It was time for her to officially cross over.
CHAPTER SIX: TOMMY GIRL
When I see Tommy Hilfiger, I think of Aaliyah.
—H.E.R., i-D magazine, 2020
One in a Million kicked off a new iteration of Aaliyah that was rooted in experimentation. Sonically, it was a no-brainer that working with both Timbaland and Missy opened up a whole new world of sound and style, but it was Aaliyah’s stylist, Derek Lee, who provided her aesthetic to match that music. Her makeup artist, the late Eric Ferrell, was at the helm of keeping her makeup consistent—as he worked with Aaliyah from the beginning during her earliest “tomboy” years. He even maintained her signature thick eyebrows that later remained en vogue for women everywhere. At the heart of all of their curation, however, it was still Aaliyah who shone through. Gone were the days of simply acquiescing to a mentor and using her strong acting chops to be his puppet. No, now we were slowly learning about who the real Aaliyah was, and she exuded that on every song and in every outfit. It came as no surprise that the ingenue with washboard abs was destined for modeling. What was waiting to be discovered, however, was how one designer utilized Aaliyah’s flawless figure as his canvas, as well as her personality and vibe within his clothes to set the visual standard for his clothing line to follow.
His name was Tommy Hilfiger.
Hilfiger cut his teeth in fashion in 1969, when he launched a store called People’s Place with some friends in his hometown of Elmira, New York. The store grew into more locations throughout upstate New York, though they went bankrupt by 1979. In 1985, he started Tommy Hilfiger, his own eponymous line dedicated to “classic, American cool” menswear. By the nineties, Hilfiger was embraced by hip-hop, once the fashion trend “urban preppy” took off. There was also an allure to the Hilfiger designs that spoke to hip-hop beyond the growing rugby shirt and windbreaker trends happening within the culture. Tommy utilized color schemes differently. He paired bold hues with subdued ones. There was rarely a timid earth tone in his designs, though something about bright yellow sewn beside navy blue just popped.
Tommy Hilfiger’s clothing line became something of a hip-hop fashion staple at a time when designer clothes were slowly entering the rap fashion purview, but in an unconventional way. The juxtaposition of street rappers in preppy clothes ran rampant, which offered designers like Hilfiger the opportunity to slide right in and corner a market that was previously uncharted, at least for them.
What was once the uniform for preppy white guys who were into sailing or horseback riding (the names and logos of Nautica and Polo are proof alone of that) traveled over to the other side of the tracks and landed on the backs of drug dealers turned record-label owners and rappers. It was the loudest secret that these clothing designers weren’t pleased with the new “street marketing team” for their clothing lines but loved their deep pockets. After all, the brands each carried significant price points for shirts, jackets, and jeans, yet in the minds of executives there was no guarantee that poor Black kids could play the long game with their clothing and keep their bottom lines healthy for years to come, like their previous audience. And once that audience saw the new adopters of those brands, they may be less likely to sport them. It made sense but didn’t make it any less disturbing.
Hip-hop’s relationship with fashion is pretty extensive. It started in the late 1970s and early 1980s, when the preteen and teenage hip-hop pioneers left their bedrooms and congregated in the parks that split up the South Bronx housing projects for outdoor jams in the summertime and packed roller rinks, clubs, and event halls once the weather chilled. Hip-hop culture was built on fashion. In fact, the documented “birthdate” of hip-hop (August 11, 1973) is celebrated because of a fashion fundraiser. Hip-hop’s founding father Kool Herc deejayed his sister Cindy Campbell’s back-to-school party at 1520 Sedgwick Avenue in the Bronx, where she charged at the door in an effort to pay for her new school clothes.
Crews during the seventies and eighties had matching jackets sewn with their names on them and would often dress in the same outfits when they were onstage performing. Groups like Salt-N-Pepa were twinning in their 8-ball-style leather jackets and spandex pants with bamboo earrings, an eighties staple accessory. The legendary Daniel “Dapper Dan” Day became known as a Fashion Outlaw when the Harlem native took a printing machine and counterfeited overpriced logos of designer fashion houses and plastered them, head to toe, on articles of clothing. That need to be fashionably cutting edge remained a prominent theme in hip-hop after decades of fashion evolution. As the top preppy designers (Ralph Lauren’s Polo, Nautica, and Tommy Hilfiger) were luring in the hip-hop crowd while simultaneously scared of it, rumors started circulating that there was widespread objection to rap artists in their clothes.
