Your No-Fail Guide to Becoming a Lipstick Person

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What lipsticks are the most reliably long-lasting?

Grasie Mercedes, TV host: "My favorites are MAC matte lipstick, Stila Stay All Day liquid lipstick, and NARS Pure Matte. All three are long-lasting, especially the Stila. It applies moist like a lipgloss and dries matte—it's incredible and seriously lasts all day."

Emily Amick, makeup artist: "I also love a matte look for my lips most of the time, and I always go for Make Up Forever Aqua lipliner. I cover my lips in the liner, and it stays on for the long haul. It's waterproof and highly pigmented. If I want it to look shiny, I'll just top it with a clear gloss."

Ashley Wheeler, talent assistant at Conan: "Most of the matte colors that I have from MAC are great for a long-lasting wear with minimal touchups. The Kat Von D Everlasting liquid lipstick is also exceptionally great. It's not the easiest to apply if you're not used to wearing lipstick, but it's by far the best in my collection."

Julia McLellan, musical theater performer: "One of my favorites is Revlon Just Bitten. It's an incredible stain that you'll have in place until bedtime. Whenever I can for performing, I use MAC lipstick in Rebel. It's such an amazing color that demands attention and makes me feel like a superhero. As you can imagine, I wear it a lot in real life, too!"

Sofia Hultquist, composer and founder of Drum & Lace Music: "My consistent number one has been Tarte Glamazon—I love the richness of the colors. If I want a more moisturizing lipstick, I sometimes use Laura Mercier Crème Smooth lip color. A recent long-lasting find that's a little tougher to use is Hourglass Opaque Rouge."

Chelsea Moylan, owner of Anomie: "I have a select few lipsticks that I term my "drunk lipsticks"—they are my warriors that will stay on through drinks, dinner, dancing, and whatever else I happen to get into while out on the town with zero worry and maybe one touchup, if that. Make Up For Ever Aqua Rouge (this basically won't come off until you scrub your lips with a Brillo pad the next day, so beware) and Nars Velvet Matte lip pencils and Semi-Matte lipsticks will all last you through a bottle of Chardonnay or a terrible case of food poisoning (I have tested this on several occasions, though not intentionally). Basically, go matte or go home...with terribly faded lipstick."

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How do you make sure your lipstick stays in place?

Sofia: "I exfoliate my lips in the morning with a toothbrush and moisturize with Lucas' Papaw Ointment. Then I line my lips with Bite Line and Define lip primer, use Make Up Forever Aqua lipliner as an allover base, and then put on lipstick."

Ashley: "I apply a thin layer of concealer, put on a bit of compact powder on my lips, outline them with a lipliner that's a close match to my lipstick color, and lastly, apply my lipstick. A matte lipstick is always my go-to for a long-lasting wear. I enjoy wearing gloss lipstick as well, but they usually take a bit more to maintain."

Grasie: "I first make sure my lips are moisturized, then I pat dry with a paper towel and line my lips with a lip pencil and completely fill them in. Then I apply lipstick and pat again with the paper towel. My final step—this is the fun part—is taking my index finger and putting it in my mouth and then pulling it out. Sounds dirty, I know, but it keeps lipstick off your teeth!"

Emily: "If you're cool with a matte look, dust some translucent powder over your lips when you're finished, or try an eyeshadow in the same color family as your lipstick. A good trick to make your lips look extra pouty is to dab just a little shimmer eyeshadow on the center of your lips. So sexy."

How do you keep it from rubbing off while eating?!

Chelsea: "Think about your food choice. I'll eat huge burgers with lipstick on, but sometimes the lipstick comes off on the bun. It's generally best to order food that requires utensils and can be cut into smaller pieces."

Sofia: "All it takes is being a bit more mindful of how you use your fork or spoon! It's just a matter of biting down with your teeth more so than your lips."

