The Entertainmentification of Fashion

It was 1996, and Salma Hayek couldn’t stop laughing.

The actress, then 29, was lying on a kitchen table in a siren-red gown by Pamela Dennis. A spotlight meant to highlight the satin folds of her dress was blinding her eyes instead. A makeup artist was trying to ensure her mascara didn’t smear as she squinted. A hairstylist kept teasing her curls into bigger and bigger spiral poufs. And a wind machine, meant to amplify the star’s dramatic look, had begun blowing tiny bits of smoke instead.

“I don’t know what’s going on, guys,” Hayek joked from her precarious pose on the table. “But I know it is not great!”

The ensuing photographs, however, were great. Shot for InStyle’s September fashion issue, the pictures captured a candid, joyful Hayek just coming into her own as a movie star. Sandwiched between portraits of Halle Berry and Matt LeBlanc in a photo shoot titled “What’s Sexy Now,” the image made an easy case for Hayek as a member of Hollywood’s new ruling class, and inspired InStyle’s editors to give the actress her own cover in January 1998; it was the first time a Mexican actress ever fronted a mainstream American fashion magazine. “It’s very dear to me,” Hayek has said of the memory. “I felt very, very honored.” 

“We didn’t realize what we were doing was unusual,” says Phillip Bloch, the stylist for Hayek’s early InStyle shoots. Bloch also procured Hayek’s ivory Armani gown and tiara for the 1997 Academy Awards, which she wore with an updo and a smear of aqua eyeshadow to channel—and subvert—Audrey Hepburn’s archetypical Breakfast at Tiffany’s glamor, along with InStyle covers and red carpet looks for Sandra Bullock, Jada Pinkett Smith, and Jennifer Lopez. “We didn’t have words like ‘groundbreaking’ or ‘diverse’ or ‘directional,’” he says. “We just knew that we were having so, so much fun.”

Bloch’s work at InStyle came at a pivotal moment for the fashion industry, one when the worlds of runways and red carpets were converging with a force and magnitude previously unseen. To be sure, some celebrities had cultivated their own relationships with various fashion forefathers—Grace Kelly and the Hermès dynasty in the ‘50s; Hepburn and Hubert de Givenchy in the ‘60s; Cher and Bob Mackie in the ‘80s. “But the reality is, most celebrities would still go to Maxfields and buy their own Oscar dresses until stylists came along,” Bloch says, noting that while legacy fashion magazines put one or two actresses a year on their covers and saved the rest for models like Kate Moss, “InStyle really brought about the change” that saw movie stars taking over newsstands.

Fashion and celebrity would soon be friends with very lucrative benefits. But before they could become besties, they had to start hanging out. 

Access Granted

InStyle was born in 1994—the same year that the TV tabloid show Extra hit airwaves, and that Joan Rivers hosted the first-ever red carpet show for E! Entertainment with her daughter, Melissa. (It was for the Golden Globes.) An offshoot of People, the debut cover of InStyle starred Barbra Streisand and, though Bloch styled it—along with nearly 100 others during his tenure as the magazine’s West Coast fashion editor—he wasn’t listed in the magazine’s credits. “We didn’t have titles like ‘celebrity fashion stylist’ yet,” he says. 

Alongside a heavy emphasis on lifestyle coverage (e.g. recipes from Julia Louis-Dreyfus and Roma Downey), InStyle put the spotlight on designers like Todd Oldham and Jean Paul Gaultier, letting readers see catwalk pieces as worn by real people—or at least on celebrities with “everywoman” vibes, like Mary Tyler Moore and Daisy Fuentes. “InStyle was one of the first magazines that actively turned fashion into entertainment,” says Cynthia Rowley, whose 1999 runway show was sponsored by the magazine. “They put our catwalk in the middle of Grand Central Station, which was huge for a small brand like mine back then. And they livestreamed the show to all the commuters coming through the train station as it was happening. This was before livestream was even a word.”

InStyle also gave the world its first peek at some of Hollywood’s most radiant “nepo babies”—before that was even a word. (Okay, two. It’s two words…) An August 1995 issue has Andie MacDowell holding a 9-month-old Margaret Qualley. The same issue featured film director Zelda Williams with her father, the late Robin Williams, and actor Jack Quaid with his mother, Meg Ryan. Kate Hudson, then-16, even shared a 1996 cover with her mother, Goldie Hawn, in a white tank top and loose Levis jeans. 

But fashion and entertainment weren’t yet BFFs—more like acquaintances who knew they really liked each other, but couldn’t quite figure out how to hang out one-on-one. Their imminent closeness was forged by the same thing that makes most of us fall in love with someone: Really good taste in TV shows.

