How do I hide my hair without it looking stupid?

I have very curly hair, but I can clip it up very well under a hat, but I am not cutting it until I get it straightened perminately, and I don't want to wear a wig XD I'm thinking of crossing dressing, is why I ask. And on the same topic! Have any tips on chest binding? Everytime I try I find it very restrictive, I'm going to try neoprene waist control things tho XD sooo?? Thanks! ;)