Thanks GecT,
I used a lattice and sculpted it onto a circle- I still have to learn about the bend deformers. In fact I don't know anything about the deformers yet.
I'm getting there with the model though. The head band looks pretty bad at the moment, but the general shape is there:



and the first render- no lighting or materials (besides a basic cream colored phong).



I'm already wondering about how I can texture the leather parts? Can I get the creases to show using a bump map?