What sort of hair colour were you thinking? You could probably achieve a nice, intense red if you lightened what you have now and put a red dye on top. This colour is pretty awesome
As for hair cuts, Betty Page style bangs/fringes are kinda popular with the style you are wanting to achieve.
I guess I'd would suggest leaving it as long as possible and asking for soft layers so you can create curls and rolls.
On days when you don't want to syle it, put it up and tie a bandana around it!
Not sure if that helps, but there is a tonne of inspiration on the net if you Google it