I don’t wear makeup. At all. Never learned how, and never had any interest in it.
But…I’m doing a crossplay (cross-gender) costume for Comic Con, and I’d like to use makeup and shading to help achieve the look I’m going for (I’m female, and my costume is male–the Tenth Doctor). I’ve found some advice on the net, but all of it seems to assume some knowledge of makeup technique to start with.
Ideally, I’d like to find someone I could pay to give me a lesson or two and show me which products I need to buy (so someone in person rather than online). I don’t think I can just go to a makeup counter at a department store–can I? Wouldn’t they be much more focused on a more traditional female makeup style?
The spouse suggested a theatrical supply place (which we do have near here) but I thought maybe not because stage makeup isn’t what I’m looking for either. I essentially want natural looking makeup with some subtle shading to “masculinize” my face for the costume. Maybe I need to see if I can find a friendly drag king…
Any ideas where I might look, or advice?
You may as well try the theatrical makeup place. A makeup artist needs to know how to paint believable faces for 1000 and 100 seat theaters alike.
In general, highlights will make things look raised up and shadows will make things look sunken in. So get a nice picture of your face and a nice picture of David Tennant and look to see where you both bulge and sink and then try to recreate the hills and valleys of his face on yours. A smooth transition from highlight to shadow implies a gentle curve, while a sharp split implies an edge
Masculine faces are sharper and harder-edged than women so you’ll need to run a line of shadowing underneath your chin and cheeks like a chin strap beard but on the underside of the face and match it with highlight along the top. That will give you a stronger jawline. Men’s skin has more texture to it so once you’ve got a layer of foundation, lightly stipple some yellows, reds, and browns to your face to give it a feeling of larger pores and slightly rugged. I’d also stipple black along the lower cheek and chin because he tends to do a bit of a 5 o’clock shadow.
It’s rather expensive but Stage Makeup is a phenomenal resource in these matters.
Thanks, great advice!
It’ll be a little easier, I think, because I’m not actually trying to look like David Tennant. That wouldn’t be possible, given that I’m toting around quite a few more Adipose babies than he is. 
I’m just going to try to get the hair right, and I’ll be happy if I can fool people from a middle distance into thinking I’m a guy and they can tell who I’m supposed to be by the clothes.
That book looks cool indeed, but yeah, that’s pretty pricey for a one-shot gig.
Is there a high school or community college with a theater group in your town? Perhaps you could hire one of the theater students to do / teach you character makeup.