Hat of Flight

A Cool Hat or Cool Helmet that gives the wearer the ability to fly. Often has wings or helicopter blades.

Rarely will anyone ask why it doesn't just fly off without its wearer...

Compare Helicopter Hair and Hair Wings. See also Mercury's Wings. Subtrope of Hat of Power.

Anime and Manga

 * Doraemon: the Take-copter, which is so iconic that it's one of the few recurring tools even if technically its functionality is covered by other gadgets.

Comic Books

 * The Argentinian comic (and a cartoon) Hijitus has the titular hero use a magical hat (about as big as himself) to transform into a Flying Brick.

Literature

 * The eponymous beanie in the children's book Isabella Propeller and the Magic Beanie.

Live Action TV

 * The Flying Nun
 * Linda finds a magical hat that allows her to fly in the Round the Twist episode "Copycat".
 * In the Sid and Marty Krofft show, Lidsville, the evil magician Hoodoo has a top hat that turns into a flying machine.

Newspaper Comics

 * In Calvin and Hobbes, Calvin orders a hat with a propeller on in, expecting that it will alow him to fly. There is an Imagine Spot of him flying with it. He is quite disappointed when he gets and and find out it doesn't actually enable flight.

Oral Tradition

 * The Trope Maker is probably Hermes' winged hat, called the Petasus, though it was only 'winged' in that it had a wide floppy brim, and his power of flight came from his sandals. Nevertheless, because of Popcultural Osmosis, he is now often portrayed with a flying hat.

Video Games

 * The Wing Cap from Super Mario 64.
 * New Super Mario Bros. Wii: the Propeller Suit has a helmet with a propeller to use in flight.
 * Wario Land had a jet-powered hat as one of the power-ups.
 * The 1992 Addams Family videogame (based on the 1991 movie of the same name) gives Gomez a helicopter hat in certain levels.

Webcomics

 * In Basic Instructions, Rocket Hat's "superpower" is owning a rocket-propelled hat. The question of how it stays on his head is asked and answered -- chinstrap.

Western Animation

 * Inspector Gadget: the eponymous hero has a helicopter hat.
 * Verne is shown with one in the Back to The Future Animated Adaptation.