Is there any such thing as a headband that doesn't hurt your head? Today I started out with this big bow one that made me feel like Minnie Mouse, but by 10 am it was giving me a headache and I had to take it off. It seems like even soft, cloth-y ones that feel great for an hour eventually turn on you. Do I just have a sensitive head?
(PS, look at Jane behind me all unaware that she's in my photo.)
I love everything about this headband and your look with perfectly trimmed bangs and polka-dot dress so I understand your frustration at not being able to stick to the look for more than a few hours. Unfortunately, I don't think there's such a thing as non-painful headbands. They do stretch as you wear them so maybe you can find something some kind of round surface like a jumbo coffee can to stretch it out on. Be careful that you don't stretch it out so much that it won't stay on your head because that is a bummer. And yes, that totally happened to me.
If after trying everything it's still pain city maybe you can take the bow of the band and glue/sew it on a thick ribbon that you can tie around your head? Still cute and won't hurt!