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Q: How can I keep my lipstick from fading? I found a shade I love, but it won't stay on.
A: I'll tell you in a second, but first I'd like to share what the ancient Greek philosopher Heraclitus told his wife when she complained about fading makeup: "Everything flows and nothing abides," he said dolefully. "Everything gives way and nothing stays fixed." Okay, so he wasn't really talking about makeup, but you get the point, right? Life is so much easier when you go with the (impermanent) flow.

But there is a way to make your lipstick last at least through a passionate conversation and maybe even a couple of cups of coffee. Dab a bit of foundation over the lips and lip line, which helps to fill in fine lines and gives a lipcolor something to adhere to, says makeup artist Sonia Kashuk. Next, with the side of a lip pencil rather than the point, outline your lips, says makeup artist Rebecca Restrepo. Using the side gives a softer application that's easier to blend; look for a natural or nude shade that matches the color of your lips. (Restrepo likes the Prestige waterproof lipliner, $5.50; Ulta.com.) Then apply your favorite lipstick.

Keep in mind: The glossier or sheerer the lipcolor, the more quickly it will fade.

Keep reading: How to find the perfect lipstick 

Q: How can I keep my lipstick from feathering?
A: I emailed makeup artist Sonia Kashuk, who I'm sure has never had a feathered lip in her life, to ask her how she prevents such things. "HELLO DEAR!" she said. (She always writes her emails in caps and uses lots of exclamation points. If you didn't know her, you'd think she was very loud and excitable. She's just the opposite.) "I ALWAYS USE A FOUNDATION OVER THE ENTIRE LIP," she wrote. "THEN I LINE THE MOUTH WITH A NEUTRAL OR COLORLESS PENCIL."

Bottom line: A colorless lip liner will prevent feathering and will work with any lipstick shade.

Q: I've tried every kind of mascara; nothing stays on my lashes. What am I doing wrong?
A: No matter how sophisticated, glamorous and pulled together you are otherwise, there's no question that raccoon eyes will make you look either just plain sloppy or deeply psychotic. Your problem might be that you're applying too much eye cream, or that it's too close to your lashes, or that you're not allowing enough time between the application of eye cream and mascara, says makeup artist Pati Dubroff. Be sure to apply eye cream only under your eyes and on the ocular ridge just below your eyebrows, says makeup artist Ross Burton. He suggests coating lashes from the base upward, because if you apply mascara just on the tips of lashes, it weighs them down and the product can slip onto the skin. You can also try a light dusting of loose powder on your eyelids, even getting a bit on your lashes to hold the mascara, says Dubroff.

Bottom line: Ease up on the eye cream, apply mascara from root to tip, and try a water-resistant version.

Q: How can I find a neutral shade of lipstick that looks good on me?
A: I went straight to the queen of neutrals (and celebrity makeup artist), Bobbi Brown, for an answer to your question, and I'm glad, because as usual, she was full of surprising information and happy to share it. I asked her to please give advice about which neutrals look best with which complexions and haircolors. "It's a fallacy that you should choose a lipcolor based on your skin and haircolor," she said. "What matters most is the natural color of your lips." At this point in the conversation, I said what I always say when Bobbi tells me something that never occurred to me. "Really?" I said, as if it couldn't possibly be true. "Yes," Bobbi said patiently, "and that's why if you try on a lipstick that looks beautiful on a friend—even a friend with a similar complexion—it might not look as beautiful on you." Some women have very red lips, some have pale pink, and the same lipstick will look very different on both. When you're shopping for a neutral, don't wear makeup, because a shade that looks great without makeup will also look great with it.

Try on lipsticks in daylight, says Bobbi, just as you would if you were trying on a foundation. And never choose a neutral that's lighter than your lips, because that will make you look washed-out, she says. Really.

Bottom line: To find the perfect neutral, look for one a shade more intense than your natural lipcolor.

Keep reading: 4 steps to luscious lips

Q: I have a faint, dark discoloration on my upper lip; what is it, and how can I get rid of it?
A: My six least favorite words from any doctor: "I don't know what this is." Lucky for you, Deborah Sarnoff, MD, clinical associate professor of dermatology at New York University Medical Center, has some ideas about what might be causing your problem. It may be hormone related: Circulating estrogen, either your own or from estrogen replacement therapy, when combined with sun exposure, can cause the kind of discoloration you describe. Or it may be caused by inflammation on your upper lip if you've had acne or a hair removal treatment (like waxing or tweezing), which can cause darkening of the skin when exposed to sunlight, especially in people with darker skin.

Bottom line: A cream containing hydroquinone or kojic acid (such as La Roche-Posay Mela-D Dark Spots, $45) along with a topical retinoid (like prescription Renova) and mild over-the-counter hydrocortisone cream can fade the discoloration after about six weeks of nightly use. But nothing will work unless you also use sunblock religiously.

Q: My sister-in-law says older women shouldn't wear red lipstick. I like to wear it because it makes me happy. What do you think?
A: It makes you happy? Then here's what I think: The medical profession's oath, Primum non nocere (first do no harm), is a good bottom line for all beauty concerns, including this one. Are you hurting anyone by wearing red lipstick? I don't think so. So in the words of makeup artist Julie Hewett, "You go, girl. Get your red on!" (I would never talk like that, but I'm glad to let Julie do it.) Here are her ideas for making the most of your red lipstick experience:

Find the right shade. If you're fair, choose a blue-based, cool crimson; if your skin is olive, try an orange-based, fire-engine red; and if you're dark-complexioned, wear a deep, burgundy red.

Apply it right from the tube (instead of using a brush); to prevent the color from bleeding, use a lip pencil after you've applied the lipstick.

A red mouth looks most chic when you've evened out your complexion with foundation and you're sporting a couple of coats of black mascara.

Bottom line: You like it? You wear it!

Keep Reading: The step-by-step guide to bold lips

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