshall and (in Apollo Justice) Phoenix Wright.
The Sly Cooper games have a couple of examples. Though the main character has a rather standard flat cap (which, admittedly, can be used as a land mine with a certain ability in the first game), Don octavio, a boss from the third game, wears a fairly nice opera hat (given that he is an opera-themed villain), but most notable is Sir Raleigh the Frog, the first boss of the first game, who wears what is possibly the greatest Top Hat in existence.◊
The iPod touch/iPhone games by Rocket Cat Games make it a point to include unlockable hats. Hook Champ includes the classic Indiana Jones hat, a rainbow wig, a football helmet, a giant fishhead, a tophat or two, a bowler, a moustache ("Facial hair is like a hat for your mouth), etc.
Many Italians in Assassins Creed II wear hats, while the lowest-ranking guards all wear berets.
In Jumper Three, there is a shop where you can buy loads and loads of useless-but-cool hats (and glasses).
Princess Alena from Dragon Quest IV wears a very distinctive Nice Hat. It's a sort of dark blue, brimless, crown-shaped hat with one cone-shaped protrusion from the middle.
Nice Hats abound in L.A. Noire, and there's even an Achievement for getting through a fistfight while retaining your hat.
Portal 2 has some rarer hats from Team Fortress 2 available in co-op.
In Dawn Of War: Dark Crusade, while assaulting the Imperial Guard stronghold with the Orks, Warboss Gorgutz will lament that the Commissar's hat gets blown away with his head, because he wanted it.
Kaptain Bluddflagg, the ork leader from Dawn Of War 2: Retribution, sports a truly inspired pirate hat. Furthermore, he is willing to search an entire sector for a renegade Space Marine commander and kill him, at the Inquisition's behest, for a fight with two imperial regiments and Inquisitor Andrastia'sNice Hat. The achievement for finishing the Ork campaign is even called Nice Hat, which is fitting since the ending involves Bluddflagg knocking Andrastia out and taking her hat, noting that the entire campaign "wasn't a total loss".
There's also King Graham's lucky hat in Kings Quest. Crown goes off, the hat comes on, and you know that the Quest's started.
Ninten and Ness the two main lead protagonists for Mother and Mother 2 wear red baseball caps as part of their trademark clothing. Though the tradition of the lead main protagonist in the Mother series wearing these was averted in Mother 3 with Lucas who still wears a striped shirt but doesn't wear any baseball cap at all. His father Flint on the other hand wears a Cowboy hat. All three games in the series even use Hats as a type of armor for the characters who wear one.
Cerebella wears a Living Weaponhat◊ named Vice-Versa. It consists of a pair of giant, muscular, gorilla-like arms with a skull-like face situated in the middle. She uses it as one would expect: to break people.
Peacock also sports a Nice Hat: She wears a large, tricked-out top hat that can among other uses turn into a bird's head and shoot a laser, serve as a Hammerspace portal, and also houses one of her cronies, a tiny peacock named Avery.
Gust and Blanc/White Heart from Neptunia have some pretty spiffing hats.
Official art for Tekken (it's on the back cover of the second game's manual) has Jun (yes that Jun) chilling on the beach with a straw hat.
Borderlands: 2 different DLC packages include Mad Moxxi who wears one. The Zombie Island of Dr. Ned DLC features Hank Reiss: Wereskag. His hat was made by his young daughter and looks like it was decorated with macaroni.
LEGO Star Wars: some levels require the use of hat dispensing machines in order to wear a disguise. Other dispensers only dish out cool hats.
Bill in Left 4 Dead wears a green beret, the same one he used during his service in the military and wears it while kicking zombie ass in the present time. Bill's hat can also be obtained in Team Fortress 2 and the characters there agree that it is a nice hat.
Many of the citizens in GTA vice City wear Nice Hats that never come off no matter how many time you beat, stab, slash, shoot, blast and burn them.
League of Legends: Jarvan's crown, Caitlyn's flared top hat, a surprising number of helmets, Lulu's and Veigar's pointy numbers and Twisted Fate's cowboy hat would all qualify. Once variant skins are factored in, the list rapidly gets silly.