If you do it wrong, you look like trying to hard. If you do it right, it's adorable.
I agree, using a wax or some kind of texturing is necessary. usa a good round brush when blow drying to get that much volume. I had my hair like that and IMO, when you want your hair cut like that, it's got to be all one even color. I had uneven highlights and 3 different colors in it and it looked like a mess.