Sammy,
I have seen advertisements on TV about one of these drugs stores where you can try a new lipstick for color and return it for a refund if you don't like it.
It was a major market chain.. maybe someone will recall the name.. but I THINK it was CVS. You COULD ask one of the local branches.
Personally I think you would be BEST suited to go to to a make-up counter at high end stores and have the women/men there give you some hints about what colors best suit you, and help you choose colors that both look good on you and make you feel good.
For example, really vivid red looks good on me, but I am not always very comfortable wearing it in the work I do. LOL

At any rate, having a professional help you choose colors is better than "trouble shooting" what you THINK looks good because YOU like the color. Think about the number of women out there you have seen who look like clowns because they didn't know how to make the right choices of color for their skin tones and didn't know how to apply what they were using anyway.
Lastly, what looked good on you at one age, doesn't continue to look good on you at other ages. Your skin changes, your coloring changes, etc.