First and foremost, You must be able to recognize what kind of skin tone you have. Knowing whether you have warm undertones or cool undertones is key to not just the right lip color but for all beauty decisions.
To find your skin tone: look at the inside of your forearm (in good lighting) If your skin looks orangey/yellowish you have warm undertones. If you skin appears pinkish/bluish you have cool undertones. If you are having trouble still, check out your veins. If you are warm you will have a greenish tint to your veins and if you are cool, your veins will appear more blue/purple.
Once you have established whether you're warm or cool you can start to pick the right hues for yourself. If you are warm, you will look best in orange-reds and corals. If you are cool (like myself) you will want deep rich reds and purplish reds. A little side note: The more "cool" undertones your lipstick has, the whiter your teeth look.
I have to say though, right now there is a plethora of fun lipstick colors available. It's good to stick to these rules, but loosely. Don't be afraid to try out a new color because it doesn't fit your skin tone requirements. Have fun and take risks :) The other great thing is, if you don't like the color after a couple uses, almost any cosmetic store/department with refund you!! There is really no risk involved :)
Here are a few of the red lipsticks I've been playing with lately
P.S. How cheesy are these pics? Sorry, I'm lame :D
This one is Maybelline ColorSensational "Red Revival." I bought this one at a Dollar Tree and I think it is my favorite. It has a slight shine to it and is super smooth. It also doesn't bleed like a few of the others do.
The second one is Jordana Matte "Scarlet Red." I bought it at a Food 4 Less for $1.19! Talk about a deal and in such and unsuspected place! This one is a very rich red but doesn't stay on as long as the Maybelline.
The third lip color is Wet n Wild #519A.... apparently color unknown :D I bought this at WinCo, (I find make up in the weirdest places) it was only a buck! Again, I like the color but this one rubs off quicker and bleeds slightly.
The fourth color is L.A. Colors "Luscious Wine." I picked it up at one of the 99 cents only stores. It goes on really smooth and is almost as rich in color as the Maybelline.
Lastly, this one is more of a magenta than a true red, but I like it just the same. The brand is Black Radiance "Queen of Hearts." I picked it up at a Rite Aid and it is part of a cosmetic line for African American women. I love how vibrant the color is and it lasts quite a while.
All in all, I love all of them, especially since none of them cost over $3.00 a piece! I urge you to try out a bright red if you haven't. Red lips instantly make you feel more sexy!! ;)
For more color choices:
Here is a link that shows a variety of Red lipsticks and categorizes them by undertone http://www.lhj.com/blogs/ladieslounge/2011/01/12/finding-your-perfect-red-lipstick/