OK, when I was younger I hired a person to show me how to do really good makeup. I was in a band and since I was the only trans and really the only one brave enough we pooled our money together and I hired a woman to show me how to do makeup. She taught me day and evening and all kinds of stuff. I had to go back and show the rest of the band members how to apply the night, with a little craziness and overdone makeup.
No Youtube back then but definitely check out all the tutorials on youtube. A lot of them is what the lady taught me in the eighties. And practice makes perfect and now days, less is more and the more natural the better it looks trans or cis. Eye shadow, mascara and foundation is good, but too much blush and so on is way too much. I love the smoky eye look, more neutral but still reddish tinted lipstick and definitely match the foundation with your natural skin tone.