1. Their horns get in the way.
2. The wind steals them whenever the dragon flies.
3. Knights laugh when they see a dragon in a ballcap.
4. Hats catch fire too easily around the hatchlings.
5. They don't fit properly, since no one bothers making hats large enough for a dragon's head.
6. Because princesses get frightfully aggressive if you try taking their headwear, and no dragon wants to explain how they lost an eye to a princess' pointy hat.
7. Villagers never notice them. What's the point of wearing your new hat to a raid, if no one pauses in their screams long enough to compliment how well it matches your scales?
8. Because heroes always assume it's a magical hat, and steal it before you get a chance to wear it.
9. They itch, and no dragon likes having an itchy head.
10. The hat smelled tasty, and dragons get hungry.
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