How Aaliyah’s Tomboy Style Left An Imprint On Fashion

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Aaliyah’s style, which perfectly blended masculinity and femininity, has left an irrefutable impact on fashion.

The ‘90s were pivotal to the evolution of streetwear by the way of hip-hop, with trends like Kangol hats, track suits, Starter jackets and baggy pants being woven into the genre’s cultural makeup. Rap artists of the ‘80s like Run DMC and Big Daddy Kane, as well backward clothes wearing ‘90s duo Kriss Kross were looked to as trendsetters, donning iconic looks that would become a part of hip-hop’s fashion history. But with the emergence of female artists like TLC, DaBrat and Aaliyah, the presence of tomboy fashion assumed a bigger role in hip-hop’s fabrication.

In 1994, Aaliyah arrived on the music scene with her distinct velvety smooth vocals and boyish style in tow, attributes that became iconic during her short career. The songstress frequently wore oversized shirts, baggy pants and dark shades, a look crafted at the hands of her then-mentor and producer, R. Kelly. The singer and alleged sexual abuser insisted upon the look, and has been stated by prosecution that he preferred women he was sexually involved with to wear baggy clothes when other men were present. Unfortunately, while we will never hear Aaliyah’s experiences recounted, we are left with her quintessential style that simply can’t be ignored.

The Brooklyn-born, Detroit-raised singer’s debut album, Age Ain’t Nothing But A Number, marked the beginning of an era, with her quickly rising to prominence following its release. The 13-track album translated the then 15-year-old Aaliyah’s feelings of being young and navigating unrequited love over hip-hop infused beats and sweet ballads. Her ethereal vocals reprised the teenage girl's perspective in R&B and, combined with her mysterious tomboy aesthetic, she simultaneously garnered attention and fed the curiosity of her new audience. On the album's front and back cover, Aaliyah is photographed wearing an oversized black Karl Kani hoodie, a leather jacket, a black beanie, and blacked out sunglasses. But it's only the back cover that reveals the budding singer's eyes, the sunglasses just low enough to see her soft eyes, a slight contrast from the hardness of her look. While Aaliyah’s introduction to the world was one rooted in obscurity, it was stamped with individuality and fluidity.

"I dress in my baggy clothes everyday and I am a laidback person, which is what I portray on the camera," Aaliyah said in a 1994 interview with MTV. "I'm laidback, I'm mellow, kind of jazzy — I like the jazzy music. So, it's not really much of a difference which is probably why it's so easy, because it really is how I am."

Aaliyah owned her look entirely, often leaning into an androgynous and fluid space at a time where the parameters of masculinity and femininity were much more confined. The “Back and Forth” singer's wardrobe favored loose-fitting jerseys and jackets, roomy pants, crop tops, bandanas, undone belts, visible boxer briefs, and locs (dark-tinted shades influenced by Hispanic culture in Los Angeles). Some of her most impactful looks were disheveled yet polished, and put Aaliyah’s authenticity front and center as she effortlessly donned the outsized garments.

With the release of Aaliyah’s sophomore album One In A Million, there was a noticeable shift in the way she dressed. The evolution of her style still maintained her boyish influence but with more feminine touches. She began to experiment with slimmer silhouettes while still holding onto the baggy look she loved. She also incorporated bra tops that wrapped around her torso, and lots of leather — a true fusion of '90s hip-hop style and futuristic proportions. This era would also serve as an exploration of beauty for the singer: from the sweeping deep-parted bang that upheld her uncanny appearance even when she didn’t wear her infamous shades to her adoption of full makeup looks (previously opting for a fresh baby face). With the expansion of her style to a more femme tomboy aesthetic, Aaliyah asserted herself in conversations of what sexy was and could be, separating herself from other female acts in her class who opted for more form-fitting and dollish looks.

This is evident in the music video for the album's beloved title track, as Aaliyah’s blend of sexual assertiveness and male influenced aesthetic marry fluently. At the beginning of the video, she lays on the hood of a car wearing a full black leather look: an open front crop vest and crop shirt with wraparound arm detailing paired with slim fitting pants.  The outfit is a peak into Aaliyah's ever evolving style that reprised itself for the latter of her career. Although the artist was more femme presenting during this span of time, it didn’t forgo the edge and obscurity that had been ingrained in her image from the start. The wardrobing that followed in the video restated the baggier silhouettes, pairing them with pieces that delved further into Aaliyah’s sensuality.

In 1996, lifestyle brand Tommy Hilfigerstruck a deal with Aaliyah, a partnership that proved to be a true extension of the acclaimed singer’s solidified aesthetic. Two of her most iconic looks were birthed from the alliance: an encapsulating yellow tracksuit lined with a foil-like material and layered with a complementing bra top, as well as the heavily branded red, white and blue tube top paired with baggy color-blocked jeans. The essence of Aaliyah became a beeline for Tommy Hilfiger’s entry and mainstay in streetwear, with her inspiration being archived into the brand’s foundation.

"I've always bought Hilfiger ever since he first came out because I always felt that it was me," she said in a 1997 interview with E! News. "My image is the baggy pants, the tube tops, and I've always loved Tommy. So, it's great for me to model his clothes because I really feel comfortable in it."

In subsequent years, the late singer’s indelible impact has re-emerged through the lens of artists like H.E.R and Billie Eilish, who have adapted Aaliyah’s way of maintaining anonymity with dark eyewear and bulky clothing choices. Rapsody has also shared how Aaliyah's style impacted her, even dedicating a song to singer on her latest album, Eve. 

"'Aaliyah' was the first song that I did for this album and in thinking about that song, I am tomboy feminine. I am tomboy in how I define sexy," Rapsody said in an interview with Hypebeast. "Because when people say sexy we kind of box it in sometimes like, 'Oh, you gotta show your body, your curves.' But sexy to me is just being yourself." Also taking cues from Aaliyah’s legacy is Normani, who channelled the legendary singer in the video for her new single "Wild Side." The seductive track pays homage to Aaliyah in more ways than one, sampling the sultry ballad “One In A Million" while mirroring choreography and wardrobe from the many eras of the iconic artist. Through the years, many have replicated Aaliyah’s enigmatic looks down to a tee. But most recently, playwright Jeremy O. Harris made a statement at the 2021 Met Gala, sporting a rendition of the aforementioned yellow Tommy Hilfilger tracksuit in the form of a larger-than life coat. Beyond her musical influence, Aaliyah’s ability to walk the line of masculinity and femininity, and also perfectly blend the two when she wanted, has left an irrefutable impact on fashion.

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Mikeisha Daché Vaughn is a culture writer based in Columbus, Ohio. Her work is mostly culture-based, but the ways in which her writing intersects with music and fashion is her Achilles heel. She has also written for Complex, Essence, and Teen Vogue, among others.