Hello!

I’m 37 and have been experimenting with makeup since probably age 16. And I still am learning new things all the time, the world of cosmetics (even dermatology for that matter) can be incredibly overwhelming.
I feel there are two buckets when it comes to makeup. One is the “colors” – liners, shadows, mascaras, lipstick. The other is “face” including concealer, foundation, finishing powders, blushes, etc. I have unusually-colored skin somewhere around “Sallow” and “Olive”

and tend to have dark circles around my eyes (which I believe is due to off-and-on sinus congestion, but that’s another post!) So this blotchy skin tone of mine prompted me to look into foundation in my teen years, and I was determined to find something natural!
I played around with different “color” products – trying all manner of eyeliners/shadows and lipsticks. After 20 years of experimenting… I generally go with MAC lipsticks and eyes. If you are new to the world of cosmetics, perhaps start with just a little mascara and a good lipstick, maybe a little cheek color. Start easy and build up as you like. No rush! The MAC counter at your local dept store would be happy to try some on for size. Oh actually Avon makes some good stuff – including a lip “glaze” that I really like too! I think that even stuff in the drugstore may be appropriate to experiment and try some on for size without shelling out a lot of $… there is somewhat of a difference in quality for say, the shadows, but mascaras can be fairly similar (IMHO).
My biggest issue has always been a natural “face” and I’m willing to pay more for the right product. I’d never find that in the drugstore. The right product, for me, is very clearly Bare Escentuals; there is hands down no comparison in my book and I’ve tried just about everything including other brands of mineral makeup! They also are soothing to the skin and will not aggravate or cause acne. Their products already have SPF built in too, but I always put on a daily moisturizer first with a ton of SPF.
As far as breaking out… there are so many things that could cause it and the important thing is to ensure your makeup (or lotion, or anything) doesn’t cause or worsen it. Stress, hormones, surface bacterias, so many things lead to it and while a visit to the derm is a good idea, even they might not be able to solve it. I wish you all the best.
For me, an ongoing concern is also animal rights. I have to avoid using something they test on animals. Lately I’ve been buying soap that is tallow free, since tallow is actually beef fat! Tallow-free soap is not that hard to find, and the olive oil or lavender Italian ones (like from TJ Maxx and Marshall’s) are awesome. My skin has never felt so good, I don’t even need body lotion anymore!
Good luck and God bless!