@clintflint - I think there are some websites that can help out with the face shape thing. They let you put your photo in and then put different styles over it.
The thing I look for, above everything else, is how much time it takes to prepare a hairstyle. I wouldn't get this one, for example, because I have fairly wavy hair and it seems to be the kind of thing that you really need your hair to be dead straight every time to pull off.
It might look good if I spent an hour with the straighteners every day, but I'm not willing to do that. I have enough to do every day without adding in an hour of messing around with my hair.
I like a look that will look good whether I have ten minutes to spare on it, or an hour. But, if you had dead straight hair, I think this look would be fairly easy to maintain.