Oh, dear Lookernomore, don't give it too much of your precious time and attention! Aging is difficult but we need to learn how to accept the new versions of ourselves. You say you were pretty when younger but I bet you still are! You just concentrate on the changes that aging brings and forget about all the good things.
The haircut is a difficult thing to find, I agree. Try different online resources to see if some particular haircut will suit you and contact the hairdresser when possible. The same things goes for the makeup, if you think it will help you to be more confident. There are online programs that add makeu for your pics for you to see whether it will suit you, like Photodiva does.
Or do none of this things! Try to get more sleep, drink more fresh water, take walks and keep fit, if possible. If you take care of yourself, you will feel better, I promise!