Hi, and welcome to Susan's!
I am no expert, but I will give you my 2 cents. Skin tone is one of those really difficult things to do. Unfortunately, though there are tricks, the only way to really learn what looks right on you is through trial and error. Some shades look good, but then don't last. Some last but uggh! Some blend well into your natural skin color without the opaqueness you will need.
My suggestion is to find a way to do a makeover. Be sure and ask lots of questions. I was lucky to find someone who took me under her arm and showed me how to get a good look using off-the-shelf Cover Girl stuff available at Wal-Mart. She was really good and I would not trade that experience for anything. She gave me my colors and she was right. Yes, it did cost, but it more than made up for it in the amount of stuff I would have wasted otherwise. Plus the confidence of looking your best is worth every penny. I use some nicer stuff now, but I know how to work the cheap stuff too.
I did start with going to a dollar store. I got a bunch of cheap colors of stuff for a buck apiece and began to experiment, figuring that I would get the best color in a decent brand when I graduated to bigger and better things.
One other thing that will help you is to learn to shave very closely first. It is a lot better than trying to hide any shadow. In short, exfoliate your skin first, so that it will be its smoothest. Then get a good multi-blade razor. I like the Gillette Fusion, but this is a matter of personal taste. I also like to use Noxzema Hair Minimizing shave gel. It really does work and helps keep your shave close for longer. Be sure to use a good moisturizer afterward. I like Aveeno Positively Radiant with sunscreen. Again this is a matter of your personal choice.
In short, smooth face, right color, and the rest will come.
I hope something in this makes some sense to you.
Best Wishes,

Kristi