Twenty-two years is not a long life, but it was long enough for Aaliyah to make an indelible impact on music, culture, and, perhaps most recognizable in everyday life, fashion. This week marks 20 years since the singer’s tragic death in a plane crash, yet her sartorial influence is palpable as ever.
A Brooklyn native born Aaliyah Dana Haughton in 1979, the singer was raised in Detroit and quickly rose to prominence following the release of her debut album, Age Ain’t Nothing but a Number, in 1994. Her sound was unlike anything the world had ever heard—smooth, pitch-perfect vocals layered over futuristic hip-hop and R&B beats—and was matched with an innate talent for dance, incorporated into her cinematic music videos. The titular song of Aaliyah’s sophomore release, One in a Million, is widely recognized as one of the greatest hits of all time, and since the debut of her final studio album, Aaliyah, it’s estimated that she’s sold between 24 and 32 million albums worldwide. Expanding the range of her career, she started to establish herself as an actress, starring alongside Jet Li in the 2000 action film Romeo Must Die and playing the lead in Queen of the Damned, released posthumously in 2002. Aaliyah often garnered as much attention and praise for her style as she did her work. Her wardrobe of oversized silhouettes, bra tops, bandanas, and tinted sunglasses both elevated and redefined what’s oft considered a “tomboy” look—one that’s still referenced today.
“I was watching MTV when the ‘Back & Forth’ video premiered, so I have that memory of feeling like it was the first day that anyone experienced Aaliyah,” author and journalist Kathy Iandoli, whose biography, Baby Girl: Better Known as Aaliyah, was released earlier this month, says. “I remember she was wearing the bandana, and she had on the shades; and then, she had on the layered tops with her midriff [exposed] and the baggy jeans and the big belt. I was just like, ‘This is the coolest person to ever walk planet.’”
Like Iandoli, stylist Derek Lee also remembers seeing Aaliyah’s “Back & Forth” video and marveling at her style and demeanor. “Her style was right up my alley, so that’s why she stood out to me,” Lee tells BAZAAR.com. “I thought she was dope.” Two years later, in 1996, Lee was traveling from Los Angeles to New York City for work when his agent got a call from Aaliyah’s record label asking if he was available to show her some pieces for an upcoming shoot before he left; the magazine was attempting to put her in dresses that simply weren’t her. “I showed her some stuff, and she loved it,” he says. “I got on my plane, [and] by the time I landed [in NYC], my agent was like, ‘You have to get right back on a plane tomorrow morning, because she wants you to do her ‘One in a Million’ video.”
For the video, Lee styled Aaliyah in leather pieces he found at sex shops on Christopher Street (the only clothing stores that were still open when he got in late at night) and a racing suit that was shipped same-day air from an NYC showroom the next morning; it arrived on set in L.A. a few hours after Lee did. From that day on, the two became close friends, collaborating on dozens of now-famous looks. “I met her one day, the next day I was her stylist,” Lee says.
While pleated skirts and slinky slipdresses were being sent down runways and featured in the pages of fashion magazines at the time, Aaliyah was seamlessly blending the streetwear trends born in urban communities with her own sense of style. “She added her touches to everything,” Lee says, “especially with the bandanas; that was all her. [When] it was time for her to elevate, we went towards Chanel scarves and Fendi scarves—stuff like that.” Lee notes that Aaliyah didn’t invent the masculine-meets-feminine aesthetic, “but she perfected it,” he says. “I saw it in other people’s music videos, and I definitely saw it in the streets.”
Aaliyah’s career coincided with the emergence of brands such as Baby Phat, Enyce, Rocawear and Sean John—all birthed from the influential hip-hop and R&B circles she was within. “My favorite Aaliyah look is her in the ‘Crush on You’ video,” Iandoli says, “where she’s wearing the big Tommy [Hilfiger] jacket, and she has the shades on.” She adds, laughing, “I bought that coat—of course, it looked nothing like that on me.”
