Rarely will anyone ask why it doesn't just fly off without its wearer...
- T he Take-copter from Doraemon, which is so iconic that it's one of the few recurring tools even if technically its functionality is covered by other gadgets.
- In To Love-Ru, Lala's hat has giant bat wings and allows her to fly. Her entire costume (hat included) is a shapechanging robot named Peke, so the antigravity may come from the entire costume, rather than just the hat. Her Magnet-bot technology, which sticks things or people together would also allow the hat to stay on.
- The Argentinian comic (and a cartoon) Hijitus has the eponymous hero use a magical hat (about as big as himself) to transform into a Flying Brick.
- In Calvin and Hobbes, Calvin orders a propeller beanie expecting that it will allow 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.
Calvin: Well, how does it look?
Hobbes: Adjectives fail me.
Calvin: I'm turning it on. Ready? Here goes. I don't seem to be lifting off. This is very peculiar.
Hobbes: That's the word I was looking for.
- The eponymous beanie in the children's book Isabella Propeller and the Magic Beanie.
- Sister Bertrille, of The Flying Nun, is able to fly because of her winged cornette catching the wind and lifting her up.
- 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.
- A Mystery Science Theater 3000 episode has Joel coming up with the "Beanie-Chopper" during the invention exchange, but to the Bots' disappointment it doesn't actually allow him to fly.
- 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. It also answers the question posed in the description, the Propeller Mushroom that gives you the power does fly away if you don't reach it quickly enough...
- Wario Land had a jet-powered hat as one of the power-ups.
- The 1992 The Addams Family videogame (based on the 1991 movie of the same name) gives Gomez a helicopter hat in certain levels.
- Barbara and her sisters in Rayman Legends use their winged helmets to hover, due to lacking the titular hero's Helicopter Hair.
- Propeller Knight from Shovel Knight has a very fancy helmet with a propeller that lets him fly, complete with handles.
- Risky's Hat in Shantae and the Pirate's Curse gives Shantae the ability to glide due to its large size and consequently fly whenever there's an updraft.
- In Splatoon 2, Chinooks wear apparatus on their heads with propellers to air-drop their fellow Salmonids from the Mothership to the ground.
- The playable Furby in Big Fun in Furbyland's Mini-Game In the Clouds wears a propeller hat that grants it flight.
- 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. And as a backup, if the chinstrap gets cut, he can hold onto the (very subtle) brim.
- In League of Super Redundant Heroes, the Evil Savant's propeller beanie can fly, although he's only used it once so far.
- The Order of the Stick: A gnome in Tinkertown is seen flying with a propeller beanie.
- Inspector Gadget has a helicopter hat. Why it doesn't fly away is actually shown, in that it usually has handles that he holds onto while flying, both to steer and prevent it from coming off.
- In one episode, it did. He had to call out, "Go-Go-Gadget Copter Spare!" to get another one.
- Verne is shown with one in the Back to the Future Animated Adaptation.
- In an intro sequence from Huckleberry Hound, Pixie and Dixie give Mr. Jinks a "copter cap", which sends the cat flying.
- The Mask once wore a propeller-beanie which actually worked as a real helicopter when he pulled on the propellers.
- The "propeller beanie" (a beanie or baseball hat with a propeller on it) has become a nerd symbol. For example, Google gives its new employees ("Nooglers") a propeller hat in Google colors during orientation.