This site has definitely got potential. You should let users upload their own pictures and implement some kind of hot or not style rating feature. You've definitely found a good niché to target. It's just so nice to see a website listed here that isn't another design portfolio or proxy website.

How 'good' would you say you are with hair styling? I:E If someone gave you a pic of their hair as is, and a picture of what hair they want, would you be able to tell them either A) How to get it cut, or waht to tell the barber to do, or B) Tell them exactly how to style it?

Just take the picture into the barbers.