Choose the Right Color
"The general rule for reds is that the fairer your hair and skin tone, the more the orange-based reds suit your complexion," says Poppy King, creator of Lipstick Queen. "Pink-based reds are best for those with deeper skin and hair."
"Women with cool undertones should wear blue-based reds, while more orangey-brown shades will work on warm skin," says Collier Strong, consulting makeup artist for L'Oréal Paris. An easy rule to follow: If the veins inside your wrist look blue, your skin tone is cool; if they're green, it's warm.
Prep Your Pout
Smooth, soft lips are the best canvas for a matte red lipstick. (Try Smashbox Be Legendary Lipstick in Legendary, $19). "Gently rub lips with a warm, wet washcloth before you apply any color," says makeup artist Emily Kate Warren.
Bold lipstick will only highlight any cracks and cuts on your lips, so use a lip moisturizer with vitamin E to prevent them from drying out. Try Sally Hansen Full & Radiant Lip Definer, $9.55.
To increase staying power, coat them with a lip liner beforehand to prevent bleeding and to make the color last longer.
Apply It Right
For the most even application, let your lips go a bit slack when you slick on your lipstick. "Puckering too much makes it hard to get a perfect finish," says CoverGirl celebrity makeup artist Molly Stern.
For the most intense effect, apply your lipstick straight from the tube. "If necessary, you can use a lip brush to get the edges perfect," says Warren.
"If you want to wear lip liner with your lipstick (and you don't have to), apply the lip liner after you put on your lipstick to even the line, instead of before, when you are more likely to go out of the natural lip line," says King.
Maximize Its Wear
"Red lips can be arduous to maintain, so if you're too busy to touch up, use a long-wear product," suggests Strong. Lipsticks can be drying, so keep gloss on hand. Try L'Oréal Infallible Lipcolour in Beyoncé's Red, ($11), which comes with a hydrating topcoat.
Avoid Lipstick Teeth
Prevent migration with this trick: After applying the color, close your lips around a Q-tip and pull it out of your mouth, advises Warren. "It will remove the excess closest to your teeth."