Tommy Hilfiger was the first to come under fire, when the designer and his brand were rumored to have expressed a disapproval of people of color wearing his clothing. It was a gradual snowball that had begun to develop when a further rumor stated that Hilfiger allegedly said he wouldn’t have made his clothing “so nice” had he known it would be worn by POC. A boycott campaign had taken off from there, and then another rumor fueled the fire when Hilfiger apparently appeared on Oprah and defended his stance about not wanting POC to wear his clothing. This era predates YouTube or even a sophisticated internet, so really no one was on hand to pull up this fictitious episode or even create a social media post denying those claims. It then traveled through nearly every minority community, where Jewish people and Latinx people alike were told that they were also on the “Do Not Wear” list for Hilfiger. The rumors lingered on for years—over a decade in fact. Hilfiger eventually really went on Oprah in 2007 to address it, though like he told “Godmother of Fashion” Fern Mallis during their interview as part of 92Y’s Fashion Icons series, “Some people may still believe it.”
There was really no merit to the origin of those claims; Tommy Hilfiger hadn’t even appeared on Oprah during the time the rumor originated. The only real damage control was to continue with smart collaborations that not only showed the brand’s diversity but also dismissed any idea that there was a preferential person in his fabrics.
That same year, 1996, Tommy Hilfiger expanded its brand into women’s fashion. By August, Tommy’s women sportswear line landed in four hundred department stores within the United States. The next move was to fully immerse the brand into music, capturing a whole new consumer. There were already a few moments that foreshadowed his entry into the adjacent industry. In 1994, rapper Snoop Dogg landed his first performance on Saturday Night Live and was wearing a red-and-blue-striped Tommy Hilfiger rugby, which many point to as a major pivot for hip-hop fashion. Snoop was dressed for the performance by Tommy’s brother Andy Hilfiger, who was the director of public relations for Tommy Jeans. It was also the shift where Tommy Hilfiger became the go-to uniform for true school rap fans.
Tommy Hilfiger secured his next hip-hop moment, when he custom designed a shiny silver suit for Sean “Puffy” Combs’s performance at the 1997 MTV Video Music Awards. That suit signified what many hip-hop historians refer to as the hard switch—where in a post-Tupac and post-Biggie world hip-hop became diluted by the mainstream—known as the “Shiny Suit Era.”
Hilfiger’s portfolio also included rock, as he dressed the legendary Rolling Stones for their 1997–1998 Bridges to Babylon Tour, after Tommy partied with Mick Jagger in the Caribbean. Everyone from Sheryl Crow to Gwen Stefani and Treach from Naughty by Nature has also worn Tommy Hilfiger in public. The real impetus behind the music came from Andy Hilfiger. Andy would scour the hip New York City nightlife scene in the nineties in search of the next big partnership. Andy loved music and working with musicians, so the partnering really meant something to him. He later even started his own record label.
The ads for Tommy Hilfiger boasted these “coming of age” lineups of young models and actors, where their success was foreshadowed by their placement on these ads. With hip-hop, though, it was less about the ar
tists’ appearance in these campaigns and more about them being dressed in Hilfiger as walking advertisements. The goal was to find someone who could fluidly do both.
Hilfiger added another hip addition to his team, Kidada Jones (the daughter of Quincy Jones and Peggy Lipton), who styled for Hilfiger in the past. In 1997, she still held an unofficial post as both a talent scout and a consultant for the company. “Me and Aaliyah met at a Tommy Hilfiger fashion show that I styled in about ’93,” Jones told The FADER in 2008. “She had really small feet and so did I and she didn’t have shoes for the show, so I remember loaning her my shoes. Then we met again on the Tommy Hilfiger photo shoot when we were both in the ad.” They immediately connected and later became best friends. “Her mom allowed me to be her guardian for a little bit,” Kidada continued. “I was a few years older, so when she went to Europe I was the guardian—which was a complete and total nightmare. I’ll keep it mild, but it was just young fun and maybe I didn’t really understand the boundaries. We got in trouble quite a few times, but she was the funnest friend.” They even had plans one day of launching their own clothing and accessory line called Dolly Pop.
