To Cut or Not to Cut?

So my wonderful flat iron finally died so I been wearing my hair basically in a pony tail the past week. I really am having issues too with the gray hairs.
Anyway I am dying to do something with my hair and debating on cutting it again..I really would like for it to grow out. I am withholding to do anything though until I go on my New York trip....so the question is to cut or not to cut.
If I do decide to cut it I am probably going to do this..

However I am thinking about growing it out and just doing it classic pin up Betty Page style like this....

I guess I will know what to do when the time comes.