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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

• 

  The statue of David by Donatello.

Comic Books

• 

  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

• 

  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

• 

  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.

• 

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

• 

  Calvin Coolidge and his Nice Hat

• 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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