Ron Galella, Ltd. Getty Images
The carefree, facile mastery of the ’90s will forever remain an aesthetic we crave. So our enthusiasm and nostalgia for the decade that brought us street style before street style blogs, and perfected high-waisted denim with absolutely no stretch, is no surprise—especially when it comes time for fall. From off-duty supermodels like Naomi Campbell to Princess Diana and Carolyn Bessette-Kennedy, the style icons of the 1990s feel more relevant than ever today. Ahead, get inspired by the looks of the decade that still hold up in 2020.
Cindy Crawford, 1991
The supermodel’s airport look—a black turtleneck, high-waisted denim, and a leather blazer—would look just as effortlessly cool in 2020.
Get the Look: Heidi Merrick leather blazer, $195, heidimerrick.com.
Tyra Banks, 1993
Denim on denim is a timeless look—one that was perfected in the ’90s. Take note from Tyra Banks and style an oversized denim shirt with your favorite pair of jeans.
Get the Look: Mango oversized denim shirt, $30, mango.com.
Kate Moss and Johnny Depp, 1998
Kate Moss proves the camel coat’s got major staying power. And knee-high boots paired with a miniskirt feels right on track for this season too.
Get the Look: Everlane cocoon coat, $187.50, nordstrom.com.
Princess Diana, 1994
Pretty much everything Princess Diana wore in the ’90s is cool again. But this blazer-and-turtleneck combo is the perfect fall look.
Get the look: Vince blazer, $465, vince.com.
Linda Evangelista, 1990
Another supermodel bombshell look that will never go out of style: this exact cropped blazer and high-waisted trouser ensemble could (and should) still be worn.
Get the Look: Carbon38 cropped blazer, $104, carbon38.com.
Carolyn Bessette-Kennedy and JFK Jr., 1996
From the headband and the oval sunglasses to the double-breasted coat and knee-high boots, Carolyn Bessette-Kennedy’s ’90s looks remain classics.
Get the Look: Slip silk headband, $69, dermstore.com.
Naomi Campbell, 1993
The decade wasn’t all grunge and minimal—Naomi Campbell’s colorful checked two-piece set was just the right amount of playful, and would absolutely kill it on the ‘gram today.
Get the look: Montce gingham pants, $128, montce.com.
Winona Ryder, 1991
Winona Ryder’s ’90s Outfits Forever: This concert tee, mom jeans, and leather blazer remain insanely cool to this day.
Get the Look: Re/Done jeans, $250, netaporter.com.
Cameron Diaz, 1998
Cameron Diaz’s high-low pairing of a chunky knit with a side-slit skirt feels very now. And the tiny bag and strappy minimal sandals? It girl favorites of 2020.
Get the Look: H&M turtleneck, $30, hm.com.
Halle Berry, 1994
This photo of Halle Berry could have been taken in 1994 or 2020. The long leopard coat, black turtleneck, and straight-leg jeans? Sign us up, please.
Get the Look: Jacquemus Thika coat, $768, 24s.com.
Kate Moss and Naomi Campbell, 1993
It’s no secret that the naked dress remains a celebrity favorite to this day. But in ’93, Kate the Great perfected the look in a sheer slipdress and black undies.
Get the Look: Lovers + Friends dress, $158, revolve.com.
Sarah Jessica Parker, 1999
From the early years of the decade to her time as Carrie Bradshaw, SJP rocked a number of looks that were right on par with the trends. But this jacket-and-skirt combo would look just as good—if not better—in 2020.
Get the look: Michael Michael Kors cotton skirt, $97.50, netaporter.com.
Jennifer Lopez, 1995
A floral maxi dress paired with a leather jacket? Nothing is more ’90s, and JLo’s take on the look still feels stylish.
Get the look: Free People Charisma slip dress, $80, freepeople.com.
Cindy Crawford, 1990
Crawford’s leather jackets deserve their own fan account—this brown oversized jacket styled with a black turtleneck and knit miniskirt should be on all our mood boards this fall.
Get the Look: Low Classic belted blazer, $209, farfetch.com.
Drew Barrymore, 1991
Cardigans are back—and there’s no better way to style them this season than ’90s Drew.
Get the Look: LoveShackFancy Folley cardigan, $260, mytheresa.com.
