I've noticed that a majority of my lipsticks are in the brown color family. I'd like to wear something that has more red in it, but I feel like my choices are limited because anything I like is too bright. Should I just stick to wearing and buying lipsticks with brown undertones?

If you feel that red is too dark, try a gloss. Gloss is great because it's a sheer version of the colors you want to wear. Also, soft pinks are a great way to brighten up your skin tone. If you want to experiment with colors, your best bet is to go to the drugstore and by some gloss palettes. Revlon makes a few and Almay has some great colors in their Whipped Gloss line. It's a great way to be able to try the colors you want without it being a major investment.