1. He has no idea how cool he is. Or "when" he is.
2. His name is Ichabod Crane. Legit.
3. He's still rockin' that 18th century swag.
4. He speaks Olde English.
5. He was into witches before they were hot (from burning at the stake).
6. He is not a fan of modern technology.
7. He makes that long hair and scruff look hot!
8. He's got a great body without ever having been to the gym.
9. He doesn't like labels.
10. Nobody understands him.
Like all hipsters, the only people who understand Ichabod Crane are dead, trapped in limbo or evil.