Ashley: "Finger foods are not usually a problem as long as they are bite-size and I'm able to pop them right in my mouth. Nothing bugs me more than when I take a bite out of something and lipstick ends up on my chin or nose. It takes a big bite to make that kind of smudge, but it happens and it's the worst!"

Julia: "Take smaller pieces of what you're eating when at parties so that the food won't touch your lips, and always carry a small compact with you so you can slip into a corner and check your lips after eating."

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What about drinking?

Grasie: "I pat my lips with a cocktail napkin before I drink a cocktail to avoid lipstick all over my glass."

Sofia: "If you lick the rim of the glass you're about to drink from, it will keep the lipstick from coming off onto the glass and will leave you with perfect lipstick. To-go coffee cups are definitely still a work in progress though!"

Ashley: "If it's a beverage that's appropriate to drink from a straw, I always use one. While drinking champagne or cocktails, I have to be a little more careful. I try to open my mouth a little wider to rest the glass on my bottom lip and avoid touching the glass to my top lip altogether."

Julia: "Try to continuously drink from the same spot on your glass so lipstick doesn't get everywhere."

And what about kissing?

Julia: "When you're on stage, you often have to kiss someone without leaving their mouth looking like a crime scene, so I gravitate towards stains. Apply your stain, wait for it to dry, and then apply gloss as much as you'd like to keep it fresh."

Emily: "If you know ahead of time you're going to be making out, prepare! Wear a neutral color or non-sticky balm, like Burt's Bees Kissable Color (it's nice and minty, too!). If you're dying to have red lips, coat them in a waterproof liner or a lip stain and forego actual lipstick. If the kisses are unplanned—and those are the best kind—then wear whatever you want! Any person lucky enough to make out with you won't complain about getting a little Rouge Dior on their face."

Chelsea: "I'm not a big kisser when I've got lipstick on, but Make Up For Ever Aqua Rouge would probably be the only lip product that could outlive a mistletoe makeout session."

Photo: Getty Images

What's your go-to lip trick for when you know you won't be able to reapply?

Sofia:: "I'll put on a good base layer of lipliner, and sometimes even put it on over my lipstick."

Emily: "I like to stick with neutral colors, so when they fade, it's less noticeable. If you know you can't reapply for hours, wear a shade that's similar to your natural lip color. Or just go with a gloss, which is much easier to touch up and usually doesn't require a mirror."

Julia: "My favorite thing to do when I know I'll be gone all day is to use a stain and just reapply balm over the top. The balm is clear, so you can apply it on the go without worrying about correct placement and the color is still kicking underneath doing all the work!"

How do you deal with chapping and flaking?

Ashley: "I'll often wipe my lips first with a damp towel to remove any dry skin and apply Chapstick to moisturize my lips. I'll then wipe that off before applying my actual lipstick. When I want my lips to feel as though I'm wearing Chapstick, but still keep the bold color of lipstick, I wear Burt's Bees Lip Crayon. It's not as long-lasting as lipstick, but it's a very comfortable wear."

Chelsea: "Flaking is inevitable with super dry, matte formulas, but it's the price you pay for long-lasting lips. Be triple-sure to exfoliate with a scrub before application! You don't want flaky dead skin to suck up all the color and make it look like you've got croissant crumbs stuck to your lips at the end of the night! I've been there. It's bad."

Emily: "I love using sugar scrub from Lush to exfoliate. You can literally lick it off when you're done scrubbing and it tastes like dessert...mixed with dead skin, but let's not think about that."

Any other lipstick advice?

Grasie: "Red is always a great lipstick color choice for the holidays but a bright, bold pink lip is also very festive and unexpected."

Julia: "To remove lipstick at the end of the day, put coconut oil on your lips and let it sit for a few minutes—it'll break down the compounds in the lipstick."

Sofia: "Make sure you know which lipstick shades work for you—cool vs. warm—and definitely be bold with color. Lipstick can add so much to an outfit and to your confidence. Also, lipliners make for great pens in time of need, especially with all those holiday cards you might be writing."