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Popular ‘It Girls’ in Their 50s and Beyond: See Your Favorites, Then and Now

Samantha Franco
Photo Credit: Paramount Pictures / Sunset Boulevard / Corbis / Getty Images and Ron Galella / Ron Galella Collection / Getty Images

In their prime, these “It Girls” were the idols of young women everywhere. Even today, they continue to stun fans and wow the public with their iconic style, class, and beauty. Now, the “It Girls” of the past are more than a half-century old, and they look just as radiant as ever.

Winona Ryder

Winona Ryder in 1989 and 2022

Left: Winona Ryder attending the Athletes Entertainers Kids Benefit, circa 1989. (Photo Credit: Jim Smeal / Ron Galella Collection / Getty Images) Right: Attending “Stranger Things” season 4 premiere at Netflix Brooklyn in New York City on May 14, 2022. (Photo Credit: ANGELA WEISS / AFP / Getty Images)

Winona Ryder became one of the most recognizable actresses of the late 1980s and ’90s, starring in films like Beetlejuice (1988), Edward Scissorhands (1990), and Girl, Interrupted (1999).

Ryder kept busy throughout the decades through acting and producing. Now, at 50 years old, she is best known for her role on the hit Netflix series, Stranger Things

Halle Berry

Halle Berry, then and now

Left: Actress Halle Berry stands at the Essence Awards April 26, 1996 in New York City. The ceremony honors African-Americans who represent positive role models to the community. (Photo Credit: Evan Agostini / Liaison) Right: Halle Berry Poses at the 27th Annual Critics Choice Awards at Fairmont Century Plaza on March 13, 2022 in Los Angeles, California. (Photo Credit: Steve Granitz / Getty Images)

Halle Berry was a feminine icon thanks to her roles in Catwoman (2004) and Introducing Dorothy Dandridge (1999). She even played a Bond girl in Die Another Day (2002). Berry made history when she became the first African American female to win the Oscar for Best Actress for her performance in Monster’s Ball in 2002.

At 56 years old, Berry prefers grittier roles and has starred in recent films such as Kidnap (2017), John Wick Chapter 3: Parabellum (2019), and Bruised (2020).

Lauren Hutton

Lauren Hutton then and now

Left: Lauren Hutton (Photo by Ron Galella/Ron Galella Collection via Getty Images) Right: Hutton at The Fashion Awards 2019 held at Royal Albert Hall on December 02, 2019 in London, England. (Photo by Lia Toby/BFC/Getty Images)

During the 1970s, Lauren Hutton became one of the most iconic models in America, known for the signature gap between her teeth. Before her big modeling break with Revlon, Hutton also pursued a career in acting, and can be seen in films such as Paper Lions (1968), The Gambler (1974), and American Gigolo (1980).

Hutton continues to model, and at 78 years old, looks just as good doing so today. She’s the face of iconic companies like H&M, Alexander Wang, Tom Ford, and Bottega Veneta.

Cindy Crawford

Cindy Crawford in 1990 and 2021

Left: Cindy Crawford promoting her fragrance “Halston” at Bloomingdale’s in New York City, February 26, 1990. (Photo Credit: Ron Galella / Ron Galella Collection / Getty Images) Right: Model Cindy Crawford arrives at Omega San Francisco Grand Opening VIP Celebration at de Young Museum on November 18, 2021 in San Francisco, California. (Photo Credit: Miikka Skaffari / Getty Images)

Cindy Crawford was arguably the supermodel of the 1980s and ’90s. Stretching into other areas in the public eye, Crawford tried her hand at acting in Fair Game (1995) and also became a television personality.

Crawford has become extremely successful over the years. At 56, she continues to model, runs her own company called “Meaningful Beauty,” and acts as a spokesperson for Omega watches.

Bianca Jagger

Bianca Jagger with a bird at Studio 54 and today

Left: Model Bianca Jagger holds doves while at a party thrown by fashion designer Halston at Studio 54. (Photo Credit: Bettmann / Contributor) Right: Bianca Jagger attends WomenNOW Summit by Santander Bank at the Reina Sofia Museum on March 29, 2019 in Madrid, Spain. (Photo by Carlos R. Alvarez/WireImage)

Former model and actress Bianca Jagger appeared on shows like Miami Vice and Hotel, and in the film The Cannonball Run (1981). Her marriage to Mick Jagger skyrocketed her to fame, and she became a staple of Studio 54.

