How do I go about growing my hair out?

I just got a haircut a couple of days ago and I'm finally noticing that I look better with more hair because of my face shape. My hair is now like Tom Cruise's in the first Mission: Impossible. It's just long enough though that I can have that messy look. However, I've had this style before and I want to try that Ashton Kutcher or Tom Cruise-M:I 2 look. I have fine hair though, so my hair might be flat on top if I grew it out.

So, with this short haircut now, what do I tell the stylist when I get my haircut every 6 weeks or so? What do I do about the back, the bangs, and the sideburns area. Do I wait longer in between haircuts and/or gradually increase the blade size?

Thanks for your help.

get a trim like every other month for it to be healthy