Hair Dilemma

I'm debating whether to cut my hair. I like it long enough to pull back, but I also like it short enough where I don't have to. Almost everything I've read suggests shorter hair is easier to deal with in boot camp, and I've never been one to put in a lot of effort into my hair. With summer coming, short hair won't be bad at all. Currently, my hair is around shoulder-length. If I cut it now, there's no way it will be long enough to pull back by October, so it will have to stay short. This is the style I'm thinking about (I know, I know. I'm a dork, but it's really cute).