I wear makeup everyday, but most people don’t realize, so I think that I must manage the natural look pretty well. The primary reason why I even bother is because I have terrible skin, and I am allergic to the skin products that actually work on me (like benzoyl peroxide).
When I met my husband in college, I wore concealer, pressed powder, eyeliner, and lipstick everyday; and if it was a special occasion I added eyeshadow, mascara, and foundation. It took him three years to get me down to just the concealer and powder for everyday, and he’d love it if I’d drop those too.
I’m surprised that no one has actually mentioned powder yet - as long as I use that on top of concealer, there’s little reason for foundation. Admittedly I have more than average sensitive skin, but I couldn’t possibly wear that everyday without turning into one giant pimple that covers my entire face. (And yes, I’m including the oil-free, fragrence-free, hypoallergenic ones in that statement - you can’t wear a foundation without blocking pores in your skin, it’s as simple as that.) It also takes an expert to apply in such a way that it looks natural in direct sunlight.
Make sure your skin is clean and not oily. I like Purpose soap - it’s very mild. If your skin is at all dry, even just in parts or just today, use a moisterizer next. I like Biore’s water based facial moisturizer, as it helps without ever feeling like it’s even on your face, even considering my very oily skin. Use a matte concealer that matches your skin tone very well, and blend well. Then use a high quality loose powder with a smooth finish, applied with a large standard brush, blending down the neck a little. (It took me many years to figure out that despite the inconvenience, loose powder does a better job and stays far longer than pressed powder. Though pressed powder is still fine if you need a touchup during the day.)
For special occasions, I use mascara (as already mentioned, use brown-black unless they’re naturally black already; I’d also avoid the ones that add length or fullness unless you want to look like a clown). For eyeshadow, shades of brown, non-sparkly, will define without being very noticable on most people. If you want to use eyeliner as well, stick again with a dark brown, and very carefully smudge it so that it’s not a harsh, obvious line. (I’d recommend practicing beforehand, because smudgeing well is a lot harder than it looks.)
There are thousands of lipsticks available of varying degrees of sublety, and it should be fairly obvious from the packaging how bright and shiny it’s going to be. Pick whichever color matches your outfit as long as it’s going to look good with your skin tone. Just don’t pick something shockingly bright red and glossy and with sparkles and stuff if the rest of your makeup is fairly subtle. You really need to know what you’re doing for that to work. The alternative, which is what I use unless it’s a really special situation, is a colored lip gloss. The effect is muted but still adds a bit of color to the overall effect, and they’re now readily available in a number of shades.
Hmmm… what else? Despite my earlier rant, foundation is acceptable for special occasions and going out at night - just be sure to pick out a very good skin color match and blend well, all the way down the neck. Concealer goes underneath, and powder on top. Also practice this one beforehand. You may have to try several brands to find one that matches your skin’s texture.
I’ve never quite seen the point of blush or lip liner, but I guess YMMV. I used to feel like a clown with them on, even in the days of my very heaviest makeup.
Keep your eyebrows plucked - into a natural shape is perfectly acceptable.
And always, always, no matter what, wash everything off before you go to bed at night.