Choosing a lip color is one of the most daunting things I think a woman can go through at the makeup counter. The truth of the matter is there are hundreds and hundreds of shades and textures of lipsticks and lip glosses and even lip pencils. The bitter truth of the matter is it's kind of trial and error. If you like red lipstick, you have to try on a bunch of different red lipsticks to figure out which one looks best on you. If you want a pink one, you can try on different glosses, different lipsticks and kind of see which texture works, which one lasts the right amount of time.
One fun tip to picking out something natural is to open up the bottom lip and look at the color that's inside your lip and match it to that. That will give you the most perfect natural pink that's going to match your coloring the best. I know it sounds crazy, but it actually kind of works.
If you want to wear your lipstick and your gloss together, you absolutely can or you can wear lipstick alone or you can wear gloss alone. There are so many different combinations out there for you to try. Some people like sticky glosses. Some people like watery glosses. I know that I like a matte lipstick. I don't really like glossy lipsticks. It's really a personal preference and what you're comfortable in.
I encourage you to go and try on as many as possible and see what you feel comfortable wearing.