By: Jackson Howard

14 years ago this month, on August 25th 2001, Aaliyah lost her life in a tragic plane crash. A multi-platinum singer, renowned dancer, budding actress and groundbreaking style icon, Baby Girl – as she was lovingly known – was only 22 years old. One of pop culture’s greatest losses, Aaliyah’s legacy nonetheless persists, from scores of Tumblr and Pintrest pages, to record sales – over 52 million globally – to public adoration from artists like Drake and her longtime friend Missy Elliott, to her influence on artists like Rihanna, Ciara and Beyoncé.

For all her music, acting and dancing, Baby Girl’s style was – and still is – just as important. Most notable was her love of denim, specifically from Tommy Hilfiger, for whom she served as a spokeswoman and catwalk model. Resisting the pressure to overly-sexualize herself in the manner of other female singers, Aaliyah broke ground by wearing the baggy menswear outfits of her male R&B counterparts while maintaining her sex appeal.

Aaliyah combined tight sports bras with loose-fitting Hilfiger denim jeans and overalls, Timberland work boots, Tommy boxers, jean jackets, bandanas and futuristic sunglasses to create an iconic ’90s look that was nonetheless her own and helped establish Hilfiger as a heritage American brand. She was the pop-star next door, accessible and relatable to her fans while simultaneously mysterious and seductive enough to make the public want more. Her iconic baggy Hilfiger denim and work boots look – part construction worker, part sexy R&B star – challenged the public’s and urban music’s perception of gender and its relation to clothing, especially in terms of whether style “belonged” to a certain gender.

While probably one of the most remembered Hilfiger brand reps from the 1990s, Aaliyah wasn’t the only musician featured by the line. Usher, Destiny’s Child, TLC and Snoop Dogg are some of the artists that worked with and adopted Hilfiger in the ’90s during the peak of the brand’s association with rap and R&B stars, a partnership that created serious profit and cultural legitimacy for Hilfiger.

As a fashion and denim icon, Aaliyah created a different kind of heritage, a grab-bag of menswear, American denim and playfulness that pushed stylistic and cultural boundaries while laying a long-lasting foundation for decades to come. Her partnership with Hilfiger and her love of denim have both remained integral parts of her legacy today and continue to influence countless fans, artists and fashion icons. Taking from one of her best-known songs, Aaliyah truly was “One in a Million.”