Aaliyah's late-1990s and 2000-era look is one of the most referenced style moments in R&B history, and at The Closet Inc. it's a moment we think about often — because the silhouettes she made iconic are the silhouettes we still put on the counter every day.
The Try Again era: bra tops, baggy pants, and a single outfit that did it all
The video for Try Again (2000) is built around one look. In an interview with Nylon, Aaliyah's former stylist Derek Lee said he knew it was going to be a dance video and that she was going to "wear one outfit for the entire thing." The look: a crystal bra top with a matching choker by Dolce & Gabbana, paired with the baggy low-rise pants that had become a signature of Aaliyah's red-carpet and music-video appearances. Lee told Nylon he saw an ad for the top in Vogue, and that it was still "for something that was coming out for pre-order." He chose the plain-crystal version because it came with a matching belt and choker, and added extra rows of rhinestones so Aaliyah felt more comfortable on set. The result was the look that ran for the full four minutes of the video — and the look that defined the baggy-pants-and-sports-bra silhouette going into the 2000s.
The Tommy Hilfiger co-sign: when R&B style met American prep
In 1997, Aaliyah became a spokesperson for the Tommy Hilfiger Corporation. The campaign put her at the centre of the red-white-and-blue Tommy era — the baggy varsity jackets, the wide-leg Tommy jeans, the cropped logo pieces — and made her one of the most visible faces of the brand's late-90s push. According to a Tommy Hilfiger Corporation history, the company sold more than 2,400 pairs of the red, white and blue baggy jeans she wore in the advertisements. It was a verified brand co-sign at the highest level, and it cemented the connection between R&B performance style and the baggy-Tommy silhouette that defined the rest of the decade.
The footwear rotation: Timbs, Air Force 1s, and Air Jordans
The footwear associated with Aaliyah's late-90s and 2000-era style was a rotation rather than a single signature shoe — and that rotation is one we still see at The Closet Inc. every week. The Timberland 6-inch Premium boot, the Nike Air Force 1 '07 Triple White, and the Air Jordan 3 Retro are the three silhouettes most often credited with anchoring the look. They aren't all worn at the same time — the Timbs go with the baggy Tommy jeans, the AF1 Triple White goes with the sports-bra-and-baggy-pants stage looks, and the Air Jordan 3 shows up as the statement pair when the rest of the outfit is plain. The rotation is the point: each silhouette is a different mood within the same sporty-R&B register.
Why this still matters at the counter
The reason we keep all three of these silhouettes on the shelf at The Closet Inc. is that the customers who walked in for them in 1999 are still walking in for them in 2026 — sometimes the same customers, often their kids. Aaliyah's style moment didn't end when the videos stopped airing. It became a rotation that still works. Timberland 6-inch Wheat boots with a wide-leg pant. Nike Air Force 1 Triple White with anything. Air Jordan 3 Retro with a plain tee and clean denim. The combinations are the same combinations. The silhouettes haven't changed. That's a twenty-five-year run by any measure — and it's the kind of run that defines what we mean when we say a style moment turned into a wardrobe.