Serious question:
My hair is now at a length where I am considering a head/hairband, I'm leaning towards thicker one but open to suggestions
Both of them can slip through your hair and it's going to annoy you. I had a haircut almost 2 months ago, before that I just grew it up for 2 years. I recommend you to buy something like this:
It's a real life-saver for the people with long hair.