The Runway Will Be Televised

As color photography and printing became cheaper in the 1980s and ‘90s, magazines and newspapers experienced a major boom, and celebrity tabloids like US Weekly in the US and Heat in the UK chronicled the daily lives of stars with increasing frequency. But it was the explosion of cable TV that really pushed high fashion into the national mindset. 

“Moviegoers, for the most part, were less taken with screen performances than with the drama of stars’ private lives,” writes David Friend in his book The Naughty Nineties. Which meant, “to many Oscar-night viewers, all that began to matter was the clothes.” As reviewed live on-air by the Riverses, those clothes “helped turn the mere act of showing up somewhere into a pastime, even a profession… It was Joan Rivers who formalized the riff, creating a sort of fashion rap.” Joan’s televised Oscar fashion critiques sometimes went too far, commenting on stars’ weight and breakups as well as their clothes. But her scathing wit and fiercely fast mind were undeniable, and helped the Oscars hit their apex viewership in 1998, when more than 58 million people tuned into the show and its eye-popping fashion antics, including Sharon Stone in her legendary Gap white shirt and Vera Wang silk skirt. (The look was later referenced by Zendaya in a near-identical Valentino Haute Couture look circa 2022.)

In addition to celebrity red carpet videos, music videos became a driving force of ‘90s style, which put MTV in a unique position to influence its core audience of teens and young adults. 

“1994, ’95, ’96, ’97… that was like the height of music video fashion,” recalls June Ambrose, the designer and creative director who created looks for Missy Elliott, Jay-Z, Mary J. Blige, Busta Rhymes, and other hit artists. “We were crafting our own narrative storytelling, really taking things out of context, creating our own kind of subcultures. It really was about changing the perception of hip hop music, Black art, Black music.” Through national outlets like MTV, hip-hop music became pop music, and hip-hop celebrity fashion became mainstream American fashion: “I remember going to Bloomingdale’s once, right after [Missy Elliott’s] Rain came out. This guy was asking a salesperson if they had big, leather tracksuits. Then someone else asked if they had a shiny, puffy tracksuit. And those were things I had built for music videos because I couldn’t buy them at Bloomingdale’s!”

Ambrose was astonished. Music videos were turning singers and rappers into fashion influencers, albeit ones who had no idea that “influencing” could be a job of its own. “They didn’t know yet that people were dying to dress like them,” Ambrose says. “But I saw it on that sales floor.”

At the same time, MTV’s House of Style, which first aired in 1989, turned fashion stars into some of MTV’s first reality TV characters, as New York luminaries like Isaac Mizrahi and Betsey Johnson were beamed into people’s living rooms alongside Madonna and Michael Jackson. “To this day, when I mention House of Style, people go crazy,” says Matthew C. Mills, one of the show’s original producers. “It influenced how so many young people learned about fashion.”

A junior producer at the network in the early ‘90s, Mills was pulled onto the show because studio executives believed he’d have an easy rapport with one of its stars, model and actress Molly Sims. “My boss was like, ‘You’re from Texas. She’s from Kentucky. You’re both really nice. Go figure it out,’” he says. “I should say, at the time, I knew nothing about fashion.” Days later, Mills was standing in the shallow end of the Gulf of Mexico, holding cue cards for Sims as she talked about bathing suits in Cancun, and later helped her develop the House of Style sequel, Mission: Makeover. “We were gamifying fashion before Project Runway,” he says.

Over the next few years, Mills filmed fashion segments with everyone from Britney Spears to Donatella Versace, and created episodes that revolved around runway shows for Calvin Klein and Anna Sui. “New York Fashion Week was absolutely crazy,” said Mills. “We would run around every day, and then end up at Balthazar”—Manhattan’s biggest celebrity hotspot at the time—“with Cindy [Crawford] and Christina [Aguilera]. It was surreal.”

But though Mills knew what he was witnessing was a special moment in pop culture, he hadn’t considered how the fashion he was documenting would impact the interests and spending habits of non-fashion obsessives. A few years later, he was on the set of Total Request Live: “We had an ‘MTV Style VJ,’ which was a real job, in like 1999, 2000. His name was Coltrane Curtis, and we were on the red carpet filming something. He was wearing these bright pastel colors—pink, peach, what I thought of as ‘My Little Pony’ colors. This was pre-Pharrell, you know? This was not cool yet. But sure enough, a few weeks later, dudes in New York City are wearing this stuff. And I thought, Oh. That’s us. Millions of kids are going out and buying this now.”

