Answer:
Shorter than my four siblings, but easily the strongest, Sometimes I wear a funny hat.
What is flat, usually square, and made from trees but isn't wood?
Boxers do this for a living and kids do it in the backseat for free
What has a foot but no legs?
I can be moved. I can be rolled. But nothing will I hold. I'm red and I'm blue, and I can be other colors too. Having no head, though similar in shape. I have no eyes yet move all over the place.
Dark, feathery, and popular in Baltimore and fantasy books.