11 Iconic Red Lipstick Looks, Explained

“The rules for wearing red lipstick are that there are no rules, just like in Fight Club,” Debbie Harry tells me over e-mail when I ask her to describe the ethos behind her standout makeup looks. Who am I to argue with the Blondie legend when it comes to red lipstick decorum? Her iconic on-and-off stage beauty looks, after all, were constant, indelible perfection—in part due to the fact that she never shied away from a bold red lip (accompanied, of course, by layers of sexy blonde locks swooped over one eye and a fierce jolt of confidence).

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. Elizabeth Taylor famously counseled women to “pour yourself a drink, put on some lipstick, and pull yourself together.” (Incidentally, she was a die-hard fan for years of Elizabeth Arden’s Rouge lipstick and, years later, MAC’s Ruby Woo.) In honor of the power red lipstick has to inspire, we’re celebrating this Valentine’s Day 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.

“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.

“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.

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.”

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.

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.

“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.”

Marilyn Monroe

Almost six decades later, and no one has managed to outdo the sex appeal of Marilyn Monroe’s sultry, trademark red lips. Her look was pulled off using five coats of Guerlain’s #25 Satin from the Rouge G collection—worn to premieres, on movie sets, and for the majority of Monroe’s public appearances.

Angelina Jolie at the 2012 Academy Awards

“The two classic reds we always had in Angelina Jolie’s makeup bag were Russian Red and Ruby Woo from MAC,” Jolie’s makeup artist, Tony G, says. “We’d try other reds as well, but for a long period, it’s been Russian and Ruby. For the unforgettable black velvet dress look during the 2012 Oscars, we went with Russian Red.

“It was over a decade ago, but I fondly remember the look we created. If I remember correctly, she was going to wear either a black velvet Versace dress or another shimmering, gold dress. Both were beautiful and I was hoping for the gold, but then she tried the black one and it was very hard to choose. In the end, she thought the gold was too much. She laughs about it now because the black velvet dress with the slit was supposed to be the toned-down, cozy dress—but ended up being a far more memorable dress. She was so comfortable in that dress, maybe that’s why she was feeling and looking so sexy.

“We did, at one point, consider a nude lip with the black velvet dress, but MAC’s Russian Red looked perfect with both dresses. She’s a pro at doing her lips, so often, she does the lipstick herself. I always make sure to give her a lipstick to have at the event. I honestly can’t remember if we used a pencil or not, but if we did use a pencil, it would have been from MAC.”

Margot Robbie at the 2020 Oscars

“For the 2020 Oscars, Margot Robbie wore a deep navy Chanel gown,” recalls Pati Dubroff, who created Robbie’s makeup look at the Academy Awards. “To complement this, we decided that a very velvety matte red lipstick was the way to go, and I used Chanel’s Rouge Allure Velvet Extrême in Idéal. I choose this true red shade as it was a perfect balance of a bright red, but still had depth and richness. It’s a very intense and matte formula which helps with long wear and staying powerful. A couple coats of this lipstick will have a great hold and not require constant touchups.

“The gown was originally a couture piece from the ‘90s so we definitely channeled cool ‘90s supermodel vibe into the look. Also, the pop of red and the sleek hair added an old Hollywood feeling, but it was deconstructed just enough to keep the look modern—more in line with this idea of a ‘90s supermodel. The depth of the blue from the dress really allowed the red to pop.”

Debbie Harry, in Her Own Words

“At first, when I was a young adult, I liked very much to experiment with makeup and, depending on the trends of the day, would vary my look as much as possible,” Harry says. “Sometimes to great success—other times to great disaster. (Live and learn.) Red lipstick can be one of the disasters with smearing and bleeding, but then again, these can be intriguing looks to develop. I didn’t always wear red lips and the shades of red varied according to what I was wearing, my mood, or whatever I had available. I always like shades that had names that implied something wild, tempting, or nasty.

“As with music, my influences are wide—which I think helped me establish the things that looked best on me. Of course, the amount of time I had to apply made a huge difference and what the makeup was for, i.e. photography or stage. I never had the time to go off stage and reapply lips. If I did reapply, I’d make it part of the show.”

Jennifer Lopez at the 2011 Met Gala

Once again, Jennifer Lopez dressed to impress at the 20011 Met Gala in a bold, ultra-feminine red Gucci dress. To highlight the dress as the main attraction, she had hair slicked back in an updo, showcasing her flawless makeup: including a pop of color on the lips, using L’Oréal Paris Infallible Le Rouge in Bold Bordeaux.

Rachel Brosnahan at the 2018 Emmy Awards

“The Oscar de la Renta dress and the jewelry were everything for Rachel’s Emmys look,” Brosnahan’s makeup artist, Lisa Aharon, says. “We were definitely drawing all the inspiration from the diamonds and gorgeous red hues of her gown. It was a very elegant look overall, but we did want to keep the makeup fresh—a heavy eye just didn’t feel right for this one. Alas, we landed on a bright, bold red lip to complement her glowing skin and flirty lashes. It leaned old Hollywood, but in a very modern way.

“I used all Chantecaille products for this look. For the lips, I applied Lip Keep for longevity under Lip Veil in the strong, flattering, coral shade Tiger Lily, complimented by Lip Definer in true red Desire.”