Aaliyah’s Stylist Derek Lee on Her Most Iconic Fashion Moments

Singer and actress Aaliyah Haughton walked so that the likes of Bella Hadid, Hailey Baldwin, and Aleali May, could run. A pioneer of oversized proportions and a sporty-chic aesthetic, Baby Girl (as she was also known) continues to make fashion waves decades after her untimely passing. She had ongoing brand relationships that far predate social media and influencer culture. But it’s the late star’s effortless style that has cemented her as a forever fashion icon.

Aaliyah’s stylist, Derek Lee, describes the singer’s vibe to BAZAAR as “confident, comfortable, effortless street style,” adding, “That’s what makes it timeless.” When she first showed up on the scene at the age of 14, Aailyah had an easy swag about her—sticking close to Tommy Hilfiger sweat suits (of which she later became a brand ambassador) and strap-detailed bra tops that later gave birth to the midriff-flossing trend. As her look evolved over the years, the “I Care 4 U” singer managed to stay true to her sportier aesthetic but with a chic, fashion-forward edge. From Roberto Cavalli and Dolce & Gabbana to Azzedine Alaïa, the native New Yorker was the epitome of the phrase It girl.

Lee attributes the most recent Aaliyah admiration with the undeniable shift we’ve seen in the way women are dressing—especially since the beginning of the pandemic. “People really want to be comfortable,” the celebrity stylist explains. “Baggy clothing is comfy, and that’s why I think people are gravitating to it at the moment.” Exaggerated proportions aside, other details and pieces that come to mind when we think of the "Back and Forth" singer include low-rise jeans, bandana headbands, and slinky tanks or crop tops—all quintessential styles from the '90s.

“We often didn’t do fittings prior to our shoots,” Lee divulges on working with the icon. “She would describe to me how she wanted to be portrayed in a specific shoot, and I would then shop it. I knew her style like the back of my hand and would always bring more than I needed. When I would get to the shoot, she would always ask me what my favorite was, and nine times out of ten, that’s what she would wear.”

Ahead, see the best of Aaliyah’s looks, which prove she’s as relevant in the fashion industry today as she was during her heyday—and shop key pieces.