Last week I got myself a tape measure, figured out some sizing things and ordered a cheap dress online. It looked good, and for the first time in my life I felt beautiful. I felt like I could actually pull of a transition and not look like an ugly man in a dress. I giggled and cried and it felt so good. The next day I went to the mall, got my ears pierced, bought all the girly things I was brave enough to in person. Then I paced around mac like a weirdo until I worked up the courage to go in and ask for help picking makeup. They were great and super helpful getting me some basics. When I went home, I put my dress on, and thought I’d take it slow and just put on some lipstick and paint my nails. When I saw myself, I felt like an ugly old man in lipstick, and it fucking ruined all the euphoria from before. I know I can get past that, do my makeup better and find something more comfortable, but I wanted to hang on to that feeling forever. I saw the woman I know I am inside for a moment and wanted the rest to just happen. It’s not gonna be that easy though, is it?
Another cis woman, and my advice is similar. As the previous comment says, lipstick on its own is way harsh on anyone! Hold off on lipstick (try some lip gloss instead! You presumably missed out on the lip gloss era of your childhood that many girls go through after all) and for now maybe focus more on the eyes, specifically eyeshadow and eye liner. As far as makeup goes these are relatively gender neutral compared to say lipstick or mascara, so they might be less dysphoria-triggering. Check Google images for searches along the lines of “men with eye makeup” and you’ll find a good spread of masculine, feminine, and gender-queer inspo. Generally I recommend makeup newbies (with light or mid-tone skin) start with neutral tones for eyeshadow: a medium brown, a dark brown, and a gold or copper for some fun. For eye liner pick something in the browns: a little lighter if you have light hair and a little darker if you have dark hair. Black can be really harsh unless you have black hair, and navy and other colors are expert-level makeup. If you have darker skin, however, it’s actually easier to jump into bright colors because you’re working with a dark “canvas,” which makes for better contrast. Not to say that blue, purple, and green are off-limits for light-skinned folks, but you have to worry more about skin tone clashes so it’s trickier than sticking with neutral colors at first. Reds and pinks are intermediary difficulty and a good first color to play around with. Regardless of color start with a light application; like the other comment says, you’ll look unbalanced if you apply one element of makeup heavy without applying everything heavy. Also it’s really common to get bad advice at the makeup counter, so while they can be helpful in guiding you if you’re completely lost, take what they say with a grain of salt and trust your own judgement of what looks good. Also keep in mind they can only recommend what they stock; as an example I’ve needed to bring my own eyebrow powder before when having my makeup professionally done for a special event because too many times I’ve found anything other than one specific shade from one specific company looks really weird on me.
Tl;dr: don’t despair, makeup is hard
This is really helpful, thank you!