I like to cosplay at conventions, and usually I crossplay (dressing as male characters). I’ve watched a few tutorials on how to use makeup to masculinize my face and I’d like to try it.
Problem is, I’ve never worn makeup in my life, and when I walk into a makeup store (or even peruse the makeup aisles at Target), I feel like a squirrel trying to comprehend quantum physics. There are so many brands, so many types, so many of everything that inevitably I stand there for a while staring at all of it in confusion and then leave, figuring this has to be a bad idea. I’m definitely too nervous to ask one of the perfectly-made-up women who always work at stores like that for help. I’m sure they’d be nice, but I’d be so intimidated I’d probably miss most of what she said.
Naturally, I thought of the Dope. Can some of you makeup-knowledgeable folks out there help me out by answering a few questions?
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How do I figure out which one to buy? Are they all basically the same, or is there some subtle difference I’m missing between brands? At places like Ulta, there are like a million versions of what looks like the same thing under different brands. I assume more expensive ones are better, but define “better.” Where’s the line between “this is crap, don’t buy it!” and “this is relatively inexpensive but will do you just fine” and “this is way too fancy for what you’re trying to do”?
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How do I figure out which colors to get? They don’t have testers anymore (not that I’d use them anyway, because eww) so how do I know? The concealers and foundations, especially, have a bunch of colors that look very similar.
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From the videos I’ve been watching, it sounds like I need some kind of eyebrow pencil/brush to thicken my eyebrows, some kind of foundation (but not all over my face, which would look too feminine), concealer for the dark circles under my eyes, and taupe-colored blush to emphasize my cheekbones and jawline and give me more deep-set eyes. Does that sound about right? Do I need anything else?
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How do I know I’m not using too much? I feel like I’d have a tendency to do that so I could see the results better, but this isn’t for the stage. It’s supposed to look natural in a real-world situation. Is it just a trial-and-error thing? We’ve all seen those folks who apply makeup with a trowel. I don’t want to look like a clown.
I really appreciate any help folks can offer. Please, use small words and talk to me like I just came from Mars and have never seen makeup before. 
As a woman who wants to look like a woman, I feel your pain and confusion. I am also daunted when I walk into Sephora or Ulta and see the fifty-zillion-billion products, brands, etc. I’ve even had full makeovers at Sephora and come home with a boatload of product and still don’t feel confident that I know what I’m doing.
A good place to start would be watching YouTube videos. There are some incredible makeup tutorials on YouTube. (As always, there’s a lot of crap to wade through and weed out, too.)
Put this into a google search box:
cosplay makeup “male” site:youtube.com
If you just put in
cosplay makeup “male”
you’ll find other help besides YouTube.
Sorry, that’s all I’ve got at the moment. Good luck.
Yup, I’ve watched some of the videos, and they look pretty useful for technique. But of the ones that actually list the products they use in the notes, almost always when I try to find them they’re out of date. Plus, there’s no way to know if the colors that work for them will work for me.
In addition to the suggestions already made, search YouTube for “stage make-up,” “theatrical make-up,” female to male make-up." Those might offer some help and then check the recommended videos from those links.
I wouldn’t buy expensive make-up, especially if you need to practice. Any variety of Dollar Tree, etc. has basic make-up (eyeliner, foundation, eyeshadow, contour) that will save you lots of money until you figure out what works or what else you might need.
Good thought, though I’m not looking for stage makeup, which (at least if I’m understanding it correctly) is much more obvious and dramatic so it will look good under lights. I’m looking for something that will look good under normal day-to-day conditions at a convention or other cosplay event.
Good suggestion about practicing with cheap makeup, though!
Just sharing my own experience, as a woman who (once my over-active teenage hormones subsided) has never had any interest in make up. My idea of getting dolled up is a little blush and some eyeliner.
Occasionally, I’ve tried to do more with make up, because I do know that properly used it really can enhance one’s looks. But when I go “all out” - which for me involves mascara and a neutral lipstick along with the blush and eyeliner - I feel like a clown when I look in the mirror.
Objectively, I know I’m not overdoing it: I don’t use any foundation, concealer, eyeshadow, or large quantities of the products I do use. So I can’t possibly look like a clown … but the whole thing is so alien to me that I feel like one.
So, your personal reaction may not be the best way to judge. Ask a friend or two (or post before and after pictures here if you like!) to get more objective feedback.
Is there a cosmetology school near you? You could make an appt for a makeup session there and tell them what you’re going for.
I have a friend who is a drag queen. If I was going to try to do male cosplay makeup, he’s who I would ask for help. Do you have a drag queen friend who’d do reverse makeup with you?
The Dollar Tree, Big Lots, etc is a good idea. They don’t have the aisle after aisle of confounding vastness of choices that you find in other places. Walgreens has a cosmetology clerk who could steer you to to some simple, basic choices in the right shades. Go at a non-busy time of day.
Little girls with their mothers makeup. There is a reason it looks cute and funny: because it’s a real skill. You don’t automatically inherit the skill just by being 21 (or 31). You have to put in the time, and get feedback from other people.
From watching my sister try to do makup as an adult.
For color matching, places like Sephora sometimes have little machines that they will put on your skin that will tell you which color you need. A lot of brands have online apps to walk you through trying to find the right color, too.
I would suggest going to a Sephora, Ulta or Mac counter and telling them what you told us here. Write down notes. You don’t have to buy anything, but they can lead you through it. Some stores have return policies if the color doesn’t match you.
Foundation really depends on your skin type. It can be radically different on different people (dry skin vs oily, etc). For cosplay, you want something that is long-lasting. You can prime your whole face with face primer to help things stay, and there’s setting spray on top of that. When you watch the tutorials, try to pick up what kind of item instead of the brand - for example, cream foundation versus powder, etc. Then you can try to find other similar items even if they are different brands. Or if they say an expesive brand, search “Expensive Brand Dupe of item” and you should be able to find good ones to try.
Since you are so new, I echo the others and say just try out as much as you can - it’s really all trial and error. NYX is very cheap and a good brand. BH has a lot of good cheap eye shadows. Colourpop has cheap eyeshadow, cheek and lip items.