Tommy Hilfiger tapped Aaliyah for its Tommy Jeans ad campaign in 1996, which marked the brand’s foray into womenswear. Aaliyah was the first R&B singer cast in a campaign of that caliber, and the bandeau top, baggy jeans, and exposed boxer briefs she wore in the ad became instantly iconic. Two years later, Destiny’s Child wore various iterations of the look alongside Hilfiger at a Macy’s event in New York City, and in recent years, both Zendaya and Yara Shahidi have replicated it in homage to Aaliyah.
Though much of her wardrobe was casual—and she wore a lot of streetwear pieces that Lee customized for her—at times, Aaliyah gravitated toward luxury labels. Armani was a favorite, as was Dolce & Gabbana, the house behind the mesh diamante bra she and Lee paired with a matching choker and low-slung belt over leather pants for the “Try Again” video in 2000. That same year, she wore what’s arguably her most celebrated red-carpet look to the MTV Video Music Awards: a black-and-yellow zebra-print Roberto Cavalli dress from the label’s fall 2000 collection.
Lee was on vacation in Europe when he got a call from his agent saying that Aaliyah needed to be dressed for the event. Rather than cut his trip short, Lee went to the Roberto Cavalli store in Milan, selected a few pieces that he liked, and called the Roberto Cavalli boutique in New York City to have them pull those same looks and set them aside for his assistant to pick up. “I thought the yellow was perfect for her,” he says. “It stood out more than any of the other colors.” Though there were multiple dresses for her to choose from, Aaliyah immediately gravitated toward Lee’s favorite and ended up wearing it. Like many of her style choices, that wasn’t the last time it was seen the world over and met with fanfare. Model Paloma Elsesser had stylist Eric McNeal track the dress down for a wedding she attended earlier this year, and quickly confirmed that the sartorial nod to Aaliyah was intentional.
True to its cyclical nature, fashion is currently revisiting the dominant trends of the late ’90s and early 2000s—some popularized by Aaliyah—both on and off the runway. Shayne Oliver’s Hood by Air and Helmut Lang collections, Alexander Wang—particularly with his T line—and, unsurprisingly, Tommy Hilfiger collaborations with Gigi Hadid and Lewis Hamilton have all reflected her influence. Today, baggy pants and a crop top is the off-duty look of choice for Hailey Bieber, Bella Hadid, and others. Similarly, tinted sunglasses and bra tops that crisscross at the midriff are once again wildly popular. Had she lived longer, it’s likely that Aaliyah’s own designs would be trending as well. At the time of her death, she was working on a Japanese-inspired clothing line coined Dolly Pop with her best friend, Kidada Jones.
It may not be possible to articulate the full breadth of Aaliyah’s impact on fashion, but her legacy has no doubt transcended time, resonating with multiple generations across the globe. Her style especially resonated with girls and women who, like her, did not want to be confined to clothes that were short, tight, and considered traditionally feminine. Aaliyah gave them license to dress in exaggerated proportions, thus allowing them to be themselves more freely and confidently.
“Growing up as a Brown, South Asian girl from the late ’80s to early ’90s, I was such a tomboy,” Sandy, who lives in the United Kingdom and prefers to go by her first name, tells BAZAAR. “My mother tried to make me wear dresses, and I just simply refused. Aaliyah had those tomboy tendencies, too, and it gave me comfort knowing I wasn’t alone as a girl growing up.” In 2013, Sandy founded the fan site Aaliyah Archives, which has since grown to include an Instagram account with 18.6 thousand followers. Another Instagram account, @aaliyahwore, was created earlier this month by Philip Wallin of Västerås, Sweden, and focuses solely on Aaliyah’s style. “I loved how she was not afraid to incorporate things that were different or quirky in her looks,” Wallin says, “like her signature Yohji Yamamoto sunglasses.”
This interest in her is no surprise to those who knew her well. “She was so original and authentic,” Lee says, “and people gravitate towards that. It never goes out of style.”