I've gone back and forth from long to short a number of times, so I know what you mean about liking to change styles.
Its hard to say what work best for you without knowing what type of hair you have. My hair is curly, so I pretty much have to do it everyday, or just pull it back, I can't pull off the roll out of bed look. If you have straight hair though, you could just get a chin length bob where you could still have fun with it, but also just let it dry naturally. I hope you find something that works for you!