One of the key factors to crossdressing effectively and convincingly is the subject of makeup, and indeed, I don't think there's a crossdresser alive which can get along without some form of makeup.
However, makeup can be your ally and it can be the cause of your downfall. The reason is that many wannabe cross dressers don't really know how to apply makeup and end up looking much worse than they hoped to be. Let's see what's the biggest mistake of crossdressing makeup is and how to avoid it.
The biggest make up mistake cross dressers make is to apply to much of it. It's easy to get carried away, so I don't blame you all that much, but know that putting on to much make up is like placing a sign on your forehead screaming “look at me. I've got something to hide”.
Remember, Makeup is meant to conceal what you don't want other people to see and to highlight what you do want them to see. But putting on too much make up just highlights everything, including the your masculine features.
Think of it this way, have you ever seen a truly beautiful woman wearing too much makeup? The answer is no. They use makeup to highlight their natural beauty.
In fact, one of the stereotypes about crossdressers is that they wear too much makeup. The way to avoid it, other than learning how to apply makeup, is to do it in stages, asking yourself on every step: does this help me look more feminine in an unobtrusive, under the radar, way, or does it seem too much? You may make mistakes in the beginning, but soon you'll have a real knack for when enough is enough.