When you have the conversation of women in streetwear culture, you have to pay homage to the iconic women who took menswear and unisex clothing into their own hands and made it into a lifestyle that continues to carry on through generations. MC Lyte, Missy Elliot, Queen Latifah, Da Brat, and TLC are a few of the icons who paved their own lanes in streetwear through the ‘80s and ‘90s and will always have a place in this conversation. But when you speak about mixing streetwear, femininity and sex appeal to someone’s personality and lifestyle, the only one during this time period who brought it all together so effortlessly was Aaliyah. 

Aaliyah Dana Haughton came on the scene when the culture and fashion industry was at its peak in the ‘90s. It was also during this time period where the reign of the supermodel was at a high as well. For Aaliyah, the tomboy-style, baggy streetwear clothing wasn’t a trend, it was directly aligned with her personality and identity, and elevated as she grew older with her stylist, Derek Lee. She didn’t have to put on an outfit with the aspiration of making a scene or to be talked about. Some of her most iconic outfits were just that because it was the way she carried herself while wearing them. In an interview with MTV News in 1994, Aaliyah gave a statement about her style saying, “I dress in my baggy clothes everyday. I’m a laid back person, which is what I betray on the camera. I’m laid back, I’m mellow, I like the jazzy music, so it’s not much of a difference because it really is how I am.” She carried that mindset from the time she stepped on the scene, and through her legacy 21 years after her untimely death. This is why she is the epitome of what we know as the streetwear girl.

Our introduction to Aaliyah’s style was with her debut album, Age Ain’t Nothing But a Number. She called her style “street and sweet”, which was made of baggy tops and bottoms, oversized sunglasses, skull caps, and of course, her sneakers. She understood that image went hand in hand with her music, as well as staying in the know of what the current fashion trends were to make them into her own. However, as she got closer to debuting her second album, One In A Million, she knew she needed to elevate style along with her music. In came her stylist, Derek Lee. “Her whole thing was, ‘I’m a star, but I need to be a regular girl, too,’” says Lee in an interview with Complex Magazine. “So everything needed to be a little bit relatable because that’s who she was. We made things attainable on purpose.” 

When Derek Lee began working with Aaliyah as a part of her glam squad in 1996, he immediately felt the synergy between them was meant to be. His first styling job for her was for the “One In A Million” video where he only had a few hours to get pieces for the shoot. He headed to New York’s West Village because the only “clothing” stores that were open late at night were sex shops. One of the pieces he found was the all-black motorcycle outfit that we see at the beginning of the video. From this point, Derek Lee and Aaliyah would go on to be one of the most iconic duos in fashion.

Derek Lee’s styling career began with Essence Magazine, which gave him a different perspective on how fashion looked and worked. He saw the clothes and the brands that were not made for African American culture and made it his duty to flip it in a way it became for us. He took what was off of the runways and made it into streetwear. Little did he know, this was the foundation of the work he would do with Aaliyah later on. Going into 1996 and 1997, Aaliyah’s music was noticeably transforming from young girl to elegant young woman, and her style elevated as well. Her baggy jeans and boxers were updated into two-piece sets with an open jacket and a bralette, all-leather outfits, jumpsuits, and an introduction to more luxury pieces. This time period also began her brand partnership with Tommy Hilfiger where she became the inspiration for the women’s line. The clothes were still baggy, but she made the outfits into her own by mixing different pieces together with accessories and experimenting with makeup. Her brand partnership with Tommy Hilfiger gave Aaliyah some of her most iconic outfit moments and is still an inspiration to the modern-day streetwear girl we see today.

As Aaliyah entered her twenties going into the 2000s, her style elevated once again showing more of her sex appeal. During the Oscars of 1998, she was pictured in a sleek, off-the-rack, Versace dress. This was a special moment because this was only one of the few times the world had ever seen her in a dress. Still, Lee kept it all about her by not having the wardrobe outshine her or make a scene. From that point, we would see more subtle but sexy moments from Aaliyah’s style such as the $4000 Gucci thong swimsuit in the “Are You That Somebody” video, the snake-skinned outfit in “We Need a Resolution”, and the infamous Diamond-encrusted bralette and choker moment in the “Try Again” video. The fashion industry and other celebrities were taking notice of Aaliyah’s style so much that Derek Lee would receive phone calls asking for “Aaliyah’s look”, which he of course declined. Lee took a lot of time with Aaliyah to keep her look aligned to who she was as she got older. Before her untimely passing, they were beginning to speak more about where they wanted to take her style next as Aaliyah gained interest in Japanese-inspired fashion and liked the idea of looking futuristic. We saw some of this in her music video for “More Than A Woman” where she wore a custom-made Chanel jumpsuit created by Dapper Dan. “Aaliyah looked so good in a catsuit and we wanted it to be designer,” says Lee in an interview with Nylon. “[Dapper Dan] took the idea and he ran with it. It’s pretty amazing.”

As we continue to celebrate Baby Girl’s life 21 years after her passing, there’s not a doubt that her legacy in fashion will continue to live on. She set the tone at a young age of what it meant to be true to yourself and let your image align with who you were on and off the camera. She was the beginning of what we know and love in streetwear because of the way she made it her own, and created the perfect mix of tomboy and sexy. Her style will always be referenced because of how relatable and organic it was. So, whenever you speak about women in the streetwear space and who started it all, Aaliyah will always be mentioned because she was the epitome of what the streetwear girl was and is to this day.

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