When it comes to fashion trendsetters of the 90s and early 2000s, Aaliyah was at the top of the list. Babygirl, as she was affectionately known, donned looks that the girls are still trying to recreate decades later. Aaliyah tragically passed away along with eight others in a plane crash in the Bahamas in 2001. She was only 22. Her death left a gaping hole in the music and fashion industries.
Aaliyah’s style has always been described as street but sweet. As she evolved over the years, her outfits started to mature and became more sultry. Her signatures included strappy crop tops, baggy jeans, and fierce shades. Our favorite thing about the artist was that she was never afraid to experiment.
Years after her untimely passing, the world is still obsessed with not only her timeless music but also her unique and versatile fashions.
This year would’ve been the late Princess of R&B’s 45th birthday (Jan. 15). In honor of her birthday, we are celebrating Aaliyah’s legacy by remembering some of her most iconic looks. You’ll be dying to add these to your fashion boards.
1. Her Roberto Cavalli dress is still talked about.
Aaliyah was best known for her streetwear aesthetic. She always straddled the line between tomboyish and girly; however, at the 2000 VMAs, she went full glam. Aaliyah stepped onto the red carpet in a long yellow and black Roberto Cavalli slip dress with a feather-trimmed slit. Since the dress was such a bold statement, she wore strappy heels and went minimal on the accessories and makeup.
In i-D’s September 2001 issue, the singer gushed about Cavalli to Glen Caldron, calling him her favorite designer.
“His clothes seem to be made for me,” she told the publication. “They just scream Aaliyah.”
2. Her denim TRL one-piece was too good.
The sultry songbird slayed in Roberto Cavalli once again while hosting the video countdown show “TRL” in 2000. The denim jumpsuit was one of the artist’s best outfits; sexy cutouts and gold embellishments on the pant leg elevated the look. Her accessories included a gold body chain, a pair of Timberlands, and chic oval sunglasses. Around this time, Aaliyah worked with stylist Derek Lee to upgrade her tomboyish style with high-end brands.
3. Aaliyah’s “Try Again” look has stood the test of time.
Perhaps one of her more popular looks to date, Aaliyah’s “Try Again” music video fit, is still being replicated to this day. In the video, she wore a Dolce & Gabbana diamante bra, a choker, leather pants, and black eyeshadow. Multiple celebrities, such as Keke Palmer and Olay Noel, have recreated this look for Halloween.
4. She was the Queen of serving “TRL” looks.
There are no words to describe how timeless this look still is. While hosting “TRL” in 2000, Aaliyah slipped into this all-white ensemble backstage. She donned an icy white faux fur jacket from Rifat Özbek’s Fall 1997 collection. The jacket paired perfectly with matching white pants with slits on the sides.
5. Her “Rome Must Die” premiere look was glamorous.
The year 2000 was such a huge year for the pop star, and it was when she served some of her best looks. For the premiere of her first starring movie role in “Romeo Must Die,” she sported a sexy embellished sheer top with a knee-length silhouette. She layered it with straight-legged pants and Black open-toed sandals.
6. A baggy look was her signature.
Nobody rocked a crop top and baggy jeans like the “Rock the Boat” singer. It was her signature look, and she wore it well. Her outfit for her 1997 performance at The Forum in California was classic Aaliyah. It was tomboyish yet sexy. The look featured a mix of strappy attire, gothic leather, metallics, and red vinyl. The singer effortlessly pulled off the look with confidence.
7. She was THE Tommy Hilfiger girl.
Aaliyah donned another sexy, baggy look while performing at The Forum in LA. This time she wore a yellow Tommy Hilfiger look paired with round shades. Aaliyah was the premier Tommy Hilfiger girl, becoming the face of the brand in 1996. She helped to popularize the brand’s streetwear collection, and it’s one of her greatest sartorial legacies to date.
8. Aaliyah wore her first dress at the Academy Awards.
In 1998, the singer made history as the youngest celebrity to perform at the Oscars. She also made personal history that night, too. It was the first time she’d worn a dress on the red carpet. The sleek black dress complimented her frame perfectly. She paired them with a pair of simple black heels. Primarily, Aaliyah always stuck to her tomboy roots, opting to wear pants. However, in a 2011 interview with BET’s 10th anniversary TV special, “Aaliyah: One in a Million,” Missy Elliot shared a memory of her and Aaliyah making a bet on who would wear a dress first. Obviously, baby girl lost.
9. She was a pro at effortless beauty looks.
The star’s outfit at the “Planet of the Apes” premiere in 2001 is one of her most underrated. She walked the carpet in white low-rise jeans, an ultra-feminine chiffon blouse, and a gold chain belt draped around her hips. She completed the look with strappy sandals and beautiful beach waves.
10. She looked flawless at the Essence Awards.
By now, we all know that Aaliyah had a major obsession with Roberto Cavalli. Her Cavalli looks were among some of her best. Her dress for the 2001 Essence Awards was flawless. She stunned in the feather-printed silk gown, complete with a bustier.
Aaliyah’s looks, like her music, will always stand the test of time. It was because of her and her team’s forward-thinking, we are sure to see replicas of her outfits for years to come.
Which Aliyah outfit is your favorite? Comment and let us know!
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