It could be 'Anne of the Green Gables'.
If the girl was orphaned and the story is historical then it should be Anne. I was just looking for the same things.
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Mark is described as a nerdy teenager with glasses and that his hair is always overgrown. Courtney is described as being very pretty with long brown hair, freckles, and gray eyes.
Girls with long brown (curly) hair, and tall, about 5'10.
The name of the main character is Duck. She has long, braided, red hair. She is actually a duck, who was turned into a girl, who then turns into Princess Tutu. As I said, her name is Duck and in the Japanese version her name is Ahiru, which is the japanese word for duck.
Yes, Harry likes long and short hair on any girl
Angelique Cinelu - look her up on MySpace