The '90s Style Icon Who Is Still Impacting Modern Fashion In A Major Way

Say what you want about '90s fashion, but it might actually be one of the most versatile, varied, and exciting decades. It brought in a smorgasbord of clothing trends, from flannel shirts and baggy pants to plaid skirts and platform sneakers. While we can certainly point to pop culture influences like Cher from Clueless and Rachel Green from Friends, there were also the real-life celebs who served as ‘90s style icons and whose marks are still left on fashion today.

Take the recent evolution of normcore-meets-athleisure. That whole crop top and sweats look didn’t just come out of nowhere. Many stylists and fashion insiders point to the late singer Aaliyah for its origins. The sporty and casual approach to dressing contained a certain vibe of “controlled sexuality,” as stylist Jeanne Yang puts it; something that the singer helped pioneer, along with other ‘90s icons like Madonna and Janet Jackson. “I mean, most of the people who are [emulating the look] now weren't even born,” says Yang to TZR.

There's also the looks made famous by another singer the world lost too soon: Selena Quintanilla. The legendary Tejano artist was famous for her voice and ability to perfect quintessential ‘90s trends together into a fashionable cocktail. From bedazzled bra tops with high-waisted denim to frilled tie-front blouses layered under bulky leather jackets, Quintanilla embraced the decade’s boldest looks fearlessly and never missed a beat.

And then there's the decade's moody ingenue, Winona Ryder. Pre-millennium, the Beetlejuice actor managed to strike the perfect balance of goth-meets-grunge in such a way that still felt wearable and glamorous. She spearheaded the oversized power suit movement as well as the still-relevant combat-boot-and-gauzy-dress combo.

Yes, in the world of ‘90s fashion, there are so many stars who’ve championed some of the most influential trends that are still relevant today, but have flown under the radar — until now. Ahead, nine ‘90s style icons who continue to inspire wardrobes all over.

'90s Style Icons: Aaliyah

Tim Mosenfelder/Getty Images Entertainment/Getty Images

Athleisure may be a popular look with the Hadids and Jenner sisters, but let’s give credit where credit is due: the one and only baby girl, Aaliyah. In the '90s, the R&B singer was known for pairing Tommy Hilfiger bandeau tops with matching boxers peeking out from low-slung athletic pants, sometimes alternating with strappy bikini tops and PVC or camouflage. On the red carpet, she’d go edgy glam, with leather bottoms or leopard-print gowns.

Celebrity stylist Mikiel Benyamin, whose clients include Keke Palmer, Bella Thorne, and Normani, praises Aaliyah for pioneering the look. “At the time, it was so daring how she wore baggy pants and barely-there tops,” says Benyamin, who draws inspo from Aaliyah's style for all of his clients. Yang credits Aaliyah’s stylist Derek Lee for being on the forefront of creating the athleisure style the singer was known for (long before it became the household term used today). “It was kind of like ‘real’ clothing, where it was like styling without being styled, and it worked for Aaliyah,” says Yang.

'90s Style Icons: Selena Quintanilla

Vinnie Zuffante/Archive Photos/Getty Images

Tejano singer Selena Quintanilla was just crossing over to the American music scene when she tragically died — but she had already left a lasting mark on pop culture and fashion. (She even had her own clothing line and boutiques!) The pieces that made up Quintanilla’s distinct style are still popular today: tie-front and ruffled tops, hoop earrings, cropped jackets, and the clothing item she's most associated with, the bedazzled bra. Or, as Selena (Jennifer Lopez) tells her dad in the 1997 movie Selena, “It’s just a bustier!”

Gentefied costume designer Jen Martín says she was inspired by Selena when coming up with outfits for the character of Ana, who is an artist, and referred to that famous scene in the movie. “Both artists play by their own rules and aren’t going to let society dictate what they should or shouldn’t wear,” she says. LaLa Romero, co-owner of fashion and beauty brands Bella Doña and Sweet Street Cosmetics, also points out the effect that Quintanilla had on body image: “I think even bigger than any outfit or beauty look, Selena and her booty really created a super important convo about body positivity in fashion and beyond. I grew up with a big butt, before they were popular in the mainstream. Her body confidence was super empowering in the ‘90s for young girls with curves.”

'90s Style Icons: Madonna

Gie Knaeps/Hulton Archive/Getty Images

From the moment Madonna started her musical career, she was an icon. Who can forget her “Like a Virgin” VMAs performance, where she rolled around onstage in a white wedding dress, accessorized with a “boy toy” belt buckle, wrists stacked with bracelets? But it was the 1990s that would elevate her to fashion legend status. “When I think of Madonna in the '90s, I immediately think of the Jean Paul Gaultier cone bra bodysuit from the ‘Blonde Ambition’ tour,” says stylist, designer, and TZR's editor-at-large Rachel Zoe. “It was such a moment in time.”

While the cone bra didn’t suddenly become a necessity in everyone’s wardrobe, it certainly helped usher in the underwear-as-outerwear trend that continues to be popular today. The singer continued to experiment with cutting-edge fashion, from 1950s glam to military-inspired looks, and beyond. “Madonna is truly the queen of reinventing herself, and her fearlessness opened doors for future female artists to express themselves through provocative style and music," adds Zoe.

