Ahh, the ’90s. A time of “Sassy” and “Jane” magazines, MTV playing actual music videos, and devastatingly overtweezed eyebrows. We’ve brought back many of the decade’s biggest trends, from Doc Martens and babydoll dresses to chokers and Lisa Frank – we’ve even rebooted some of the classic shows, like “Boy Meets World,” “Full House,” and “The X-Files.”
In addition to the fashion, beauty, and entertainment highlights that have made their way back, there are lots of celebrities who had a huge ’90s heyday and are still serving serious style now. Stars like Halle Berry, Naomi Campbell, and Winona Ryder have continued to inspire us, just like they did when we idolized them as teenagers.
Yes, we can sing the praises of Hailey Bieber, Lori Harvey
, and the Kardashian-Jenners all day, but before them came a crop of impossibly cool women who paved the way and showed us that there were so many different ways to be strong and smart and not take any sh*t.
WireImage / Steve.Granitz/INACTIVE
Drew Barrymore
Barrymore may have had a lot of ups and downs during her career, but the ’90s was when she really hit her stride. She was dating heartthrobs; she was wearing flowers in her hair; she was posing for Playboy; and she was palling around with Liv Tyler and Courtney Love. She was a real badass – and even though she’s a little more settled down these days, we just know Barrymore still has that rebellious streak.
FilmMagic, Inc / Jeff Kravitz
Winona Ryder
Ryder took the ’90s by storm with leading roles in “Edward Scissorhands,” “Girl, Interrupted,” and “Reality Bites.” She dated Johnny Depp and Matt Damon and rose to icon status thanks to her unique, dark performances and enviable pixie cut. Winona forever.
FilmMagic / Jeff Kravitz
Halle Berry
Berry was the go-to girl for ’90s movies with primarily Black casts – she starred in “Boomerang,” “Jungle Fever,” and “Strictly Business,” and it wasn’t long before mainstream Hollywood took note of her talent, beauty, and charisma on and off screen.
WireImage / Rose Hartman
Kate Moss
Back in the ’90s, Moss was drinking, smoking, and gracing the pages of Vogue. You know what Moss is doing today? Drinking, smoking, and gracing the pages of Vogue.
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Naomi Campbell
Campbell was walking runways left and right in the ’90s (usually alongside her BFF Kate Moss) and giving Black girls everywhere hope that they could become world-famous supermodels. Icon!
FilmMagic, Inc / Jeff Kravitz
FilmMagic, Inc / Jeff Kravitz
Liv Tyler
The truth is, Tyler was going to be cool no matter what she did. The daughter of model Bebe Buell and Aerosmith frontman Steven Tyler, she was not only ’90s rock ‘n’ roll royalty, but her roles in movies like “Empire Records,” “Stealing Beauty,” and “Armageddon” throughout the decade launched her into an entirely new stratosphere in Hollywood.
WireImage / Patti Ouderkirk
Gwen Stefani
Don’t act like you didn’t chop off all your white tank tops and jump around your bedroom while screaming along to “Just a Girl.” The best part is: Stefani is still just as cool, stylish, and ripped as she was back in the day.
WireImage / Kevin Mazur
Gwyneth Paltrow
Before she taught us about macrobiotic eating, vagina steaming, and conscious uncoupling, Paltrow was a ’90s movie darling, starring in films like “Seven,” “Great Expectations,” “The Talented Mr. Ripley,” and “Shakespeare in Love,” for which she won an Oscar in 1999. These days, she’s a lifestyle guru, mom of two cute kids, and BFF of Beyoncé. Not a bad evolution.
FilmMagic / Jeff Kravitz
Janet Jackson
By the ’90s, Jackson had fully stepped out of the shadow of her famous brothers and made a name for herself with hits like “Runaway,” “That’s the Way Love Goes,” and “Got ‘Til It’s Gone” and a starring role opposite Tupac Shakur in “Poetic Justice.” In one of her most daring moves, Jackson covered the Sept. 16, 1993, issue of Rolling Stone topless, with a man holding her breasts from behind.
WireImage / L. Cohen
Cindy Crawford
Crawford had already hit supermodel status by the time the ’90s started, but thanks to a steamy Pepsi commercial and a hosting gig on MTV’s “House of Style,” Crawford became a true household name. Those brows! That mole! Crawford has since retired from the game, but her lookalike daughter Kaia Gerber is carrying on her legacy.
WireImage / Kevin.Mazur/INACTIVE
Courtney Love
Is Love perfect? No. Is she a total badass? Absolutely. Nobody did babydoll dresses and smeared red lipstick like Love – and to this day, nobody looks as cool shredding their guitar with their foot up on the amp.
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Lisa Bonet
Bonet went from “The Cosby Show” and “A Different World” to marrying Lenny Kravitz and giving birth to their daughter, actor Zoë Kravitz. To this day, she’s still one of the poster children for the bohemian Black girl, and Zoë is totally following in her footsteps.
WireImage / SGranitz
Claire Danes
We didn’t know whether to love or hate Danes back in the ’90s: after all, this is the girl who got to romance both Jared Leto and Leonardo DiCaprio on screen, but she also just seemed like she’d be a really great BFF.
