I just wrote this to a woman on a different forum, who wanted to know what to do about her insecurity about her looks. I figured I'd cross post it here to save. Let me know what you think.~~~
From the ages of 14 to 18 I was a junior's size runway model. (I obviously didn't grow up frum! LOL) My agent was awesome. She knocked sense into our heads early on. She used to be a star model for Oscar de la Renta. She told us "No matter how pretty you are, or how thin you are, someone will always be prettier or thinner. Get used to it. Remember, in this business you are nothing but a glorified clothes hanger, and you can all be easily replaced! Don't go getting stuck up, you're just as human as anyone else."
I realized that if G-d forbid something were to happen to my looks, like an auto accident or something, that I'd better have some value inside of me in order to keep my friends. Looks can be taken away from you in a split second, but no one can take away your middos, your loving nature, and your love of Hashem.
My daughter sometimes compares herself to other girls, and she asks me who I think is prettier. I tell her that this friend looks exactly the way Hashem wants her to look, and that DD looks exactly the way He wants her to look. We are all who we are, because that is who we are supposed to be!
As far at "attractiveness" goes, I know some really knockout beautiful women, who have no so nice middos or a sour attitude about life. After that two second first impression, you get to realize that they're not so pretty after all. I also know some very plain, overweight, frumpily dressed women who LOVE LIFE, and always run to help others. They're genuinely happy to see you, have a big smile and a warm hug. Those are the women who are truly beautiful.
There is nothing more attractive than a woman - in any sort of "packaging" - who is truly happy. Being beautiful won't make you happy, but I promise you that being happy will make you beautiful. Like everyone else said, work on your attitude, middos and emunah, and next thing you know, you'll be walking down the street glowing, with your head held high and a smile on your face. When you look in the mirror, you'll love who you see - because Hashem made you, and has loved you all along.