'90s Style Icons: Gwen Stefani

Rick Loomis/Los Angeles Times/Getty Images

The first time many ‘90s kids heard No Doubt’s “Just a Girl” was in Clueless, when ‘90s movie fashion maven Cher Horowitz picks Dionne up during the famous “Shopping with Dr. Seuss?” scene. Little did we know, Gwen Stefani was about to become a style icon of her own. The SoCal-born lead singer invented her own version of girly, punk rock style, pairing Dickies and Adidas pants with furry coats, cropped tank tops and exposed bedazzled bra straps. And who can forget her equally memorable hair moments in those early years, often done up in 1940s victory rolls, topped off with her signature red pout? “I had to be a little bit tomboy with a little bit glamour,” Stefani told Vogue in 2019. Later, the singer would turn her love of fashion into an empire with her clothing line, L.A.M.B.

Clueless costume designer Mona May liked how Stefani used vintage in her outfits, blending her tomboy leanings with pinup style. “She was really kind of open and fluid with her style,” says May. “I love looking at her plaid stuff, she just took it to another level."

'90s Style Icons: Winona Ryder

Ron Galella, Ltd./Ron Galella Collection/Getty Images

Quirky (and fashionably memorable) roles in Heathers, Beetlejuice, and Reality Bites helped make Ryder the “It girl” of the decade. Her style was an eclectic mix that teetered on the edge of casual-grunge-meets-goth-glam, which Yang describes as “elegant without looking too elegant” and “relaxed without looking too relaxed,” noting that it’s something she sees as being really influential today. Ryder’s everyday look in the '90s consisted of oversized blazers, baggy slacks, motorcycle jackets, and T-shirts, while her red carpet looks were a bit more traditionally feminine: flapper-inspired numbers, bustier gowns, and lace or velvet floor-length dresses.

And when it came to iconic hairstyles — move over, “The Rachel” — no one pulled off the pixie cut quite like she did. “Winona Ryder was the 1990s celebrity girlfriend poster girl,” says PAPER’s editorial director Mickey Boardman. “She was a gorgeous movie star, but dressed like the cool girl next door in denim, a leather jacket, and a rock 'n’ roll T-shirt you got the feeling she borrowed from her rock star boyfriend.”

'90s Style Icons: Janet Jackson

Steve Azzara/Corbis Entertainment/Getty Images

Janet Jackson didn’t wear cone bras like Madonna, but she had her own fashion-making moments in the ‘90s, particularly with accessories. She helped propel the choker necklace trend, popularized the boxer braids look, and made it so wearing statement earrings (preferably in the shape of a key) was cool as hell.

She also wore a crop top like no one else. In fact, Brittany Spanos, a senior writer at Rolling Stone, thinks Jackson’s style preferences may have depended on her impressive abs. “Her crop tops were a consistent presence and her fashion sense from that decade was clearly influential on Britney, Aaliyah, Christina, and their whole class of pop and R&B princesses,” says Spanos. “It was also so reflective of who she was musically at the time: comfortable in her own skin both as a young woman and a superstar free of her brother's immense musical shadow.”

'90s Style Icons: Lil’ Kim

Ron Galella/Ron Galella Collection/Getty Images

Women hip-hop artists have always been the harbingers of fashion trends. But while Salt-N-Pepa, TLC, and Queen Latifah had their own influential style, Lil’ Kim brought something unique to the table. While many of her colleagues embraced traditionally masculine style, Kim was celebrating her sexuality, proudly showing off her body in leopard-print bikinis, candy-colored fur, and that lilac, mermaid-patterned catsuit with a matching chest pasty that made for an unforgettable moment with Diana Ross at the 1999 MTV VMAs.

When it comes to influence, Lil’ Kim is unmatched. “The way that Kim took Chanel logos and stenciled them on her hair. Everyone remembers that. Even Beyoncé recreated it for Halloween,” says Benyamin. And she’s not the only one: Cardi B, Mulatto, Rihanna, and anyone who appreciates colorful fur has paid homage to Kim.

'90s Style Icons: Courtney Love

Ron Davis/Archive Photos/Getty Images

A satin slip usually conjures up the idea of delicateness; something that should be delegated to a private moment, or the hushed corners of a bedroom. Singer Courtney Love managed to subvert this idea in the ‘90s with her messy, punk rock interpretation of the slip, when she styled it with black fishnets, a leopard-print coat, baby barrettes, and smeared red lipstick (and she did the same thing with babydoll dresses).

And while it might have been classified as edgy, it was also accessible to many then, and is still today. “When it comes to iconic fashion images of the ‘90s, nothing can top the famous shot of Courtney Love and Amanda de Cadenet out on the town, adorable and messy in matching 1940s dresses, tiaras, and red lips. It was rock 'n’ roll meets vintage, meets glamour girl, meets the Academy Awards,” says Boardman.

'90s Style Icons: Drew Barrymore

Steve.Granitz/INACTIVE/WireImage/Getty Images

Throughout most of the '90s, Drew Barrymore was seen as a good girl gone bad, starring in movies like Poison Ivy and flashing her breasts at David Letterman without warning. Her clothing style varied, from double slip dresses to boyish jeans and cropped tees. Mona May, who worked with Barrymore on Never Been Kissed, The Wedding Singer, and Santa Clarita Diet, says she has always loved how Barrymore has a joie de vivre that always comes out in her style. “She's really like a free spirit in a sense. She’d wear these little, spaghetti-strap dresses and put daisies in her hair, but she was also a little bit of a tomboy, so she would wear Doc Martens,” says May. “I think, to this day, there's something about her that people are so drawn to, it's just a kind of sweetness that she has.”