At the makeup counter
Let's face it, when you are growing up and greeted by a palette of eye shadow, the first temptation is to do a dash of this color and a smudge of that one, and then round it off with big black eyeliner and a bucket of blush. That's great if it is Halloween, but for most other days of the year, you will come across as a beauty products amateur. That was the same for me in the early stages of my transition. We need to be a little more prudent in what makeup we use and how we apply it.
We are not usually blessed with baby-smooth skin. Depending on genetics, hair growth, diet, age, and goodness knows how many other factors, trans women often need heavier foundations, concealers, and powders. The first brand I used was Dermablend, which worked wonders in giving me a natural base to work with. (It's also great for hiding scars, spider veins, and even tattoos if you need to.) As my skin got smoother through permanent hair removal and hormone therapy, I could switch to lighter combinations. These days, unless it's for cocktail-dress occasions, I'm often happy with a good pressed powder from Sephora.
The next lesson I learned was that earth tones are your friend. Sure, it's great to be experimental with brighter colors, but I always found it a double-edged sword. Did I want people to be wowed by my makeup or not? Yes, it's great to be admired, but I soon realized that in my early stages of transition (when my insecurities were at their height), I preferred to blend in and not stand out. So that meant going easy on the glitter and opting for more neutral tones. Some trans girls were a lot braver than I was at the time, and they went with whatever makeup styles they wanted. But I preferred to be inconspicuous.