Fashion knows no bounds. As long as it can be in trend, it can be a thing. All that you have to do is follow along in the footsteps of the idol you want to be like, and you shall be guided along just fine. But then, everybody knows that such things cannot be done for everything. Some things work for people differently. There are certain trends that are in a fashion which cannot be indulged into without having proper guidance. Ear stretching is one of those things. You have to be sure about the fact that you are interested enough in this not to back away at the last moment.
Do not try to get it done all by yourself, stretching is a time taking process and you have to make sure that you are devoting significant time to the process and not skipping through the rings. If you do so then you stand the risk of suffering permanent injury to your ear. Unless you want to end up getting disfigured permanently, take it one ring at a time. There are saloons available that do the process systematically and with the due medical attention.
You start out at the lower range of rings. If you have no prior experience with piercing then you start with a simple piercing. From then on you start to use appliances and tools that keep your ears stretched. After you develop comfort at one stage you move on to the other and then further. How further you want to go is entirely up to you. Many people choose to stop after reaching a certain limit on their rings. Others, they want to go till the very far out.
Take into consideration before starting out. What you require matters the most.