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How to master the art of lipstick (that stays put all night long)

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How to (finally) master the art of lipstick Ezra Shaw - Getty Images

Lipstick is make-up’s ultimate mood-booster; it can convey energy, agency and vibrancy, signify power and seep sensuality. “Lipstick is happiness in a tube,” the inimitable make-up artist Charlotte Tilbury tells Harper’s Bazaar. “Your everyday nude, your prettiest pink, your iconic red – they can all make your skin brighter, teeth whiter, eyes sparkle and confidence grow.”

But lipstick can intimidate, too. For the uninitiated – or those who have had bad experiences (from transfer onto teeth, to an uneven fade) – lipstick requires a little know-how to execute effectively. Which is why we went straight to the best for advice; there’s nothing Tilbury doesn’t know about mastering the art of lipstick.

“Throughout my 30-year career, working with supermodels and stars on runways and red carpets around the world, I have always applied the same magic lip routine as I do on the face – ‘prep, perfect and then beautify’,” she shares. And, as you've probably guessed, it starts with skincare.

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1) Prepare your lips for lipstick

“As I always say, you can’t have a beautiful painting without a beautiful canvas,” Tilbury reminds us. So, before starting any make-up, her top tip is to apply an intensely hydrating lip conditioner with the moisture retaining ingredient hyaluronic acid – “creating a smooth canvas for velvet soft lip liner and lipstick application that lasts”.

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Lexie Moreland - Getty Images

2) Use lip liner as an outline and base

“Lip liner is the secret to defining your lip architecture and cheating lip symmetry – everyone always has one side slightly bigger than the other,” Tilbury explains. “I like to use my lip liner as a stencil, then go in with one of my lipstick. It makes your lipstick last longer.”

While there are many ways to apply lip liner, depending on the look you’re after, for the purpose of perfecting lipstick, Tilbury says to “always draw just outside of the natural lip line for fuller, wider-looking lips”.

And, to ensure longevity of your lipstick, “lightly feather the lip liner over the lips before applying lipstick – rich in waxes and oils, my waterproof formula prevents smudging, feathering and transfer for a kiss of colour that lasts for hours”.

3) Apply your lipstick

Now you can apply your lipstick, ideally in a matching shade. Naturally, Charlotte recommends her new Hollywood Beauty Icon Lipsticks – available in Lip Kits with accompanying lip liners. “The lipstick tip is angled to mimic the precision of a lip brush, so you can apply it straight from the bullet,” she says. We also love Tom Ford, Dior and MAC for traditional bullet formulas, though if you are working with a lipstick that doesn’t offer ideal precision, a lip brush (such as the Chanel Duel Ended Lip Brush) can help.

Anyone struggling to choose the right shade of lipstick should try a lipstick shade finder, such as the Charlotte Tilbury one (yes… she’s thought of everything). “Easy and accurate, the algorithm uses my expert artistry to match you with your most flattering shaded,” she explains.

But the renowned make-up artist Peter Philips, the creative and image director for Dior Makeup, has some advice for us too, here: if you’re new to bold colours – or to lipstick in general – "start with a less visible shade," he advises. "I always say it's like wearing heels: don't go straight to a stiletto. Start with a medium heel, something more comfortable to get used to the walk, to the sensation, to the whole thing." Once you are used to wearing lipstick in general, it's easier to embrace bolder shades, he says.

4) Ensure its longevity

To ensure longevity of your lipstick and prevent transfer (onto your teeth and others…), Tilbury has two key tips. “A great trick, especially after applying red lipstick, is to take a tissue, place it over the lips, and lightly dust with a finishing powder to lock the colour in. Finish with a second coat of lipstick.”

Or, if you’re applying a full make-up look, spritz some setting spray “over the entire face”, she suggests. It will set your lipstick in place and mean “no melting, no fading and no creasing”.

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Ezra Shaw - Getty Images

As for the most frequent lipstick mistake – transfer onto the teeth – Philips notes that this to do with where you place your lipstick. He explains: "The best way to avoid this is, after application, to suck your finger and pull it out of your mouth – because what goes onto your teeth is actually from what's on the inside of your lip." If you do this, everything that is on the inside of your lip will be on your finger and you can just wash it off your hands. "That’s a classic trick that’s as old as lipstick!"

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