When your autumnal plum lipstick isn't quite dark enough, follow in Rihanna's lead and use your eye makeup kit as a resource. To create the saturated blackberry hue the star wore at the MTV Video Music Awards this year, her makeup artist Mylah Morales did just that, and used a layer of Chanel's Le Krayon Khol in Noir ($30; nordstrom.com) under a swipe of the Rouge Allure Velvet in Rouge Audace ($37; nordstrom.com) to help deepen the color. "I used the liner all over the lips first, then applied the color directly on top to add dimension," she explains. "I was really inspired by old Hollywood glamour, but particularly the black and white pictures and the silent films—the lip is dark, but you don't really know what the color is."
A shade like this one can work against any skin tone, but make sure to stick to neutrals elsewhere on the face so that the lip remains the focal point. Morales advises using brown shades on your eyes, and then giving your complexion a little warmth with a swipe of bronzer or blush.
Since deeper tones have the tendency to make small lips look even smaller, try lining your pout slightly outside of its natural shape to create a larger appearance—but put a strong emphasis on the word slight. "You don't want to veer too far outside of your natural lip line, but just enough to make the shape a bit fuller," Morales says. "Don't overdo it. That's the key." To finish, pick up some translucent powder on a small brush, then apply a thin layer just outside of your lip line to prevent the color from moving or bleeding.
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