Aaliyah Stylist Derek Lee On Creating Her Most Iconic Outfits

Prior to Aaliyah passing, Lee says they were starting to talk about where they wanted her style to go. Lee was leaning toward making Aaliyah look like an anime character, but in a way that read “modern superhero badass” as opposed to costumey comic book character, and mixing those references with elements of Afrofuturism. 

“She was really into that because she was into Japanese culture at the time and liked the idea of looking futuristic,” says Lee. Aaliyah was also working on a Japanese-inspired fashion brand called Dolly Pop with her close friend Kidada Jones, Quincy Jones’ daughter. 

I ask Lee if he would ever use that concept for something else and he immediately says no. 

“It was well thought out and it was ready to go. And it was for that one particular person. And since that one particular person isn’t here, it went away,” says Lee.

BET documented the making of “Rock the Boat” in the Bahamas for its Access Granted series not knowing this would be footage of Aaliyah’s last days. There’s a scene when she and her glam squad, which included Lee, Foreman, and makeup artist Chris Maldonado, are enjoying some off-time by the pool, laughing with Aaliyah as she showed off her yellow bikini and tie-dye sarong. “I’m eating it,” says Aaliyah. While Maldondo and Foreman joined Aaliyah and six other people (​​Anthony Dodd, Scott Gallin, Keeth Wallace, Gina Smith, Douglas Kratz, and the pilot, Luis Morales.) on the small aircraft that would crash, Lee decided to stay behind for a few days. He remembers learning the news while riding around on his scooter and thinking it was a joke. 

“I couldn’t believe God would take away this many people that I loved at once without me feeling it. You would think that you would know the moment it happened. Like something would leave your body. And it didn’t happen like that and it kind of haunted me,” says Lee. “I was driving on my scooter and they said, ‘Yo bro, the plane just crashed.’ And I was just like ‘Fuck you. There’s no way.’ I even said it out loud. And they were like, ‘Nah, man it’s true.’ And I was just like ‘Yeah, whatever.’”

He thought getting back into the swing of things would distract him from grief, so he took a job styling Christina Milian for the “Get Away” music video with Ja Rule, which was shot in Paris. But he quickly realized he wasn’t ready to style again. “As soon as we started shooting by the Eiffel Tower and after getting her dressed and trying things on and being in the trailer, I just kind of broke down. I was like this is too fresh and I need a break,” says Lee.

Eventually he moved to New York to be closer to family and partied to cope with the pain. “I took it out on myself for about two years and I had all my friends around me to help out. I moved back to the LES into a nice apartment with a backyard. So the party was always at my place. It was a lot of fun, but it was debaucherous,” he says. But he eventually transitioned back into working by trading shifts with his mother on B. Smith’s television show, B. Smith Style, which is where he met Lil Kim, who he worked with for her La Bella Mafia album and “The Jump Off” video. Lee says he was trying to make her look less designer-oriented and move her into more custom looks. He worked with Joe LeGrand on pieces like the the Adidas jumpsuit she wore, which they made from an extra large men’s leather sweatsuit. He says he dropped the ball with a pink knockoff Gaultier look. “I can admit I failed on that one,” says Lee.