Well my first hat might not have been pretty but I did it. When looking at a completed crochet hat it looks so much more complicated than it is. I believe starting the ring and keeping track of what row you are on is the hardest part.
I picked a really simple pattern for my first hat, Double Crochet Hat Pattern, you can find the pattern here. I don't think it gets any simpler than this. I used Red Heart Ltd Eco-Cotton blend. 75% recycled cotton and 25% acrylic. My mom loved it so much when I was done with it I gifted it to her. The cool thing is she didn't just put on her shelf, she actually uses it.