“Do you remember how Destiny’s Child used to wear matching outfits that [Beyoncé’s] mom made?” Stylist Kate Young cut straight to the heart of the matter.
Of course. How could one forget?
The custom pieces by Tina Knowles-Lawson are among the looks that defined fashion at the turn of the century, a time when the world was privy to Lil’ Kim’s seashell pasty, an accent on her breast-baring jumpsuit. Sarah Jessica Parker epitomized Carrie Bradshaw in the instantly iconic John Galliano for Dior newsprint slip dress; Samuel L. Jackson was everywhere with his signature Kangol hats; Mariah Carey bedazzled in her butterfly halter. Jeans were irrationally low-rise, midriffs were often bare, and brands such as Sean John and Baby Phat, born of hip-hop, quickly rose to cultural dominance.
Now, two decades after Björk turned up to the Oscars as a swan, Young, fellow stylists June Ambrose and Misa Hylton, Pulitzer Prize-winning fashion critic Robin Givhan, and writer Evan Ross Katz look back on the trends and red-carpet moments that defined and reflected an era.
Streetwear had long had a flair for the dramatic, but much of the runway fashion that predated 1999 was decidedly minimal. As hip-hop grew in popularity and a small group of designers planted roots in Los Angeles, this started to change.
ROBIN GIVHAN (senior critic-at-large, The Washington Post): The mid-’90s had seen a period of minimalism and heroin chic—a reserved and a little bit bleak sensibility. [1999–2001] was a much more exuberant, ostentatious time for fashion. It reminds me of what we refer to as “ghetto fabulous” and the rise of hip-hop in a very upmarket kind of way.
KATE YOUNG (stylist and host of Hello Fashion on YouTube): There was a guy named Henry Duarte who was making jeans that were really cool, and Rick Owens used to sell at Maxfield [in L.A.] then. He made tank tops that were really long. It was cool to wear boot-cut jeans with really long tank tops and tiny cardigans. Drew Barrymore, Mischa Barton, Cameron Diaz…they all wore those L.A. designers that I, as a New York fashion person, was really excited about. There were girls wearing stuff that we didn’t see in New York because it wasn’t [considered] fashion, that I thought was really cool.
While musicians often worked with their record label’s stylists and image consultants, for the most part, actors were still dressing themselves.
YOUNG: People didn’t really have stylists, so a lot of [celebrities] were wearing their own clothes; clearly just a dress they bought off the rack in Hollywood somewhere. Or if they were a musician, there was a lot of custom from costume designers.
JUNE AMBROSE (stylist and creative director): [Luxury brands] knew nothing of us. It seems so normal now that the big fashion houses in Europe have embraced urban and pop culture the way they have, but at the time, the idea of bridging music and fashion was foreign. They didn’t have the vision to see that this was an opportunity for them to market and brand, and to touch consumers through using these artists as muses. I had to start with costume designing to get their attention.
GIVHAN: The color and the bedazzlement, the showing off of the midriff and the skin, it was definitely a huge, not just look-at-me, but look-at-my-success period.
Low-rise jeans, exposed thongs, and handkerchief tops—like the one worn by Jennifer Aniston to the SAG Awards in 1999—became popular trends among teens and young adults. Meanwhile, on the opposite side of the style spectrum, Hillary Clinton was reshaping the style status quo for women in business and politics.
YOUNG: Juicy Couture came out with the lowest-rise jeans [ever]. They were way below your hip bone—like way, way, way. And then you would wear a crop top with that. [And] that thong trend was a Tom Ford for Gucci thing. People started doing it after he showed it.
EVAN ROSS KATZ (writer and host of the Shut Up Evan podcast): There’s a line from RuPaul’s Drag Race where Michelle Visage says, “It’s a piece of fabric,” and that could be said of the [handkerchief top].
YOUNG: Galliano at that time was the coolest thing you could possibly wear. And all those Kate Moss metal dresses, all the girls wearing them to the Met Ball—the slip dresses with the buttons and the bias cut. That was as chic as you could possibly be.
GIVHAN: The whole spectrum of women in politics goes from the ’80s, when female senators couldn’t even wear pants on the Senate floor, through Hillary Clinton campaigning for the Senate in black pantsuits and running for president in a rainbow wardrobe of pantsuits, all the way to Kamala Harris now, whose daily uniform is basically a dark pantsuit. Hillary Clinton rarely wore trousers as first lady [so] that pink pantsuit was game changing. To me, it was warrior clothing.
