|Source: Wiscombe Art|
The easiest trick of all is to simply choose a color that's about two shades darker than the natural color of your lips. According to Bobbie Brown, these are the most natural and flattering shades. Head to a makeup counter where you can test out lipsticks, apply the color to one lip only, and compare. If it's a shade or two deeper than your bare lip, you've found a great color! Even if you plan to find a great lipstick at the drugstore or somewhere else you can't try them out, I'd recommend doing this first. You'll know what shades to look for.
Simple, right? If you want to try other colors like red (which, trust me, nearly anyone can pull off red lipstick), different shades flatter different skintones.
If you're fair skinned, look for pink, berry, and red shades that have some blue-ish undertones. If you want to wear a neutral, try to find a peach color with a pink undertone. Loud pink shades should be avoided.
If you have a medium skintone, shades with yellow undertones will look better. You can wear deep reds in addition to pinks with brownish undertones. For neutrals, you can even wear warm brown shades. Just make sure to avoid super pale browns.
Those with dark skin look good in deep reds with blue undertones and dark plum or even purple shades. Again, pale beige colors should be avoided.