1. Do border control. Before you apply, use a sponge to dab a powder foundation around the outside of the lips. It'll help keep the color from seeping outside your lip line and also create a subtle contrast that makes lips appear a bit fuller, says New York City makeup artist Maria Verel (who makes sure Diane Sawyer's lipstick looks great—in high-definition—by 7 o'clock every morning).
2. Forget the brush. "The color is more intense if you apply it directly from the tube, and the more pigment that winds up on your lips, the longer it will last," says New York City makeup artist Matthew Nigara.
3. Pencil it in. Once the color is in place, "tidy up around the edges with a pencil," says Verel. "It's drier and waxier than the lipstick, so it will create another barrier against bleeding." Choose a neutral shade that closely matches your natural lip color and is no darker than your lipstick (try one of these makeup artist favorites: Chanel Precision Lip Definer in Nude, Nars Lipliner Pencil in Borneo, or MAC Lip Pencil in Spice); for a line that looks natural, not harsh, use short strokes with the side (not the point) of the pencil.
4. Blot a bit. After you've applied the color, put a tissue between your lips and gently press down. "It lifts away the excess emollients that cause lipstick to smear," says Verel.
5. Protect your teeth. Red-carpet regulars and beauty queens may smear Vaseline on their teeth to keep lipstick from rubbing off on them; if you do it, though, you'll probably look as if you have Vaseline smeared on your teeth. Instead, after you apply lipstick, put your index finger in your mouth and slowly pull it out. (Feel free to Purell liberally first.) "It's the best way to remove any color that has migrated to the inside of your lips, which rubs against your teeth as you talk," says Nigara. Another preventive measure: Don't pucker up when you apply lipstick—it'll increase the likelihood of getting color on that area.