Kidada and Aaliyah reunited professionally in 1997. That was the year Tommy Hilfiger made a game-changing decision to have Aaliyah included in his spring line marketing campaign, at the behest of Andy and Kidada. As always, the talent was handpicked in the hopes that their celebrity would later become a check point in these ads, but with Aaliyah he saw something bigger. Tommy Hilfiger needed Aaliyah.
In the spring of 1997, Tommy Hilfiger launched his “Next Generation Jeans” campaign. The group of young celebrities who were a part of the campaign included a pre–Almost Famous Kate Hudson, producer Mark Ronson, Kidada Jones, and of course Aaliyah.
By this point, Aaliyah was a full-fledged music star. One in a Million was out for nearly a year, so she had not only proven there was no sophomore curse, but she was even bigger than before. And again, a growing tastemaker in the fashion world. So with her natural beauty and body that could wear any outfit, modeling was also an inevitable foray. She was a longtime Tommy Hilfiger fan and wore the clothes on her own, but Atlantic Records reached out to Hilfiger gauging their interest in working with Aaliyah, and Andy readily put her in their ads. Aaliyah wasn’t the tallest—she stood at five-seven—but with washboard abs and a dancer’s physique, she had the luxury of being able to wear baggy clothes and tight clothes and still look amazing in both. She was undoubtedly the star of the campaign, but the costar was definitely that memorable outfit she was in.
Many will clearly remember her notorious Tommy Hilfiger uniform. Aaliyah wore a tube top with the infamous Tommy flag of half-red, half-white, and a navy blue trimming that partially framed the logo. Her bottom half included loose denim with one red and white leg and one navy blue leg. “Tommy” is stitched from hip to ankle on one pant leg, “Hilfiger” on the other. They’re slung low enough to reveal the thick waistband of Tommy Hilfiger boxer shorts that she’s wearing underneath. A unisex Tommy belt completes the outfit. Her campaign video was shot by Mark Ronson, where Aaliyah is gracefully dancing as she voices over the video in her lightly delicate tone, discussing her parents and where she gets her traits from. It was a sweet clip where she was able to both honor her family and show while also showing yet again why she was so incomprehensibly magical. There was also this air of self-love, since she’s answering the hypothetical question of Why are you so fly? with It’s in my genes/jeans.
The print ads became legendary; Aaliyah has her hands up and is tilting to the side, angled beside Ronson, who was perched behind two turntables. Another ad showed Aaliyah shyly standing behind the turntables herself, with one headphone cupped on her ear and propped by her shoulder, as she attempts to scratch a record and push the crossfader. Once the ads appeared in magazines, they sold out of all twenty-four hundred of the limited-run jeans and immediately requested five thousand more from the Tommy Jeans factory. “After we started working with Aaliyah, we put a lot of that stuff [she wore] into the line,” Andy Hilfiger told Complex in 2016. “Tommy Girl was [previously] very preppy; it had a lot of plaids and was very schoolgirl. But then we added this whole Aaliyah look to it, which really gave it some new legs.”
By the fall, Tommy Hilfiger handpicked Aaliyah as the face of his fall 1997 campaign. His entire women’s line that year was designed with Aaliyah in mind. Before Aaliyah even endorsed a stitch of the designer’s thread, both Tommy and Andy knew that she was setting trends with her style. The way Aaliyah combined men’s clothing with women’s, the way her clothes fit her, the way she carried herself in them… it was transformative. So the Hilfiger brothers used their clothing to reflect her existing swagger—a combination of men’s fits with women’s, compliments of their Tommy Jeans line.
Aaliyah’s look became iconic in almost record time, and the impact has lasted for decades.
The ads appeared not only in magazines like Vibe but also in the metal doors inside of high school lockers, on the walls of fans’ bedrooms, at the front of fashion marketing boardrooms, and glued to the cardboard of personal (and professional) vision and inspiration boards. Further, while Tommy Hilfiger did a strategically impressive job of having Black men openly support his brand, he didn’t have Black women. Aaliyah became a reference point for young girls who never saw themselves in a Tommy Hilfiger ad, especially Black- and Brown-skinned ones. If they couldn’t see themselves in an ad, how could they possibly see themselves in his clothing? What Aaliyah accomplished was she bridged the gap between Hilfiger’s ultra-preppy reputation and his desire to reach the cool kids, the inspirers, and yes, the “urban” crowd.
