beauty

The Best Red Lipstick Moments in History

Allure

By Meirav Devash. Photos: Getty Images, Courtesy of Instagram, YouTube.

“Heels and red lipstick will put the fear of God into people,” Dita Von Teese once told the New York Times, and she ought to know. Red lipstick has been a staple of femininity since Cleopatra wore a paste made from crushed carmine beetles and ants, but it has been a wild ride. We rounded up the best moments in red lipstick history and the It Girls who made them happen.

This story originally appeared on Allure.

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Queen Elizabeth I Reigns in Rouge

To rule over 16th century England, Elizabeth—also known as the Virgin Queen—didn’t need a man, but she did require a swipe of bold, red lip rouge to set off her regal pallor. Unfortunately, the red lipstick of the time was made with toxic mercuric sulphide, and her foundation, called Venetian ceruse, was made with dangerous lead and vinegar. She eventually died of blood poisoning, rumored to have been caused by her noxious cosmetics.

Elizabeth Arden Votes Yes

It seems ridiculous to us that you could be an entrepreneur and girlboss who still didn’t have the right to vote, but that was the world at the turn of the 20th century. For beauty industry maven Elizabeth Arden, red lips really started to signify empowerment at the 1912 New York City Suffragette March—she and 15,000 other women protested for equal rights while wearing red lipstick courtesy of the cosmetics brand.

Frida Kahlo Masters the Selfie

In the 1930s-40s, Frida Kahlo was one of Mexico’s most well-known painters, a feminist, a political activist, and a devoted red lipstick wearer. Her signature look has been captured in the dozens of self-portraits she left behind—center-parted braids woven with flowers and ribbons, a dusky mustache and unibrow, and bright, bold lips—and she was known to sign her letters with lipstick kisses. (Salma Hayek portrayed her onscreen in Frida, 2002.)

Rita Hayworth is the Original Lady in Red

With her red hair set in Old Hollywood waves, creamy red lips and red nails to match, Rita Hayworth was basically an ambassador for the shade. The bombshell was also a frequent Max Factor model throughout the 1940s in ads for Tru-Color, the first smear-proof lipstick.

Everyone Gets Matchy-Matchy

Rita was so ahead of the game, right? By the time the ads for Revlon’s Fire and Ice Collection “for lips and matching fingertips” came out in 1952, women were more than ready. The ad, shot by Richard Avedon and starring supermodel Dorian Leigh, was a huge hit and so was the makeup/ nail polish duo. (It’s still studied in business schools as one of the most successful campaigns ever.) Fire and Ice made headlines again in 2010 when the set was re-released with a reshoot of the iconic ad by Mario Testino, starring Jessica Biel.

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Gentlemen Prefer Marilyn

Though red lips had already been worn by every Hollywood actress, magazine pin-up, and school nurse by 1953, this red lipstick moment from Gentlemen Prefer Blondes is the unforgettable one for generations of makeup artists: Marilyn Monroe, singing “Diamonds Are a Girl's Best Friend” in a strapless pink dress and gloves. (The scene was recreated in 1985 for Madonna’s “Material Girl”

Blondie Punks it Up

Red lipstick lost its luster with ’60s mods and ’70s hippies, who preferred their lips neutral or pastel-colored. It took a hit of rebelliousness to shake off red’s too-polished reputation: Debbie Harry wore it with sooty eyes, super-sharp contoured cheeks, and a pissed-off expression.

MTV Gets Addicted

Robert Palmer’s "Addicted to Love" music video premiered in 1986, and was basically never not on MTV after that. The iconic video featured Palmer performing with fake band members, models done up in the distinctive contemporary deco style of artist Patrick Nagel: Mannequin-like pale skin, smoky eyes, contoured blush, and most importantly, glossy, blood-red lips.

Madonna Takes Russian Red on Tour

When Madonna was gearing up for her 1990 Blonde Ambition tour, she needed a lipstick to match her vampy stage show. A little up-and-coming cosmetics company called M.A.C. (you may have heard of them) created Russian Red for her tour—a super-sexy matte crimson with cool undertones. It’s been a cult classic ever since.

Carolyn Bessette-Kennedy, Reluctant Street Style Star

There was no greater “catch” in the 1990s than John F. Kennedy Jr., so it was no surprise that the stylish woman who married New York’s most famous bachelor would become a national obsession. The former PR rep for Calvin Klein avoided the spotlight—she never gave a single interview—but that didn’t stop the paparazzi from taking photos in Tribeca of her chic, minimalistic outfits and seemingly effortless red lipstick, until the couple’s tragic plane crash in 1999.

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Marilyn II: Reality TV Red

Like a phoenix rising from a dumpster fire, Anna Nicole Smith was the Marilyn Monroe for a new, trashier millennium—all blonde hair and curves, wide eyes, and a bright red pout. The former stripper and popular Playboy model gained legit fame as a Guess model, but is more known for a gold-digging marriage to 89-year-old oilman J. Howard Marshall II, wild weight fluctuations, and crazy antics on E!’s The Anna Nicole Show. (Like her idol Marilyn, she died of a lethal overdose of prescription pills.)

A Little Bit Fashion, A Little Bit Rock 'N Roll

Just when the MTV generation had reached peak bleached-blonde-with-giant-breast implants, Gwen Stefani pouted her way into the spotlight with a tube of red lipstick, an unapologetically athletic build, and a killer sense of style. Through all her incarnations—alt-girl No Doubt front-woman, hyper-stylized solo artist, L.A.M.B. designer, mom of boys—one thing remained constant: The red lipstick. (We regret to report that since her divorce from Gavin Rossdale, The Voice judge’s signature lipstick has made itself scarce. People theorized{: rel=nofollow} her new man Blake Shelton’s fear of smooch-related smears may be at blame.)

Good Girls Wear Red, Too

Bless her heart, leave it to America’s sweetheart Taylor Swift to make red lipstick her signature shade. She told People{: rel=nofollow} (humbly, of course) she wore it because her face “looks worse without it," she has sung about her lipstick, and made headlines in 2015 when she switched her go-to shade from Nars Dragon Girl to M.A.C. Lipstick In Ruby Woo. (“It’s a staple. I was the last person to discover it,” she said{: rel=nofollow}.)

Rihanna is a Woo Girl

You know who didn’t wait until 2015 to discover M.A.C. Ruby Woo? Rihanna. In fact, Riri was such a huge fan of the shade, she made her own limited-edition version called Riri Woo with M.A.C. two years before Taylor knew the original existed. The Rihanna version was a touch more pink than its sister shade, and sold out in three hours.

Boy, Oh Boy

When YouTube star James Charles’s senior high school photos went viral (he brought a ring light “so my highlight would be poppin”), the 17-year-old probably didn’t realize it would lead to becoming the first male CoverGirl spokesmodel. Easy, breezy proof positive that literally anyone can—and should—pull off red lipstick, beautifully.

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