Where to start?
We've noticed that the most frequently asked questions, in the various on-line support forums where we hang out, are the ones from rank beginners. If you're just starting out, all of this is probably overwhelming. So we thought that we'd put our answers to all those questions in one place. We'll be adding on to this collection of tips regularly, but we're going to start with the subject of the most askeded questions...
Makeup:
You may want to get at least some idea of what you like and how to get there. YouTube offers a bewildering array of trans-related makeup lessons and tutorials. Some are gems, and some are worse than useless. You'll see what we mean. Stay away from the videos aimed at drag queens, unless that's the look you're going for, in which case you might want to stop reading here. YouTube built their business around figuring out what we want to watch and giving it to us, so as you hop around almost randomly, the service's algorithm will refine the selection, as if by... magic. Plan on spending hours there. No, really. When your brain is full, it's time to gear up and get in lots of practice to master your "look".
Also, if you've identified a particular product you'd like to learn about, chances are that the manufacturer will have posted an entire series of videos about that very thing.
Another approach is to pay for tutorial's or lessons. These are available from most of the big name cosmetics chains, but Sephora staff are specially trained to deal with the unique needs of transgender women, so you could just wander in and ask about this or that type of product and get excellent suggestions, but their "Beauty Lesson" will give you a running start, if you feel that that's what you need.
Aunt Kelly's Three Keys to Makeup Success
Tools, Product and Technique. Success will come when you identify the combination of the three that works for you. As you practice, you will discover what works for you, and what does not. We cannot overemphasize the value of that practice. It is through practice, trial and error, that you will identify the combination of the three keys that works best for you.
But here are a few tips to get you started...
Tools:
We're talking brushes and sponges.
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Brushes: Use this search link to go to amazon.com. Pay attention to the reviews and spend no more than $30. Eventually, as you refine your technique, you may want to add something more specialized, like a small angled brush for fine work, or a kabuki brush for foundation. This is where you might want to spend a little more.
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Sponges: You'll want two kinds, wedges and a beauty blender. The links point to Amazon, but these are available at your local drug store or supermarket as well.
Product:
- Foundation: Do yourself a favor and go to Sephora, M.A.C., Ulta, etc. and let a pro do a color match for foundation. Let them know what your budget is so that they can suggest appropriate products, but be prepared to spend more than you would on drug store products. You'll save money in the long run by avoiding the guesswork and poor choices.
Because I know someone is going to ask, I use Bare Minerals Loose Powder Foundation, in the matte finish, because it works for me and the technique I've developed. Your mileage may vary. Your local Ulta store carries the Bare Minerals starter kits in an assortment of shades. As an alternative way to try out loose powder foundation, this kit from Sweet Face Minerals, is an excellent value. It even includes a short kabuki brush, perfect for use with loose powder products. - Color Correction: If you have any kind of beard shadow, or areas of significantly differing pigmentation, you're going to want to learn about color correction. This video covers the subject as well as any other that I've seen. Mind you, I'm not keen on Nikkie's eye makeup later in the video, but that's just my old lady sensibility. At any rate, she's a great teacher and everything she shares will be of at least some value.
Speaking specifically about beard cover, you will find that there is probably more debate about this area of makeup for TG women than anything else. When you have a spare hour or two, crossdressers.com has a (very) long running thread on beard cover.
FWIW, I use the L.A. Colors Pro Concealer Stick in 615 "Pure Orange". My beard shadow is pretty light, since much of it is gray, and because I'm part way through electrolysis, so I have to use very little, blending carefully to avoid those sharp color demarcations. - Concealer: Use what works. There are a number of drug store products that, IMO, work just as well as anything from the specialty stores, so some experimentation is easily affordable. I've landed on two products:
- Maybelline Instant Age Rewind, and
- Loose Powder Concealer
Again, these are what work for me. I offer them as suggestions for two different types of products and application methods.
- Mascara: I've tried dozens. IMO, the point of diminishing returns is around $10-$12, so feel free to experiment a bit and find what works for you. I have rather short lashes, so I like Maybelline New York's "Lash Discovery" because it has a brush with shorter bristles. Unless you need it, stay away from waterproof mascaras.
- Eyeshadow: This is another area where personal tastes vary wildly. All I will say is that, for the love of God, no green or blue! Again, I've not found a huge improvement in quality/workability in more expensive lines, as long as we avoid the super-cheap, off-brand offerings.
- Brows:
- First of all, if you haven't had them waxed or threaded into shape, start there.
- Because I'm lazy, I use a Finishing Touch Flawless Brows trimmer in between waxing/threading sessions. There are also very inexpensive manual "facial razors" that are made just for brow maintenance.
- Pencils: The eyebrow pencil is the OG product and will still get the job done. As with all brow products, pay attention to color. Most beginners will select something too dark for their complexion/hair color. The "next generation" pencils are marvelous. They usually have a shaped tip, require no sharpening (sort of like a mechanical pencil), and also feature a small "spoolie" brush on the other end.
- Pomades: Eyebrow pomades are a bit trickier to use, but are just the ticket if you have some gray in your brows.
- Stamps and stencils: More trouble than they're worth, IMO. They're great, if your alignment and application is perfect. If you goof, you're starting all over.
- Eyeliner: This is another area where personal preference, in both technique and product, varies wildly. Some exerimentation is definitely in order, but in general, pick a product that makes it easy to achieve the look you're going for. Products designed for a "smokey eye" look won't work well if you're after a sharp line or "cat eye" extension, and vice versa.
- Contouring: Hard to go wrong here. You're looking for a palette with an assortment of shades (at least two). I'm still using an inexpensive 2-color pallette by NYX.
- Blush: Yet again, feel free to experiment with inexpensive products. Better yet, pick one of the many multi-shade palettes. When you find something you like, you'll probably be able to buy just that shade when the time comes.
- Lips: Matte, shiny, or wet look? Pink, purple or black? The sky's the limit here. Like any woman who uses lip color, I have a ridiculous number of lipsticks, of which I use only two or three with any regularity. Diminishing returns comes in around $10 again, so you can afford to experiment with both color and finish, even the long-lasting lip "stains". The one exception in my makeup case is the Merle Norman "Lip Pencil Plus". Available in a huge array of shades, it is a double-ended pencil with lip color and liner at opposite ends. Very handy.
Technique:
This is where it all comes together. As you progress, you're going to find that this or that product or tool is best suited to both the look you're after and the technique you've developed. How do you get there? Practice, practice, practice.
Clothing:
Even more so than one's makeup "look", fashion is a matter of personal taste, or lack of taste. Let's be clear... You should wear anything that makes you feel good about yourself, but if your goal is to be recognized and accepted as would any cis woman in similar circumstances, you need to dress the part. That means selecting clothes that women of similar age would wear in the venue you plan to visit. Pay attention to what women are wearing; at work, in the supermarket, at the theater, etc. Trust me, they do
Some visual aids...
OK: 
Not OK: 
Unless it's just after work, nobody shops in a business suit and pearls. And unless it's Walmart, nobody ever shops wearing a neon pink mini skirt. Yes, that's an extreme example, but you get the gist.
Compared to that of men, women's fashion offers an incredible array of choices, and as long as you keep in mind that your age and the venue dictate what is "normal", there's still a staggering opportunity to express yourself.