Animate Inanimate Objects, the Living Hat is most likely unable to move about on its own and has to rely on his wearer... but that doesn't mean it can't spell trouble. After all, as a magical object that goes on a person's head, the Living Hat is very likely to be some sort of Mind Reader.
Naturally, a subtrope of Living Clothes, itself one of Animate Inanimate Object. Also see Head Pet, for pets who just happen to prefer to nestle where a hat would go, but don't particularly resemble hats. Unrelated to Planet of Hats.
- In The Parselmouth of Gryffindor, based on the Sorting Hat's existence, Hermione Granger mistakenly believes that Professor Quirrell's Turban is both alive and evil. Even after they realize the turban just serves as a way to conceal what is really possessing Professor Quirrell, they keep calling Voldemort "the Turban", to everyone's confusion.
- The Touhou fandom gives this treatment to Suwako Moriya's hat (named Pyonta), to meme-like levels. In some works it's an extension of her body, in others it's a pet, and in others it's an outright malevolent lifeform controlling Suwako via tentacles in her brain.
- In Diamond and Silver's Excellent Adventure, Baron Zeppeli's top hat has legs and claws, and is actually responsible for brainwashing him into being evil. (It's also a Shout-Out to Doris from Meet the Robinsons; the characters in this fic lampshade the similarities.)
- In Disney's Make Mine Music, the segment Johnny Fedora and Alice Blue Bonnet is a love story about two hats who are separated when Alice is purchased.
- In The Legend of Frosty the Snowman, Frosty's magic hat is depicted as this.
- In Meet the Robinsons, the Bowler Hat Guy's bowler hat, Doris, is sapient and mobile, actually serving as the Hypercompetent Sidekick to her wearer while she waits for a chance to take over the world.
- The Archchancellor's Hat in Sourcery is the malevolent token of authority of the Archchancellor of the Unseen Academy for Wizards. It progressively gained sentience after being worn by over two hundred powerful wizards over hundreds of years, and seeks power at all costs, manipulating new wearers to its own ends.
- The Sorting Hat from Harry Potter. Every year, at the Sorting Ceremony, all the students try on the Hat, who reads their mind to see what House would suit them best based on their personality. The Sorting Hat is one of Hogwarts' most prized possessions, and, fortunately, a "good" character.
- In Warhammer Fantasy, the Crown of Sorcery was an ancient artifact made by Nagash, the first necromancer. It's vaguely sentient and tries to dominate its wearer so it can be reunited with its creator. Its most famous appearance was when it halfway succeeded in possessing the orc warlord Azhag the Slaughterer, whispering plans and tactics into Azhag's mind that brought him great success, but orcs are highly resistant to psychic powers and thus spent of lot of time appearing to argue with himself.
- Super Mario Bros.:
- Fallen London:
- The Extraordinary and Judgemental Hats can speak.
- The Blemmigan Hat is a walking mushroom creature that rides on your head and tries not to wriggle when anyone is looking.
- Polythreme is a Genius Loci where everything is animate; if you go there, all of your clothes will try to rebel against you.
- Fantastic Night Dreams Cotton has Needle. Not only serving as Appli's hat, but also a caretaker. He's even a Family Man!
- In Guilty Gear series, there's I-no, a servant of That Man that fights with an electric guitar, and she also wears a pointed witch's hat that can fire projectiles, which also looks like a skull.
- Planescape: Torment: Optix is a gear spirit from Mechanus that takes the form of an eyepiece useable by modrons. When equipped on Nordom, he provides a number of bonuses but because he doesn't like to leave when he gets comfortable it takes a Remove Curse spell to remove him (though unlike a true cursed item, wearing him doesn't penalize Nordom in any way).
- In Skullgirls, Cerebella's Vice Versa is a living hat with arms that assists her in attacks.
- In Yo-Kai Watch, Wazzat is a Yo-kai who is a living hat. He was once an ordinary hat, but after being neglected the negative energy of his abandonment ended up giving him a mind of his own. He tries to perch on other people's heads which had the side effect of erasing memories.
- In The Legend of Zelda: The Minish Cap, Ezlo (the titular hat) is one of these. He also serves as Link's hat over the course of the game, able to shrink him down to the size of a Picori whenever needed, and as the game's Exposition Fairy. Midway through the game, he reveals that he's actually a Picori mage, but was transformed into the hat by his apprentice Vaati.
- Kirby's Return to Dream Land's Master Crown is at least implied to be sentient, with it visibly wobbling on Magolor's head. It also grows when its user decides to take on its power, and later Magolor Soul is mentioned to be "a sad shell, nothing more than a manifestation of the Master Crown itself".
- In Hazbin Hotel, Sir Pentious's top hat serves as an Expressive Accessory, with an emotive eye and mouth that consistently change to match Pentious's expression, prompting Angel Dust to ask if the hat is alive. Pentious, after stopping himself from reflexively explaining, replies that that's none of Angel's business, leaving the hat's status ambiguous for the time being.
- In Charby the Vampirate, Kavonn's hat is a sentient entity that is the source of his power and can communicate with him. She prevented him from growing any taller than he was when he first acquired her and provides him his outfits while trying in vain to also control his haircut.
- Wander's hat in Wander over Yonder is implied to be sentient. Mostly it acts as a Bag of Holding that gives the owner what they need for a particular situation. This is highlighted in the episode "The Hat", where Wander goes missing and Sylvia has to use the hat to find him, but everything the hat gives her results in her almost being eaten by a giant worm which is what the hat wants, since Wander had been swallowed by the worm. When Sylvia argues with the hat, it appears to smile or frown as a response.
- In the Mickey Mouse short "Mickey's Grand Opera", Pluto finds a magician's hat that moves on its own.
- Goof Troop: The episode "Talent to the Max" features a talking magician's hat that makes Max a talented (and narcissistic) magician.
- Darkwing Duck has a species of Puppeteer Parasite aliens who looked like hats.