Chicer Than Fiction

Remarkably, 1994 is also the birth year of Friends, the most-watched sitcom of all time. The pilot episode introduced the world to future fashion icon Jennifer Aniston, and the series inaugurated real-world trends like the famous “Rachel” haircut and those tiny little mock turtleneck baby tees we all tried to wear in ninth grade. Through the course of Friends, major plot points for Rachel involved getting—and losing—jobs at Bloomingdale’s, Ralph Lauren, Gucci, and Louis Vuitton. “We were seeing fashion used as a goal, not just for real people, but, like, imaginary people!” Ambrose exclaims. “It was exciting, but also, a little weird.”

It was a change from the past, when TV writers invented fictional labels for their equally fictional characters. In the ‘80s, fake designer labels (like Gordon Gartrell on The Cosby Show) foiled sitcom characters in pursuit of the perfect image; Boulmiche boutique in Beverly Hills was disguised for Pretty Woman’s epic “Big mistake. Big. Huge!” scene. We never learn the designer of Can’t Buy Me Love’s white suede jacket, or the similar one worn by Sloane in Ferris Bueller’s Day Off. And while Molly Ringwald flaunts her fashion cred in both Pretty in Pink andThe Breakfast Club, there are scant designer names in the dialogue.

But as fashion flirted with Hollywood in the 1990s, Hollywood flirted back, using designers and brands to help create more realistic—and in some cases more exciting—plot points. In 1995, Clueless became a surprise blockbuster hit, raking in $88 million and turning rarified brands like “way important designer” Alaïa into household names. (Refreshingly, Clueless also featured Contempo Casuals, the mall staple that’s now name-checked in TikTok videos referencing coveted “rave baby” looks—and that teenagers could actually afford with their babysitting money.) 

In 1998, Dawson’s Creek vixen Jen Lindley (Michelle Williams) was demonstrating her bad-girl cred by shoplifting Urban Decay makeup from a local Capeside boutique. In She’s All That, mean girl Taylor Vaughn flaunts her dominance by loudly bragging about her Richard Tyler prom dress. 10 Things I Hate About You features a now-iconic scene in which Gabrielle Union laments her lack of a Prada backpack. Even Seinfeld, a noted pioneer of #normcore, had episodes devoted to real fashion brands: In one, Jerry’s stand-up comedy nemesis taunts him with a “free” Armani suit in exchange for his friendship; in another, George’s puffy Goretex jacket is a literal punchline.

“Putting fashion in movies like Clueless really started changing everything,” says Jeanne Chavez, the co-founder of Hard Candy, which also launched in 1994 and saw its pastel nail polishes explode in popularity, thanks to an early appearance on Cher Horowitz herself, Alicia Silverstone. “She wore us on Letterman and, immediately, the demand grew. But back then, there was no such thing as an ‘influencer agent,’ or whatever… celebrities discovered our nail polishes alongside regular girls because they all shopped at Fred Segal in Los Angeles,” where Chavez’s co-founder, Dineh Mohajer, had a part-time job and slipped bottles of her nascent nail lacquers to customers on the side. 

“The best part was we had this Hard Candy office in Beverly Hills, because all we cared about was having a Beverly Hills zip code on our company,” Chavez laughs, citing the influence of Clueless and 90210 on that era’s fashion branding. “But we didn’t have any full time employees. Instead, this Beverly Hills office was filled with literally college kids answering our 1-800 number. We didn’t accept credit cards, so you had to send us a check. And sometimes, high school girls would just show up at our office and ask to pick up their nail polish. They were curious about what we all looked like, what we wore. They thought maybe we were the Clueless girls, but the real ones.”

Thanks to their pop culture exposure, Chavez struck a deal with Nordstrom to sell Hard Candy, then parlayed that distribution to London stores like Harvey Nicols and Harrods. “I think it showed these major department stores that you couldn’t ignore teenage girls, and teenage girls loved the style in TV and movies. So you couldn’t ignore that either.”

Once Sex and the City debuted on HBO in 1998, Carrie Bradshaw and her cynically chic friends were entering a pop culture cycle that cared as much about what a character was wearing as who she was dating. There was only one of Aiden or Mr. Big, after all, and anyway, they were fictional. The Manolo Blahniks on Carrie’s feet and the Chanel flowers pinned to her vintage blazers, however? Those were very, very real, and their sales numbers climbed every time Sarah Jessica Parker took a televised stroll down Perry Street.

Designer as Star

The year after Silverstone giggled about her Hard Candy nail polish on The Late Show with David Letterman, Rowley appeared on the same program to discuss her own designs. “They were doing a real push to explore things other than TV and movies,” says Rowley, whose episode also included actor David Schwimmer, pop star Michael Bolton, and opera tenor Luciano Pavarotti. “They understood that fashion was becoming part of entertainment, you know?”

