i always do this! i have a lot of t-shirts i made myself! Quotes and Pics! But my tip is: if you use a thicker kind of paper, like couche paper, the paint won´t spread and you can make another coat of paint and it won´t rip!
button headband, cute! Measure a piece of elastic around your head, sew it into a headband and then sew on buttons! Lots of buttons! You could even use a headband from the store. Its perfect with a messy ponytail.