Before even attempting to pick out a color make sure you exfoliate and brush your lips with a toothbrush for the smoothest possible finish, wipe them down with a washcloth to remove excess flakes of skin. Hydrating your lips is crucial to this process because a moisturizing treatment is the key to smoothing down any wrinkles and lines you may have on your lips (use a thick lip balm without a drying agent/alcohol in it).
Regardless of which lipstick you choose, make sure that the formula is sheen/sheer because matte lipstick formulaas will get creased on your lips in every line and groove and make them appear dryer than they really are. Cinnamon and mint-flavored lipglosses and lipsticks will provide a plumping effect because the ingredients will cause a swelling reaction on your lips. Sheen and shimmer will also make your lips appear larger than they really are because it helps the light reflect in a way that creates a fuller effect. If you want longevity to your lipstick, make sure you fill your lips in with liner before you add your lipstick on top and then finish it off with translucent face powder, this is the trick makeup artists use to have lipstick last long periods of time.
Red lipstick will complement all skintones
Choosing your lipstick color depends a lot on your skintone. If your skin is a pinkish hue then you want to choose blue-base red colors (not orangey, warm tones like your skin) and the opposite is true for olive skin, choose an orangey red (not the blue-based red which is cool toned like your skin). This contrasting effect will allow the red to make your teeth appear whiter. The deeper and more opaque red you pick, the better for creating a tooth whitening effect. But red lipstick easily can get on your teeth, thus diminishing the purpose of wearing it, so make sure you press a kleenex between your lips before you're done with the application to remove any excess, loose lipstick. If you leave extra lipstick on your lips it also will make your lips appear chapped and uneven instead of that glossy finished look you're going for.
Pink tones bring out the yellow in teeth
Mauve-based lipstick is also a good option to try if you're scared of doing the ultimate red lip. For real precision you will want to do your application either with surgically-steady hands or with a lip brush because strong colors like red must be applied perfectly in order to look good - any mistake will be readily visible. Whatever you do, if you're looking to whiten your teeth, do not wear pink lipstick, especially if you plan on doing a lot of laughing or talking. Pink lipstick will bring out the natural yellow in the enamel of your teeth and definitely showcase your plaque if you have any. You can feel safe using pink lipstick only if you have just returned from the dentist to have a deep cleaning or if you've recently completed a whitening regimen.