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Anime and Manga

• 

  Dr. Black Jack in Black Jack.

• 

  Iono Mito Archeline Iono the Fanatics.

• 

  Hecate from Shakugan no Shana.

• 

  Vita's hat, personally made for her by Hayate-chan, from Magical Girl Lyrical Nanoha.

• 

  Alucard from Hellsing.

• 

  Lala and her Nice Hat, from To LOVE-Ru

• Cosmo Queen in Yu-Gi-Oh Card Game.
• Lelouch Lamperouge's in Code Geass
  • The even-more-ridiculous concept art.
• Natsumi of Mahou Sensei Negima: 1, 2.
• Firo Prochainezo has the best hat in the world.
• Here's Zelgadis from Slayers with one.
• Takeru 's hat once and before ^{[dead link]}
• Tommy Himi's oversized orange newsboy cap
• One hat isn't enough, so Jonathan Joestar got three.
• Nadeko from Bakemonogatari: 1, 2
• Jigen Daisuke from Lupin III: 1, 2

Art

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  The statue of David by Donatello.

Comic Books

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  The Bat Hat from Superman: Red Son.

• Jay Garrick, The Flash's hat.
• Superman King of Earth's hat.

Literature

• 

  The Lord of the Rings: Gandalf has a Nice Pointy Hat

Live-Action TV

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  Jamie Hyneman of MythBusters is rarely seen without his trademark beret.

• Doctor Who: Since most Time Lords dress like this it's no surprise the Doctor's had a few.
  • Four's floppy hat: 1, 2
  • Five.
  • Seven.
  • Eleven's Crazy Awesome crime against fashion fez. And again.
  • And his Stetson
  • As of the new series trailer, the Stetson is back!!!
  • River's Nazi hat.
• Firefly: Jayne Cobb's cunning hat -- his mother made it for him.
• Joe Galliano, brother of John Galliano, on Conan.

Video Games

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  Suwako Moriya from Touhou.

• 

  Team Fortress 2, "America's #1 war-themed hat simulator", has a Nice Hat Magazine in-universe

• Team Fortress 2, "America's #1 war-themed hat simulator", has loads of nice hats.
• A Red Mage from the Final Fantasy series.
• Raidou Kuzunoha XIV from the Shin Megami Tensei: Devil Summoner series.
• Mouri Motonari ^{[dead link]} from Sengoku Basara, with many variations ^{[dead link]}.
• Every protagonist from the Pokémon series.
• From Mortal Kombat:
  • Kung Lao
  • Raiden

Web Comics

• 

  Gil's fabulous hat from Girl Genius.

• 

  Ta-dah! (Gil's fabulous hat is so fabulous, it gets two images here!)

• Courtyard Droll's hat of amazing proportions ^{[dead link]} from Homestuck.

Real Life

• 

  Aretha Franklin wearing her fierce hat at President Barack Obama's inauguration.

• A golden hat from the Central European Bronze Age.

  A golden hat from the Central European Bronze Age.

• Otto von Bismarck, wearing a Prussian cuirassier officer's helmet.

  Otto von Bismarck, wearing a Prussian cuirassier officer's helmet.

• 

  U.S. President Calvin Coolidge, tipping his hat. The hat was the special headpiece of the Smoki Indians of Prescott, Arizona. It had a rim of brilliant red and a crown of bright blue. The Smoki Indians were a fictitious tribe created in imitation of the local Hopi Indians that performed at Prescott's annual rodeo. The president was inducted into the Smoki tribe on the grounds of the White House on October 22, 1924. On June 2, 1924, President Coolidge had signed a bill granting Indians full U.S. citizenship. (Wikimedia Commons)

• Princess Beatrice, 'nuff ^{[dead link]} said ^{[dead link]}
  • Matt Smith in Beatrice's hat.
  • More royal wedding hats anyone?
• Eijiro Miyama: Bet your hat doesn't have live goldfish in it.
• Namgar honors her Buryat heritage with this hat with a Siberian Ibex on it ^{[dead link]}. Seriously, Buryats and Mongols have an awesome pointy hat to call their own ^{[dead link]}.

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