Tyra Banks, 1996
Banks’s airport look from 1996 is one that 90 percent of the population (including a Hadid or two) still rocks to this day. Denim jacket, Calvin Klein logo tee, and dad sneakers: The ’90s uniform is back in full force.
Get the Look: Levi’s denim jacket, $79.50, levis.com.
Christy Turlington, 1991
The Versace bombshell look of the ’90s—perfected by the Big Six—is just as enviable today. We’re ready to petition for Versace to bring back Turlington’s bright yellow skirt suit and chain belt.
Fran Drescher, 1990
The Nanny remains a fashion icon to this day. And her penchant for leopard? It’ll never go out of style.
Get the Look: Nanushka leopard pants, $276, mytheresa.com.
Princess Diana, 1995
Nobody has pulled off the sweatshirt-and-bike shorts trend of 2020 quite like Diana originally did in 1995.
Get the Look: Aritzia bike shorts, $38, aritzia.com.
From her sportswear to her iconic Tommy Hilfiger looks, Aaliyah spearheaded many of the decade’s trends. But one of her most underrated outfits? This oversized leather jacket-and-cargo pant combo that would look just as on trend in fall 2020.
Get the Look: The Range Tide pants, $210, shopbop.com.
Halle Berry, 1994
Berry serving these high-waisted shorts, a white crop top, and lace-up boots will never get old.
Get the Look: Frye Veronica boots, $278, nordstrom.com.
Cindy Crawford, 1994
The maxi skirt is back. Why not take a page from Crawford’s book and try the piece with a knit sweater and mules?
Get the Look: Zara printed midi skirt, $70, zara.com.
Iman and David Bowie, 1994
Iman proves a checked skirt suit and turtleneck will always be a major look.
Gwyneth Paltrow, 1996
Leather pants—a staple of the decade—are slowly inching their way back. Try the look in monochromatic form with a simple black turtleneck à la Gwyneth Paltrow.
Get the Look: Nanushka leather pants, $445, shopbop.com.
Kate Moss, 1995
Though Moss’s ’95 look may have been originally channeling the 1960s, the minimal black-and-white combo remains a wardrobe classic.
Reese Witherspoon, 1997
An LBD and knee-high boots? We’re ready to bring back this look. Add a jacket over top for fall/winter styling.
Get the look: Urban Outfitters minidress, $70, urbanoutfitters.com.
Naomi Campbell, 1998
Campbell’s white-and-black airport look accessorized with Louis Vuitton luggage will always be a favorite. Don’t forget the oval sunglasses and anklet.
Get the look: Louis Vuitton circle bag, $4,850, us.louisvuitton.com.
Claudia Schiffer, 1992
We’re still a sucker for a
sweaterdress—and the ’90s supermodel proved that the look can be sexy, too, in this leopard off-the-shoulder iteration.
Get the Look: Reformation Sabine dress, $118, shopbop.com.
Carolyn Bessette-Kennedy and JFK Jr., 1997
If you’ve ever doubted the impact of a classic white button-down shirt, let Bessette-Kennedy prove you wrong time and time again. The style icon proved less is more and always chic.
Get the Look: Uniqlo button-down shirt, $30, uniqlo.com.
Jennifer Lopez, 1990
Expect to see leather pencil skirts in full force this season. And take note from J.Lo by styling them with a knit sweater for the perfect texture contrast.
Get the Look: A.W.A.K.E. Mode leather skirt, $151, matchesfashion.com.
Kate Moss and Naomi Campbell, 1991
It’s hard to even fathom attempting to re-create Moss’s and Campbell’s many party looks of the era, but these iconic outfits serve as a reminder to have some fun with your going-out looks.
Halle Berry, 1999
Berry brought a little French flair to her black suit with a floral neck scarf.
Get the Look: Madewell silky neck scarf, $15, madewell.com.
Christy Turlington, 1990
Let Turlington remind you that an oversized tan suit and white under tank will never go out of style. Make sure the pants are high-rise.
Get the look: Billie the Label Gloria pants, $168, verishop.com.
Jennifer Aniston, 1999
This 1999 fit could easily be re-worn by Aniston in 2020—boyfriend jeans, a black cardigan, and flatform sandals.
Get the look: Toteme blue jeans, $265, ssense.com.
This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at piano.io