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11 Iconic Red Lipstick Looks, Explained

Wearing red lipstick has always meant more than just a logical color match for your wardrobe. Choosing red often intimates a chic, confident, and sexy vibe. For years science has well documented the fact that seeing the color red sends signals to the brain ideas of sexual attractiveness. Red lipstick connotes power and has the ability to uplift your mood and make you feel alive. In honor of the power red lipstick has to inspire, we’re celebrating with the stories behind some of the most iconic red lipstick moments in pop culture history—as told by the makeup artists who created them.

MAC’s Russian Red, as worn by Madonna during her “Blond Ambition” tour in 1990.

“I do remember it was early 1990 that Madonna and I visited MAC’s Frank & Frank’s store in Canada to choose colors for her,” says Joanne Gair, Madonna’s makeup artist for the artist’s “Blond Ambition” tour, says. She was the lead artist who created the bespoke MAC shade for the pop icon’s run of unforgettable shows in 1990. “There were discussions with one of the Franks that day about a lipstick for her. Madonna chose the highly pigmented Russian Red as her signature color lipstick for the “Blond Ambition” tour that was to start on April 13th in 1990. This was also to be my first concert tour ever. Before meeting with MAC, Madonna knew exactly what she was looking for. As a well-versed performer she had great knowledge of what stage makeup would read if, by chance, the monitors on either side of the stage went down. A great deal of discussion went into her look between all of us that day, and what would be the most successful products for her to consider. Considering all the obstacles—like her performing on stage nonstop for two-plus hours with multiple quick costume changes—it was vital that the makeup would hold up. My job was to absorb and interpret all that was requested and bring the look together—including maintaining that ponytail that Peter Savic had designed for this tour.

Photo Credit: Frank Micelotta / Getty Images

Madonna performing on the Blond Ambition Tour in Tokyo on April 4, 1990.

“Madonna was very clear on what she needed from all of us. She wanted her features not to disappear (this included even eyebrows) so her face had expression, even for those fans way at the back, if the monitors were not working. Her eyebrows were very important, and therefore looked stronger than normal. She wanted her eyebrow to have an arch, she wanted her lipstick to hold up against having a head set microphone on and off throughout all the changes. We used MAC Lip Liner in Cherry before Madonna went out on stage because it registers a little darker than the Russian Red lipstick, and gave gradated shape to the mouth. Her gorgeous porcelain skin was, indeed, like velvet to work with, but it was the MAC face powder that they custom-made for Madonna that was, for me, really what brought this look to perfection.

“She would be drenched from her highly active dance performances each time she came under the stage for a costume change and touchups. While clothes were being taken off her and another costume put on, I cooled her down with chilled water and mopped her face constantly with Viva paper towels. Then, at the last minute—as so much movement was happening—I would hand her the Russian Red on still perfectly defined lips. If needed, I would touch up the eyebrows which may have been bumped with the costume change—and finally, before she rose to the stage again, I would apply the glorious MAC powder. I still have a little of this powder left—and have only ever used it on her as it’s made for her alabaster skin. I’m looking at the small container in front of me right now; it has a gentle, light pink hue.

Photo Credit: Rob Verhorst / Redferns

Madonna performs on stage at Feyenoord Stadium, Kuip, Rotterdam, Netherlands on the Blond Ambition World Tour, 24th July 1990.

“This was her signature look for the the “Blond Ambition” tour. At the end of a night’s performance, we all had to do a mad exit after packing up (as the stage would usually be moving to the next location that night), and race to whichever vehicle or bus that was allotted that evening, depending on which country we were in. Fans would somehow make a race to, of course, get to Madonna, the dancers, and even any of us. So Madonna would take her makeup off herself on performance nights in her hotel suite.”

Grace Kelly’s favorite: Rouge Dior Lipstick by Dior

Just like her fellow screen and stage legends Marlene Dietrich, Josephine Baker, and Edith Piaf, Grace Kelly, one of Hollywood’s most glamorous and successful actresses, was a loyal devotee of Rouge Dior Lipstick. She wore the shade from its launch in the mid-1950s onward. There was even an exhibition dedicated to Princess Grace at the Dior Granville Museum in 2019, in which some of Kelly’s most treasured pieces were on display: among them, a box of 14 Dior lipsticks gifted to her by the House of Dior.

Photo Credit: Herbert Dorfman/Corbis via Getty Images

Valentina Sampaio at the 2021 Met Gala

“I loved using Giorgio Armani Beauty Lip Power Lipstick in 200 for Valentina Sampaio for the Met Gala—Valentina’s first ever,” the celebrity makeup artist Molly R. Stern says. “I wanted her to feel effortlessly glamorous and this rich, warm, red was the perfect choice for the night. Red lips are an easy and reliable way to give my clients the boost of confidence and enchantment for any red carpet.”

Photo Credit: Arturo Holmes/MG21/Getty Images

Valentina Sampaio attends The 2021 Met Gala Celebrating In America: A Lexicon Of

Fashion at Metropolitan Museum of Art on September 13, 2021 in New York City.

Red (Taylor’s Version)

Very rarely is Taylor Swift without her signature red lip look. The pop star often relies on Nars’ Dragon Girl lip pencil to achieve the trademark glam look. It’s one of the most timeless shades—which she wears with effortless sophistication.

Photo Credit: Gotham / GC Images

Taylor Swift attending Gigi Hadid's Birthday Party on April 22, 2019 in New York City.

Janelle Monae at the 2020 Oscars

“Janelle’s Ralph Lauren dress was the focus with this look,” explains celebrity makeup artist Jessica Smalls. “It was created with hundreds of crystals—and instead of trying to compete with the dress, I decided to have the makeup look be the costar, sticking with the tried-and-true classic look with a bit of sparkle. It was, nonetheless, still a timeless and iconic look that can we worn any time of year, in any period.

Photo Credit: Kurt Krieger / Corbis via Getty Images

Janelle Monae arrives at the 92nd Annual Academy Awards at Hollywood and Highland on February 9, 2020 in Hollywood.

“I always collaborate with the hair and wardrobe stylist because that’s how you create a look that flows magically. The lip was Nars Dragon Girl. After I applied the lipstick, I had her blot her lips with tissue and dusted a translucent powder over her lips while the tissue was still holding; this helps lock the color in. The foundation was Koh Gen Do Maifanshi Moisture Foundations in #302 and #303. I used MAC Texture and Embark on her eyelids and lined her eyes with black liquid liner and applied Urban Decay glitter liner in Glam rock.”

Continue exploring all the gorgeous red-lip looks via W Magazine.



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