"Applying gloss over your lipstick is a common mistake," says King. "This can cause the lipstick to bleed and transfer onto the teeth."

If you're going for more sheen on the lips, King recommends applying a lip balm first (as discussed in Rule No. 2) -- not a lip gloss. Or, instead of lipstick, opt for a highly pigmented liquid lip color, such as Nars Lip Gloss, $26.

After your lipstick is all filled in, sometimes the edge still looks a little wonky. To fix this, King suggests applying liner after your lipstick to even things out -- without going outside the edge, of course. "Often it's easier to line after lipstick application," she says, since you already have the basic shape to work with.

If you're still worried about your lipstick bleeding outside the edge, King recommends using a lip brush to apply concealer around the lip line, or doing the same with a colorless lip pencil, such as Lipstick Queen Invisible Lip Liner, $10.

Matte lipstick is classic -- and classically temperamental. Matte textures are the most drying, making exfoliation and hydration of the utmost importance. But matte lipstick also fades and rubs off more easily than other products, which means eating, kissing and even rubbing your lips together are off the table if you want to maintain a perfect pout.

"When you rub your lips together with a matte stick, it breaks the color down and ruins the Cupid's Bow shape," explains Blair. "Cream lipstick better stands up to rolling the lips."

If that all sounds a little high-maintenance for you, Smith says you can still achieve a matte finish and longer wear by dusting a translucent powder over cream lipstick.

A word on color: According to Blair, "The closer the product is to your skin tone, the more natural it looks." That goes for reds, pinks, oranges, nudes and everything in between. For example, if your skin has warm undertones, like yellows or reds, a warm-toned, rosey-pink lipstick will look more natural than a bluer pink -- and vice-versa for someone with cool-toned skin.

So, if you're concerned that a certain color will look too bold, opt for a shade with undertones that match your skin.

"Wearing a lot of eye makeup with a bold lipstick can be too much," King says. "When wearing a bold lip color, try to minimize your eyes."

To strike the ideal eyes-lips balance, King recommends applying your lipstick first, then your eye makeup. This way, it becomes much easier to tell when enough eye makeup is enough, she says.