Aaliyah's Coolest Outfits - Aaliyah Style

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MTV Awards, 2000

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“I was on an extended vacation in Italy [when I] got an email from my agent about Aaliyah wanting to go to the MTV Awards, [asking] if I would be able to bring some things by for her to see,” the stylist to the stars explains on how one of her most iconic looks came to fruition. “It was a last-minute request, and I was on holiday, so I called [Roberto] Cavalli in New York City and had an assistant both shop on his own, pick up, and do a fitting with Aaliyah. He met her at the hotel; Aaliyah immediately asked what I had specifically picked out for her, which ended up being the yellow-and-black dress.” -Derek Lee

Rat and Boa Fabienne Dress

If you’re hoping to re-create one of Aaliyah’s most iconic looks, Rat and Boa’s Fabienne Dress is a chic alternative (especially considering the vintage Roberto Cavalli piece is impossible to find).

Planet of the Apes World Movie Premiere, 2001

planet of the apes world premiere aaliyah

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Low-rise jeans were spiking to popularity in the early 2000s, and there’s no denying that Aaliyah’s personal style had something to do with it. The singer sported a skinny white pair on the red carpet, dressing them up with a romantic chiffon blouse and luxe accessories like a chain belt draped across her hips. Reminiscent of something we’d see the likes of Bella Hadid wearing, this look was completed with a strappy sandal and loose beach waves.

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Rag & Bone Dre Low-rise Slim Boyfriend Jeans

Embrace the low-rise jean resurgence with a cropped, white pair that can be worn with just about anything.

Essence Awards, 2001

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Aaliyah was somewhat known for wearing Roberto Cavalli’s gowns to red-carpet events. Though the black-and-yellow zebra-print ensemble she wore the year prior is more famously known, her feather-printed silk gown—complete with a bustier—by the luxury label is just as good. In addition to her business relationship with fashion brand Tommy Hilfiger, the singer-turned-actress and her stylist had quite a thing for Cavalli.

Roberto Cavalli Printed Silk Corseted Trained Evening Dress

Part of the fall/winter 2001 collection, this vintage silk gown from Roberto Cavalli is a dead ringer for the style that she wore to the Essence Awards 20 years ago.

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MTV 20th Anniversary, 2001

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Staying true to her laid-back style, the singer sported a pair of low-rise jeans in a medium wash with a leather laser-cut bustier. Known for her ability to find that balance between effortless and chic, she truly embodied her approach to fashion with this look.

Alaïa Editions Leather Bustier Top

For a more modern take on her ensemble, consider investing in Alaïa’s bustier top with crisscross details.

Romeo Must Die Premiere, 2000

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For the premiere of the star’s breakout movie role, Romeo Must Die, she wore an embellished sheer top with a knee-length silhouette. The singer layered it over straight-leg pants with flat sandals to balance the glamorous feel. This is a great example of how to pull off wearing a dress over pants without it feeling too bulky or mismatched.

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Dion Lee Sheer Asymmetric Dress

Now 40% Off

Dion Lee’s sheer dress is perfect for layering over tailored pants and a second-skin camisole a la Aaliyah.

Anastasia Movie Premiere, 1997

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Before Hailey Bieber wore Bottega’s fringed shearling coat with baggy jeans while out and about in New York City, Aaliyah sported the combo in all white on the red carpet in the late '90s. Though one of her earlier ensembles, the look set the tone for the more effortless approach to glam that the star would take as her career continued to blossom. Now, it’s become one of her most distinct looks.

P.A.R.O.S.H. Shearling Long Length Coat

Follow the singer’s lead and style an oversized shearling coat with a crop top and baggy jeans. (Sneakers encouraged but not required.)

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The Forum, 1997

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In quintessential Aaliyah fashion, the singer sported a pair of baggy vinyl pants—Calvin Klein boxers exposed, of course—for her 1997 performance at The Forum in Los Angeles. But it's the body wrapping, bikini-style top she wore with it that cemented her status as the ultimate trendsetter. With the midriff-flossing trend making a big comeback for summer 2021, the Romeo Must Die star served up ample inspiration for fans to pull from.

Christopher Esber Outline Tie Bikini Top

When you think of the midriff-flossing trend that’s on the rise right now, its likely that Christopher Esber comes to mind. Embrace the comeback with its triangle bikini top that can be tied multiple times around the waist.

Shelby Ying Hyde is a Brooklyn-based shopping and fashion contributor BAZAAR.com, with bylines on The Zoe Report, Teen Vogue, Essence, Nylon, Elite Daily and more. Prior to entering the editorial space, she worked at luxury e-commerce giants Net-a-Porter and Moda Operandi on the product editorial team, where she gained an extensive understanding of the luxury market as it pertains to shopping and engaging customers in a digital space. Follow @theshelbyying on Instagram for shopping advice, sale updates, and tips for building a well-rounded wardrobe.