Now 77 years old, Jagger has become a fervent human rights advocate and has created her own charitable organization. For decades she has been working with various organizations and sits as a goodwill ambassador on the Council of Europe.

Courtney Love

Courtney Love, then and now

Left: Courtney Love in a white shoulder-less dress, circa 1995. (Photo Credit: Mitchell Gerber / Corbis / VCG / Getty Images) Right: Courtney Love attends Fat Tony’s clean-time birthday at Il Borro Tuscan Bistro on January 10, 2022 in London, England. (Photo Credit: David M. Benett / Dave Benett / Getty Images)

Courtney Love was one of the frontrunners of the grunge era of the 1990s. As the lead singer for Hole, her music paved the way for future artists and her rocker fashion sense brought about a whole new era of alternative couture.

Now, at 58, Love has been pursuing some of her other talents, including writing and designing her own clothing label. However, Love is still actively writing music.

Demi Moore

Demi Moore then and now

Left: Demi Moore with short hair and wearing a spaghetti strap top, circa 1990. (Photo Credit: Paramount Pictures / Getty Images) Right: Demi Moore attends the Chloe Womenswear Fall/Winter 2022/2023 show as part of Paris Fashion Week on March 3, 2022 in Paris, France. (Photo Credit: Pascal Le Segretain / Getty Images)

Demi Moore became best known for her acting credits in Ghost (1990), A Few Good Men (1992), and G.I. Jane (1997). She was a natural beauty whose name we are still confused about how to pronounce.

These days, Moore continues to act. She’s also explored other talents and at 59 years old has come out with a memoir about her life and career.


Twiggy then and now

Left: London, England: Close-up of the English model Twiggy. (Photo Credit: Bettmann / Contributor) Right: Twiggy during the Platinum Jubilee Pageant on June 05, 2022 in London, England. (Photo by Samir Hussein/WireImage)

In the 1960s, Twiggy revolutionized the model look. Her thin build, short hair, and large eyes became the most recognizable faec of the UK’s swinging ’60s style. Her look quickly spread globally, and she became an international modeling icon. Her success gave her the opportunity to try singing and acting, and she can be seen in the film The Boy Friend (1971) which earned her two Golden Globe Awards.

Now, at 72, Twiggy has accomplished many things in her life, including being dubbed Dame Lesley Lawson (though she prefers Dame Twiggy) by the British Empire. She also hosts her own podcast called Tea with Twiggy. 

Meg Ryan

Meg Ryan in 1988 and 2021

Left: Meg Ryan at the “Promise Land” premiere, circa 1988. (Photo Credit: Ron Galella / Ron Galella Collection / Getty Images) Right: US actress Meg Ryan arrives for the 11th annual amfAR Gala Los Angeles at the Pacific Design Center in West Hollywood, California, November 4, 2021. (Photo Credit: ROBYN BECK / AFP / Getty Images)

Meg Ryan got her debut acting gig in Rich and Famous in 1981, and went on to become a romantic comedy legend. She starred in rom-com staple films like When Harry Met Sally… (1989), Sleepless in Seattle (1993), and You’ve Got Mail (1998).

Ryan is now 60 years old and took a break from acting for a while, but has decided to take up her love for rom-coms once again, as she plans to star in future films.


Iman in the 1970s and today

Left: Model Iman launches her modeling career. (Photo Credit: Bettmann / Contributor) Right: Iman attends The 2021 Met Gala Celebrating In America: A Lexicon Of Fashion at The Metropolitan Museum of Art on September 13, 2021 in New York City. (Photo by Gilbert Carrasquillo/GC Images)

The beautiful Iman became the modeling muse of major fashion designers like Gianni Versace, Thierry Mugler, Calvin Klein, and Yves Saint Laurent. Her long neck, slender figure, and smooth skin put her on the front of some of the world’s most famous magazines in the late 1970s. She married music icon David Bowie, and even started her own cosmetics line in the 1990s.

At 67, Iman has taken a step back from modeling but still stays active in the fashion world. She can also be seen sporting beautiful looks on various runways, still turning heads with her stunning good looks.