Above all, it showed Aaliyah truly as a growing style icon. Aaliyah wasn’t dressed in Tommy Hilfiger, Tommy Hilfiger was dressed in Aaliyah, and that became clear with this one casually fly outfit. It was more than Aaliyah bearing her abs and no sunglasses, revealing the true essence of her beauty. She looked comfortable in her skin. For so long she was hidden by the styling bells and whistles. Sure, they looked wonderful on her, but this clean look showed that underneath it all, Aaliyah was still very much a star. This was also one of the first times a female R&B artist was a model for a designer fashion brand and received such a massive endorsement. Aaliyah broke down doors previously shut for women and in doing so created a legendary moment in fashion history that rendered her untouchable.
“What Aaliyah really did was show this style, the sexy but sporty-chic style. She brought this swagger, this sexiness. It was just incredible,” Andy Hilfiger told Complex. “I give Kidada a lot of credit, because she had such a vision. She and Aaliyah were on the same page. And Aaliyah loved Kidada and would listen to anything she said.”
It’s the reason why twenty-three years later during an episode of ABC’s prime-time comedy Grown-ish, the character Zoey (played by Yara Shahidi) wears Aaliyah’s exact Tommy Hilfiger outfit for a costume party on the show’s 2020 season finale. When R&B singer/songwriter H.E.R. was asked that same year by Tommy Hilfiger to design a capsule collection, she told i-D that when she recalls her memories of Tommy Hilfiger as a child “I always think of Aaliyah!” When recording artist Lolo Zouaï secured her own brand ambassador deal with Tommy Hilfiger, Aaliyah was also at the front of her mind. “She was bringing a style to women’s fashion that was also masculine,” Zouaï says. “ ‘I’m working with Tommy Jeans, because to me, I was like, “ ‘Okay if someone as iconic as Aaliyah wore this then it’s like why not continue that legacy?’ ” Zouaï has a line on her song “Blue,” off her 2019 critically acclaimed album High Highs to Low Lows, that even references Aaliyah. “I feel like her voice and her style and everything was just so one of a kind,” she continues. “There are not that many artists that come around in the world that are like her, that completely change the music industry. She definitely did that.”
And that’s what Aaliyah did: she was the person who for years to come remained the face of a brand that seemingly struggled to understand wh
at their perfect face looked like. While there’s no real perfect paragon who could speak to every person in one outfit, Aaliyah came damn close. Even outside of Tommy Hilfiger, Aaliyah represented something: the unapologetic tomboy who didn’t compromise comfort for cutesiness. Karl Kani even circled back in 2020 to re-create her look on the cover of Age Ain’t Nothing but a Number in his line’s black hoodie, using rapper Coi Leray as the muse. Hip-hop legacy clothing brand Cross Colours also released a capsule collection in 2020, featuring designs with Aaliyah’s image on everything from shirts to slides. While her image is readily painted and stitched across clothing nowadays, worn by stars like Halsey and everyday fans alike, it really comes down to how Aaliyah wore her clothes, which in turn changed generations’ perceptions of what qualified as womenswear. Aaliyah proved that women could wear anything they wanted.
Grammy-nominated artist Rapsody composed an ode to Aaliyah’s tomboy style, with her song aptly titled “Aaliyah,” where she rhymes, “When Aaliyah was alive, it was cool to be a tomboy. Tommy boy fly.” The song was the centerpiece of her 2019 critically acclaimed album, Eve, where each track is titled after a groundbreaking Black woman. The song is an ode to being that proud tomboy, something that both Aaliyah and Rapsody embody. “That was the very first song I did [for Eve],” Rapsody explains. “I had been wanting to do a record about being a tomboy. And I have written it over and over again, but it never was the right time. I could never express it the way I wanted to.” When she finally did and thought of a title for the song, only one name came to mind. “And it was at that moment, I named it ‘Aaliyah,’ ” Rapsody continues. “I was like, I should do an album and just name songs after women. So she was the first one I did. I wanted people to know that Aaliyah had a crazy big influence on me and she taught me how to be sexy and be myself at the same time.”
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