I'm afraid of growing old and unattractive. But what bothers me even more is that I am actually shallow enough to think this way. I guess I value good looks and external beauty way too much. I imagine that if I had a proper attitude on life I'd be perfectly content and happy to live as a wrinkly old woman whom no one looks at. But how do I get there?
I think that the way to be content with the inside rather than the external is to focus on the internal and develop an appreciation for it. The more that we focus on the external and the physical shell of the body, the less we are focused on the inner soul and the spiritual dimension. Perhaps you can begin learning more Chassidut--a deep teaching that stresses the spiritual dimension over the physical. You will find many wonderful articles on our site (check out our Spirituality section). The more you appreciate and develop your taste for the beauty of spiritual concepts and ideas, the less significant the physical will become to you.
Try to train yourself to look at the quality of a person, his characteristics and refinement, rather than what you like about his or her external appearance. Ask yourself what qualities you like about people and look for and focus on those qualities. Try to develop in yourself the qualities that you admire, and ask yourself daily what you have done that was kind, generous, caring, etc.
Perhaps another idea is to spend some time with older people. You could visit them in a home for the elderly, or choose a neighborhood senior to pay home visits to. As you spend time with the elderly, you will begin to see how much they have to offer, and how much wisdom and wit they possess, despite having a frail or wrinkled body. This should change your perspective on the elderly and on people in general in a significant way.
You have, in fact, already made the most important first step: you desire to change your perspective. You have already decided that you want to mature beyond a narrow vision of self as a strictly physical being. If you remain committed to your internal growth, you're sure to succeed.