WireImage / Barry King
Natalie Portman
Portman made her film debut in 1994’s “Léon: The Professional,” and nabbed a major role (and tons of critical acclaim) in “Beautiful Girls” two years later. Before she won our hearts in “Closer,” “Garden State,” and “Black Swan” in the 2000s, though, Portman gave us literal goals when she took time off from acting to casually study psychology at Harvard University in 1999.
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Fiona Apple
Apple was only 18 when she dropped her debut single “Criminal” in 1996. The song’s video grabbed headlines for its sexual undertones – which were then considered controversial, but now seem ridiculously tame – and the following year, Apple nabbed a Grammy and gave a scathing acceptance speech when she won an MTV VMA, telling the crowd, “This world is bullsh*t.”
WireImage / Steve Eichner
Tyra Banks
Before she was “holding two photos” in her hand and picking the next America’s Next Top Model, Banks was stomping the runways for Chanel and Christian Dior and starring in Michael Jackson‘s “Black or White” video, as well as one of Will Smith‘s many love interests on “The Fresh Prince of Bel-Air.” She was also the first Black model to cover GQ, the Sports Illustrated Swimsuit Issue, and a Victoria’s Secret catalog. NBD.
WireImage / SGranitz
Chloë Sevigny
Sevigny started out as a Sassy model and intern thanks to her eclectic style, and made waves with her controversial, meaty roles in “Kids,” “Gummo,” and “Boys Don’t Cry” – the films made her an indie movie darling and a ’90s fashion favorite. Her influence still runs deep: in 2015, Sevigny released her own book, a memoir with personal photos and memorabilia detailing her unique Hollywood evolution.
WireImage / Steve Eichner
Brandy
Brandy had us singing along to her hits “I Wanna Be Down” and “Sittin’ Up in My Room” while also watching her on TV – her “Moesha” character, Moesha Mitchell, was everything we wanted to be: smart, quick-witted, and headstrong. Brandy inspired little girls even more in 1997 when she became the first-ever Black actor to portray Cinderella in a two-hour TV special with her mentor, Whitney Houston. Oh, and “The Boy Is Mine” with Monica? Classic middle school dance jam.
FilmMagic / Jeff Kravitz
Christina Ricci
Ricci’s breakthrough role as Wednesday Addams in “The Addams Family” films helped catapult her into teen icon status – how much did you love her as Roberta in “Now & Then” and Kat in “Casper”?
FilmMagic, Inc / Jeff Kravitz
Nia Long
Long starred on the big screen in classics like “Boyz n the Hood,” “Friday,” “Made in America,” and “Soul Food,” and also won our hearts as Will Smith‘s girlfriend Lisa on “The Fresh Prince of Bel-Air.”
WireImage / KMazur
Jennifer Aniston
Hello? “The Rachel”? Aniston had everyone running to their hairstylists to get the shaggy layered cut that she wore on “Friends,” and even though she’s since admitted that she found the style “cringe-y,” it still belongs in a beauty museum somewhere. While she was portraying Rachel Green on the hit NBC sitcom, Aniston was also starring in movies like “She’s the One,” “Picture Perfect,” “The Object of My Affection,” and “Office Space.”
AFP/Getty Images / BERTRAND GUAY
Kim Gordon
As one of the founding members of Sonic Youth, Gordon was a force to be reckoned with; she was a guitarist, songwriter, visual artist, and feminist badass. She and then-husband Thurston Moore inspired legions of fans with the band’s “no-wave” music, and Kim’s messy blonde hair, dark eyeliner, and rebellious sense of style became a ’90s-girl aesthetic.
FilmMagic, Inc / Jeff Kravitz
Tatyana Ali
Ali became a household name thanks to her role as Will Smith‘s young cousin Ashley Banks on “The Fresh Prince of Bel-Air.” She was sweet, talented, and got to hang out with Smith all day. Remember her 1998 song “Daydreamin’”?
FilmMagic, Inc / Jeff Kravitz
Sofia Coppola
Coppola starred in a few music videos with ’90s bands like The Black Crowes, Sonic Youth, and The Chemical Brothers and was featured as a model in teen magazines like Seventeen and YM. She cofounded the fashion brand Milk Fed in Japan, and was dating director Spike Jonze, whom she’d go on to marry in 1999. That same year, she made her feature film directing debut with “The Virgin Suicides.” By that time, the daughter of legendary director Francis Ford Coppola had become synonymous with some of the arbiters of ’90s cool: Karl Lagerfeld, Juergen Teller, and Marc Jacobs.
FilmMagic / Jeff Kravitz
Liz Phair
Phair’s 1993 album “Exile in Guyville” has been called “the most glorious, girly ‘f*ck you’ ever,” and even that seems like an understatement. It was a true feminist proclamation and one that couldn’t have come sooner, because we wanted to be as brazen, candid, and confidently flawed as Phair was. Would there have been an Alanis Morissette without Phair? Maybe not.
WireImage / Gregg DeGuire
Rosario Dawson
Dawson’s big screen debut was in the controversial (and disturbing) 1995 movie “Kids” along with fellow It girl Chloë Sevigny. She was the quintessential New York City kid: a street-smart, fast-talking fighter. These days, she’s still using her wisdom and outspokenness to champion causes close to her heart.
Britt stephens
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