On March 21, 1999, Gwyneth Paltrow arrived at the Oscars in a bubblegum pink ball gown by Ralph Lauren. Céline Dion opted for a white John Galliano tuxedo, worn backward and accessorized with a matching fedora.
GIVHAN: So much effort and attention and energy goes into those looks. It was really surprising that [Paltrow’s dress] looked like it had been pulled off the rack and not really fit for her.
YOUNG: I remember thinking, Why didn’t they sort out that bust? It just didn’t fit, and that really confused me. But looking back on it now, I think it’s amazing. It’s a great iconic Oscars look.
KATZ: I would speculate that that dress worn today would receive a lot more criticism because it’s not properly steamed. And I think that it would perhaps be perceived as overly simple. I love the amount of chest that is exposed, and that the straps are so close to the shoulders. And bubblegum pink on a red carpet, it just has a pop to it.
YOUNG: I love Céline Dion, but I really hated [the backward-tux moment]. I hate a fedora, so it’s really hard for me to get past that. [The suit] is actually quite chic, but the fedora and sunglasses, it’s too much.
KATZ: Céline Dion is such a certified style icon in 2021, but 20 years ago that wasn’t the case. People used to scoff at her craziness and in 2021 it’s celebrated, as it should be.
Lil’ Kim’s Misa Hylton-designed jumpsuit instantly became one of the most recognizable looks of all time when the rapper walked the red carpet at the MTV Video Music Awards on September 9, 1999.
MISA HYLTON (stylist and designer): Missy Elliott actually gave me the idea for that look. I was hanging out at her house one day, and she was like, “You know what? Kim is such a fly bitch. If I was Kim, you know what I would do? I would just have one titty out.” So I just made a mental note. The next big event we had was the 1999 MTV Video Music Awards, [and] that idea Missy gave me was the inspiration for the jumpsuit. I wanted to make it really beautiful and pretty; feminine and flirty and colorful. So I purchased Indian bridal fabric.
AMBROSE: For me, it was such a liberating moment for women. It was a Gloria Steinem moment. [Kim was] owning her body and her breasts. [It made me think of] marching in the streets in the ’60s...women with their tops off...big signs that said, “We are women, hear us roar!”
GIVHAN: Looking back, it certainly feels like it was a precursor to Rihanna wearing a bedazzled fishnet dress to the CFDA Fashion Awards, and Beyoncé wearing basically a glittery scrim to the Costume Institute Gala; a whole series of A-list women who wore gowns that were a hair’s breadth away from them being totally naked.
Despite a growing public appetite for all things celebrity—including what stars were wearing—a number of major fashion houses were still reluctant or unwilling to work with them. As a result, Ambrose and Hylton continued to design custom looks for their clients, as did Tina Knowles-Lawson for Destiny’s Child.
YOUNG: Fashion and celebrity were not friends yet. Fashion really held itself apart; it was really snobby back then.
KATZ: At the time, major fashion houses were not lending to people of color, or to bigger people. And it still exists today. There’s a lot of discrimination in terms of how clothes are resourced to celebrities.
AMBROSE: I didn’t have the luxury of calling in a look. [Design houses] wouldn’t even take my calls back then. So what are you supposed to do? You have to figure it out.
KATZ: Tina Knowles-Lawson deserves her flowers. It’s worth paying respect to her for saying, “I don’t have the resources available to me to get what I want, so I, myself, will become a resource for this group.”
HYLTON: By [2000] I had begun to establish relationships with [designers], because Lil’ Kim was the hottest thing out, and everybody wanted a piece of her. We would sit front row at fashion shows, Donatella Versace was flying us to her house on Lake Como…. Now, if you go back a few years, it was very difficult.
AMBROSE: Design houses only started to talk to us when they saw the impact we were having on retail, consumers, and pop culture. We didn’t have to go back and have a conversation with them, but I thought it was important for inclusivity that we were all speaking together as one. And it was for that reason that I was open to collaborating with designers and working with them. Also, they had superior tailoring and access that we didn’t have.
Soon, red carpets seemingly usurped the awards shows themselves, with much of the discourse surrounding the events being about fashion.
GIVHAN: With hindsight being 20/20, looking back, you sort of realize that early on, the goal on the red carpet was to find a dress that looked really lovely on you and to not be embarrassed. That was sort of what allowed designers like Armani and Valentino to rise to the occasion, and the question of “Who are you wearing?” became the thing.
