Ok, I found a few pictures of me that show my haircut at a couple different stages, see which one you like best. ^_^
Kind of messy hair-Medium length
*This is a picture of me from a couple of months ago. I was at a friend's house for dinner. My hair was at a medium length chop, and looking kind of messy and good. Note the layers on the sides and bangs style.
A bit longer on the sides
*This was taken on Christmas. My hair was at the longest I let it grow to in this style, but it still looks good to me. This style is good because even when it gets to be a bit longer, it still works. I'm with my boyfriend at my Grandparents' house in the pic.
Right after I had it cut
*This was around Halloween, like a week or two after I had it cut. This is when it looks more stylized with the layers and such.
I think you'll love the hairstyle if you decide to go with something similar to it. It's super easy to take care of, just blow dry it straight with your hands, put a little bit of spray on if you like(not necessary for daily wear), and you're ready to go. It also looks good for a couple of days after you dry it, so you only need to wash and restyle your hair every couple of days. Keeps the hair healthy.
Good luck!