Here is the way I do my crossplay makeup! It came from a lot of trial and error, and from reading tutorials and adapting the techniques. In the same way, this tutorial can give the general guidelines (or at least I hope it can), but know that everyone is different and may require a different makeup to achieve the desired look and that it’s up to you to experiment. I would say the best way to know where you need to put shadows is to look at yourself in the mirror while under an overhead spotlight; the natural shadows you see are the ones you need to recreate. Also keep in mind your character, his age, traits and complexion, and the colors you are wearing; not two of my crossplays have the same makeup.
Always take pictures of yourself when experimenting, otherwise you’ll only see yourself in the mirror and think you look awful (I still do everytime). Pictures give you the objectivity to judge your work instead and see how you can improve. Drawing over pictures of yourself in Photoshop can be good practice too!
Don’t forget to apply your makeup in a light similar to that of the convention center or photo shoot emplacement where you are going, as to correctly gauge the shadow intensity needed.
I don’t talk about highlights in this tutorial because my skin is already too pale as it is, but if you have darker skin or are wearing a darker or unnatural color in body paint, the places you can lighten are the brow, the nose line and the chin. With the body paint, I recommend using very dark of the same color on the eyes and medium dark for the other shadows.
This is personal but I am a firm believer against the use of eyeliner and mascara in crossplay (except if you’re doing stage with it, then by all means go ahead). Unless your character would wear makeup himself, I feel you shouldn’t look like you’re wearing any, otherwise you’re harming your credibility. This is why I prefer to keep to natural colors and undefined applying.
This tutorial may not be enough for those with very feminine features. In this case, prosthetics may be needed for a successful look.
I’d be happy to answer any questions or to go into more detail or theory. And I’d love to hear from anyone who tries it out!
(Please note that I am in no way an expert in makeup; disagreeing with any of my statements is perfectly valid. )
EDIT: I've been asked about the eyebrows a lot: I don't literally lower my eyebrows by covering my own and painting new ones, I merely add more under my own and towards the nose. The covering technique can work as well, of course, there are a lot of ways to go about it. ...Sorry if that was confusing.