KATZ: [That time] was really peak worst-dressed-list culture. It was peak Joan Rivers on the red carpet. There was lots of criticizing people, and often women criticizing women. Though it would often be about the clothing, it could easily meander into criticism of bodies.
GIVHAN: In recent years, there’s been this pushback in asking—particularly female actors—about their attire, and the glam cameras that scan the body from head to toe, and how demeaning that is. You look back and realize that it was in many ways, these very young actresses who were placing their body at the center of the story. But then you could also argue that it was a matter of empowerment, that they could own the red carpet and own their sexuality and physicality.
The plunging Versace dress Jennifer Lopez wore to the Grammys on February 23, 2000, garnered so much interest that it inspired the creation of Google Images. While women commanded the bulk of the red-carpet attention at the time, men were also taking fashion and personal style seriously.
YOUNG: I really liked the way Matt Dillon used to dress. There was a Rat Pack thing going on. [Leonardo] DiCaprio and Matt were wearing high-waisted trousers, and I thought that was great. And I loved their haircuts. Leo’s haircut from the ’90s is the greatest thing I’ve ever seen.
KATZ: Keanu Reeves [in all black] is a great example of the fact that there’s a blueprint that’s existed. Timothée Chalamet is not inventing men caring about how they look on a red carpet. Keanu looked like a capital-S star in that look. It’s incredibly chic.
AMBROSE: That was a huge risk because it didn’t look like the typical Hollywood movie star black-tie moment. He forwent the bow tie for the black tie and then did a black shirt with a [suit]. Black on black on black on black on black.
GIVHAN: During that period, the real peacocking for menswear was really coming through the world of music and hip-hop, and men of color.
Early 2001: Britney Spears and Justin Timberlake wore matching denim ensembles to the American Music Awards on January 8. A few months later, Björk had her moment.
YOUNG: [Those Britney and Justin looks] were horrific; just so bad. I couldn’t believe it. Now I think it’s so funny, and I think that’s why it stays around, because it’s hilarious. I think Posh Spice, Victoria Beckham, clearly had the best P.R. in the world, because she and David Beckham used to [dress alike] too, and you never see those images referenced. Her wedding [in July 1999] is what I look at to cheer myself up; it’s the best. The crown with the hair poking through, it’s amazing. There was so much joy for me in that image.
AMBROSE: Anything that looks like a costume and is outlandish and reckless on the carpet gets 10s across the board from me. But I mean, it was Björk, what did we expect? She was [that era’s] Gaga.
GIVHAN: It certainly put Marjan [Pejoski], the designer, into people’s brains. It was one of those moments that hearkened back to the pre-Giorgio Armani dominance of the red carpet—the predominance of professional stylists—when a lot of celebrities worked on their own. It had the kind of peculiar eccentricity that you tended to see then. But I think it was also the beginning of the realization that the red carpet was not just a place where you could get on the best-dressed list, but it was also a place where you could really establish a brand, and it could be seen as a kind of personal advertising. So-called good style was not necessarily the ultimate goal. The ultimate goal was about being memorable.
Today, says Ambrose, “we’re gorging on fashion as opposed to slowly tasting it”—one of the many influences of the internet and social media. Both have changed how quickly and often we see runway shows and red carpets, and democratized access to fashion.
KATZ: There were less images being shared, so there was an importance to a red carpet. That’s not to say that the importance doesn’t exist today, but because there’s such a ubiquity of red carpets [and] paparazzi photos and Instagram photos, we see images all day.
YOUNG: I feel like [what was popular then] is what the young girls wear now…. Look at how Hailey Bieber wears crop tops every day…I love the runway fashion of that time; all the minimal clothing. Calvin Klein and Jil Sander were amazing then. I love a slip dress, a slide, no makeup and thin eyebrows. I think it’s chic.
GIVHAN: When I think about that period, the first thing that comes to mind is the rise of Gucci as this sort of juggernaut of a global brand that changed the fashion business.
YOUNG: There was no Instagram [or online shopping], so you had to shop where you were. You couldn’t buy stuff on the internet that was from Denmark because you liked some girl in Denmark’s personal style.
KATZ: In the fashion history books, I don’t know if we’re going to be talking much about 2021, COVID aside, the way that we do [1999–2001]. There was such fearlessness and lack of inhibition. And even though the worst-dressed lists no longer exist [to the extent that they once did], people are fearful of rocking the boat in any kind of way.
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