With a go-with-the-flow attitude and an easy warmth, Rowley became a kind of chat show VIP, appearing on Rosie O’Donnell, Good Morning America, Donnie & Marie, the Jane Pauley Show, and even The Oprah Winfrey Show to spread the gospel of cool, fun American fashion throughout the ‘90s. Soon, the celebrities she met in the green rooms became her customers. “I was really lucky, because I met a lot of people. The cast of SNL, actors who have shows coming up, they just wanted to wear something great, and they weren’t running around with a pack of stylists or agents yet. It was just easy to team up.” 

Rowley’s front rows were soon packed with rising stars like Julianne Moore and Scarlett Johansson. Meanwhile, her own celebrity image was starting to form. “I remember a woman on the subway telling me, ‘Oh, you look a lot like Cynthia Rowley. But she’s a big designer—she would never ride the subway!’ I almost died laughing.”

Bloch recalls an even more extreme moment at a Destiny’s Child concert in Chicago. “It was Boys 2 Men, and Destiny’s Child and Christina Aguilera were opening. This was late ‘90s. I was with a friend who was a parole officer—didn’t know anything about fashion. But suddenly, this group of guys saw me, and they were like, ‘Oh my god, are you Phillip Bloch? Are you the man who dresses Halle Berry?!’ I was mobbed. It was crazy, and it was a pretty good taste of what my clients were going through when they encountered paparazzi. I never thought that would happen through fashion, though.”

If you were a fashion geek or a film snob in the ‘90s, you likely saw Unzipped, the black-and-white documentary that followed Mizrahi as he built his epic “Nanook of the North” collection, with appearances from Kate Moss, Naomi Campbell, and future House of Style host Shalom Harlow. But by the early 2000s, fashion designers were no longer occasional guest stars—they were the headliners. Mizrahi himself had a talk show, called Isaac, that featured A-list talent like Keira Knightley and Selma Blair; it ran for 15 episodes. Kimora Lee Simmons was a beloved America’s Top Model judge who used her Babyphat fashion show as the final crucible for wide-eyed contestants. 

And as fashion designers were turning into celebrities, celebrities were turning into fashion designers. In 2004, Missy Elliott partnered with Adidas in what’s now considered a groundbreaking deal for hip hop artists and sneaker brands. “She was a woman, she was a rapper, and she was telling fashion executives what would help them grow their brand,” Ambrose recalls. “It was really an epic moment.” Then in 2005 at New York Fashion Week, Jennifer Lopez became the first star with her own runway show; it was for her streetwear label Sweetface, and came with an MTV documentary special, “Beyond the Runway.” That same year, Beyonce and Tina Knowles launched a ready-to-wear label called The House of Deréon with an appearance on Oprah, and Jessica Simpson began making the affordable high heels that would help her generate billions of dollars in revenue.

The cross-pollination of style and fame proved transformative for some in the limelight. In 2004, just three years after the Spice Girls disbanded, Victoria Beckham created a denim range for Rock & Republic jeans called VB rocks. The experience would help set the foundation for her fashion and beauty empire today. Likewise, Ashley and Mary-Kate Olsen began their careers as sitcom babies on Full House, but pivoted full-time to fashion as adults. Today, their brand, The Row, is considered an apex of “quiet luxury,” with awards from the Council of American Fashion Designers (CFDA) and a roster of A-list retailers including Bergdorf Goodman and Net-a-Porter. Sarah Jessica Parker’s SJP shoe line and country star Miranda Lambert’s collection of cowboy boots have equally impressive retail footprints, while beauty ranges like Fenty (by Rihanna), Rhode (by Hailey Bieber), and Rare (by Selena Gomez) now out-sell major makeup companies. But of course, not every fashion-and-celebrity partnership results in accolades or piles of cash. We’re still wondering, for example, what happened to Justin Timberlake’s fashion label William Rast or the singular season of Lindsay Lohan’s takeover for the Parisian couture house Ungaro. (Have an archive sale, Lindsay!)

“It’s like there’s no wall at all anymore,” says Bloch. He has his own cashmere collection, Omniscient Things, made with sustainable wool. (Brad Pitt has one too, called God’s True Cashmere.) “You can be in movies. You can make clothes. That’s all amazing. But will it ever be as fun as it was in the ‘90s, when people weren’t getting paid to wear stuff, they just thought it was cool? And nobody needed you to tag them on Instagram?”

So those golden fashion years of spontaneous, joyful glamor with a side of Chateau Marmont fries are over. But the actual clothes that made ‘90s Hollywood such an iconic time? “Oh gosh,” laughs Ambrose. “You can buy that stuff for like $50 on eBay. It’s all over TikTok. Everyone still wants to dress like a famous person in the ‘90s. So I guess, you know, we did our job.”