Michelle Pfeiffer

Michelle Pfeiffer then and now

Left: Actress Michelle Pfeiffer attends the “Grease 2” Premiere Party on June 9, 1982 at the Red Parrot in New York City. (Photo Credit: Ron Galella / Ron Galella Collection / Getty Images) Right: US actress Michelle Pfeiffer attends Showtime’s FYC event and premiere for “The First Lady” at the DGA Theater Complex in Los Angeles, April 14, 2022. (Photo Credit: ROBYN BECK / AFP / Getty Images)

Michelle Pfeiffer was an absolute blonde bombshell of the 1980s and 1990s. She starred in iconic films such as Scarface (1983), Married to the Mob (1988), and even starred as Catwoman in Batman Returns (1992).

Pfeiffer’s acting career has slowed in recent years, though she does still appear on the Showtime Series The First Lady. At 64 years old, Pfeiffer has instead turned her focus on her family.

Jane Birkin

Jane Birkin then and now

Left: English actress and singer Jane Birkin, circa 1970. (Photo by Keystone/Hulton Archive/Getty Images) Right: Jane Birkin performs during Immortel Show in memory of Alain Bashung at Le Grand Rex on October 2, 2019 in Paris, France. (Photo by David Wolff – Patrick/Redferns)

When Jane Birkin came onto the scene in the 1970s, she quickly became a fashion icon. Her haute-hippie style accentuated her beauty and sex appeal, and she became an internationally known actress and singer. She gave inspiration to the incredibly popular designer Birkin bag by Hermès.

At 75, Birkin is still stunning. She often visits with her children and has produced multiple memoirs about her life. Her latest studio album, Oh! Pardon tu dormais…, was released in December 2020.

Cyndi Lauper

Cyndi Lauper then and now

Left: Cyndi Lauper at the Lhasa in Los Angeles, California on January 9, 1984. (Photo Credit: Barry King / WireImage / Getty Images) Right: Cyndi Lauper attends MusiCares Person of the Year honoring Joni Mitchell at the MGM Grand Marquee Ballroom on April 1, 2022 in Las Vegas, Nevada. (Photo Credit: Jeff Kravitz / FilmMagic / Getty Images)

Cyndi Lauper took over the music world during the 1980s. “True Colors” and “Girls Just Want To Have Fun” continue to be popular songs that everyone knows the lyrics to without realizing it. Her crazy style and hair also came to be a symbol of the decade. Unchanged: Cyndi Lauper took over the music world during the 1980s. “True Colors” and “Girls Just Want To Have Fun” continue to be popular songs that everyone knows the lyrics to without realizing it. Her crazy style and hair also came to be a symbol of the decade.

At 69 years old, Cyndi is still turning heads with her incredible style, going on tour for her music, and has also become an author, recently publishing her autobiography. Unchanged: At 69 years old, Cyndi is still turning heads with her incredible style, going on tour for her music, and has also become an author, recently publishing her autobiography.

Jennifer Aniston

Jennifer Aniston then and now

Left: American actress Jennifer Aniston of the television comedy, Friend’s, attends the 1995 NBC Fall Preview circa 1995 at the Lincoln Center in New York, New York. (Photo Credit: Ron Davis / Getty Images) Right: Jennifer Aniston arrives at the 26th Annual Screen Actors Guild Awards at The Shrine Auditorium on January 19, 2020 in Los Angeles, California. (Photo Credit: Steve Granitz / WireImage / Getty Images)

Although her acting career began well before her role on the sitcom Friends, Jennifer Aniston became best known for her role as Rachel on the television series that ran for 10 seasons.

More from us: Jerry Seinfeld Told Lisa Kudrow His Show Helped with Friends’ Success

At 53, Aniston continues to act and has taken a liking to comedy films including Horrible Bosses (2011) and We Are The Millers (2013). She has also become the face of beauty brands like Aveeno and Living Proof.

Samantha Franco

Samantha Franco is a Freelance Content Writer who received her Bachelor of Arts degree in history from the University of Guelph, and her Master of Arts degree in history from the University of Western Ontario. Her research focused on Victorian, medical, and epidemiological history with a focus on childhood diseases. Stepping away from her academic career, Samantha previously worked as a Heritage Researcher and now writes content for multiple sites covering an array of historical topics.

In her spare time, Samantha enjoys reading, knitting, and hanging out with her dog, Chowder!