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6 Ways To Wear a Red Lipstick

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The Violet Files

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Makeup artist Rachel Goodwin celebrates the high-impact red lip through the decades and updates the look in a collection of tutorials created exclusively for The Violet Files.

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A few beauty facts that might come in handy during your next cocktail conversation: The wealthiest (and most well-prepared) women of ancient Egypt were buried with pots of their signature lip paint—essential for beauty routines in the afterlife. Max Factor himself drew the shapely Cupid’s bows on twenties silent screen stars not to define their expressive pouts and set a new beauty standard, but rather to keep the pigmented greasepaint from bleeding out into their pancake makeup. Madame de Pompadour, King Louis XV’s mistress, determined social ranking for ladies of the French court (birthplace of the term silently judging) by the richness of their lip color. These are just a few salient tidbits I picked up from makeup artist Rachel Goodwin, whose penchant for beauty history makes breakfasts over lattes and on-set breaks for The Violet Files shoots so much more enjoyable.

Earlier this summer, over a plate of Cecconi’s lobster spaghetti, the immensely talented red-haired artist (clients include Emma Stone, January Jones, and Amber Valletta) sent me into an absolute beauty tizzy with her wealth of red-lip trivia. “Coco Chanel was the first to really popularize red lipstick, and she wore it for herself—not for you, not for her man,” says Goodwin, who is also a celebrity makeup artist for the venerable house. “Chanel’s original 2.55 bag originally included a special compartment designed specifically to hold a bullet of red lipstick. This is how quintessential Coco thought red lipstick was to a woman.”

Somewhere between gushing over Winona Ryder’s imperfectly perfect matte red lips of the nineties and the mesmerizing shade of Queen Nefertiti’s crimson mouth (“Did you know they crushed beetle wings for that shine?”), we solidified plans for a photo shoot that would celebrate the power of the ever-iconic red lip. While at times controversial (beloved for its beauty, scrutinized for its sensuality), the seemingly simple red lip has managed to make its mark throughout history. “It comes down to this: Red lipstick is bigger than the color. It has a voice,” Goodwin notes. “One that says, ‘You’re confident, you’re sexy’ in one little tube.” Here, Goodwin enlists iconic supermodel Amber Valletta to show off her one-of-a-kind takes on signature red lips from six different decades.

Amber Valletta


MUSE: “Red is a color of passion, power, and femininity. Its legacy has lasted throughout history, starting with Nefertiti’s bright red lips. You won’t see a statue of her without them.”

GET THE LOOK: “To mimic Nefertiti’s regal nature, I elongated and modernized the shape of the cat eye and then outlined the bottom line with Chanel’s waterproof pencil in Marine, amplifying the shade with the greenest shadow in Chanel’s Tissé Vénitien eye shadow quad. I gave the embellished lips an iridescent, metallic effect by tapping a shimmering pigment over the lipstick. In ancient times the same look was achieved by crushing beetle wings into a fine powder.”

Amber Valletta
Amber Valletta
Amber Valetta


MUSE: “The sensual flushed cheek and stained lip look, popularized by women of the eighteenth century, is as effective now as it was in King Louis XV’s royal French court.”

GET THE LOOK: “Heavy face powder, which was responsible for the fashionable pale complexions of the day, blurred the outer rims of the mouth, thus creating a diffused, stained lip effect. To achieve a similar look, apply red lipstick with your fingers to the center of the mouth, press lips together, and blot away excess pigment with a tissue. Dab the same lipstick onto cheeks for that just-pinched healthy glow.”

Amber Valletta


MUSE: “Silent film actress Theda Bara was the femme fatale who reigned supreme during the twenties. She eschewed traditional feminine roles and embraced characters that were confrontational and unafraid. She was the original ‘vamp’ during a time when women were exploring their masculine energy and feeling rebellious.”

GET THE LOOK: “The twenties lip is synonymous with a deep, dark burgundy, but the silent screen stars were actually wearing a true vermillion—the sepia tone of the film cast a more vampy shade. A modern take requires a slightly glossy lip paired with a reflective, monotone eye and almost no mascara. The effect is impossibly alluring.” Click here for the complete tutorial.

Amber Valletta


MUSE: “Red was such a signature color of the fifties—it was beguiling. Model Dorian Leigh made the look famous in Revlon’s iconic ‘Fire & Ice’ campaign, photographed by Richard Avedon. There was an air of sophistication that came with the arrival of the matching-lip-and-nail look (a first at the time). Pan Am flight attendants were even required to wear the lip color to work.”

GET THE LOOK: “I fantasize about an era when it was normal to take two hours to get dressed for any occasion, even if it was just making popcorn. I paired Amber’s red lip with liquid liner and a wash of mint green shadow on the eyes as a nod to fifties glamour. I think the matchy-matchy concept still exists today: The most elegant, chic beauty look consists of a woman wearing red lips and nails with a cotton T-shirt and jeans or a black suit.”

Amber Valletta


MUSE: “Winona. Drew. A brick.”

GET THE LOOK: “This is the girl who cares, but not too much. She’s the sexy rebel. It’s not an exact science, but she clearly slept in her makeup last night, and this morning she touched up her lipstick just a bit. She looks like she didn’t try, but she definitely did. Take Chanel’s Noir Intense liner and smudge it over and under your lash lines with a fingertip. A dab of RMS Living Luminizer in the corner of your eyes brings a lived-in lightness to the look.” 

amber valletta


MUSE: “After centuries of the red lip symbolizing scandal, femininity, or downright defiance, we have finally entered an era where wearing red is our right. My muse for this decade is Amber. I began working with her in 2003 and have always wanted to do a shoot like this with her. Red isn’t passive, and neither is she.”

GET THE LOOK: “The texture has to be perfect: It’s both creamy and matte, and not too shiny. Wear it with messy hair, almost no other makeup, and a leather jacket, and you will feel like you can take over the world.”