Aaliyah’s Style Evolution: See Her Most Timeless and Influential Looks

These days, ‘90s pop culture is having a moment so what better time to reflect on one of its brightest stars: Aaliyah.

Out of all the sensational artists the ‘90s and early 2000s have blessed us with, only a few still have lasting influence today. It may have been two decades since her tragic passing, but, aside from her music, Aaliyah’s impact is still also seen in the latest fashion trends.

Aaliyah’s legacy is so timeless because she mastered the art of simplicity. She was a style chameleon who looked just as radiant in a pair of baggy pants as she did in a glamorous red carpet gown. Her music video looks were ultra-fierce and featured all the cut-outs and sparkles that fill our Insta feeds today. We also can’t gloss over the fact that she made streetwear and oversized clothing cool in an era when skin-tight was everything.

From her signature makeup to her “tomboy” edge, Aaliyah’s influence is undeniable and has no sign of stopping any time soon. Here, we look back on the princess of R&B’s best looks and the stars she’s inspired over the years.

The Slip Dress

Aaliyah looked fierce wearing a yellow zebra print Roberto Cavalli dress at the 2000 MTV Music Awards. The gown’s high thigh split and feathered trim add extra drama and till this day we can’t go over how good she looks. In April 2021, model Paloma Elsesser wore the same statement dress to a wedding and it still looked great more than two decades later. Talk about timeless.

Leather

As Aaliyah’s music matured, so did her look. In her music video for “One In A Million,” she wore figure-hugging pieces in tactile textures like leather. Normani recently rocked a similar look in her music video for “Wild Side.” Normani's song pays homage to “One in a Million” in more ways than one. Normani sampled Aaliyah’s track and recreated parts of her music video choreography. When it comes to styling, Normani served some major energy in her laser cut-out ensemble.

Monochrome

Normani also gave a modern spin to Aaliyah’s iconic all-white outfit in “One In A Million.” Aaliyah performs her clean choreography wearing one of her simplest looks: a white crop top and belly button piercing with matching baggy pants. Aaliyah’s minimalist style has aged just as well as her futuristic sound.

All Black Everything

When in doubt, black always works. Aaliyah knew this all too well since, after white, black was her go-to color. Black is sultry and mysterious which perfectly captures what made Aaliyah such an enigma.

The Bandana

Thankfully, a lot of Aaliyah’s staple accessories are back en vogue. The classic print bandana can elevate any casual outfit. Just take a look at singer Becky G’s white paisley ‘fit she wore during a virtual festival performance in May. Her monochrome look and silver jewelry have Aaliyah’s name written all over it.

The “Try Again” Effect

Aaliyah’s iconic look from her “Try Again” music video still has a hold on pop culture today. She looked icy as ever wearing a diamond choker with a matching bra and belt. Kim Kardashian controversially recreated this look for Halloween back in 2017 and Keke Palmer wore her own stunning version of Aaliyah’s outfit for Halloween in 2015. Aaliyah really is the blueprint.

Tommy Hilfiger

It’s impossible to look back on Tommy Hilfiger’s ‘90s heyday without bringing up Aaliyah. She constantly wore the brand and was featured in a 1996 Tommy Jeans campaign. Aaliyah’s loyalty to the brand stills influences fashion today. Last spring, Yara Shahidi recreated Aaliyah’s Tommy Jeans look in an episode of Grown-ish. She even wore Timbs and a side part to match.

Timberlands

Speaking of Timbs, that's a shoe that needs to make a mainstream comeback. Aaliyah only ever wore heels for the red carpet. Day to day she opted for sneakers or a trusty Timberland boot. Check out her crystal white pair that perfectly match her look.

Oversized Layering

When Aaliyah started out she was, using ‘90s nomenclature, the ultimate tomboy. The more layers, the cooler the look. Her oversized outfit still holds up today, with Bella Hadid spotted in a very similar chocolate leather vest worn over a white shirt. Aaliyah’s pic is from 1994 and Bella's from 2020 but the resemblance fashion-wise is uncanny – down to the pockets, even.

Camo

Aaliyah’s outwear was always on point. As usual, oversized was her go-to, and celebs today are still trying to capture her effortless take on casual wear. Rihanna was spotted wearing a similar reverse camo jacket in New York back in 2017. Kylie Jenner is also a fan. She’s been papped and posted on Instagram wearing the same Canada Goose x Vetements collab.

Denim

If there’s one word to describe Aaliyah’s style, it’s versatility. Her everyday looks have as much of a hold on fashion today as her glamorous music video moments. Take Aaliyah’s denim overall crop top. Back in 2013, Rihanna collaborated on a collection with the British fast-fashion brand River Island. Rihanna knows a style icon when she sees one and clearly had Aaliyah pinned to her mood board.

Logomania

Wearing logos is a good way to keep your name in the history books. Aaliyah is synonymous with the brands she wore – and this particular outfit is one of her most unforgettable. She took to the stage wearing a matching Tommy Hilfiger sweatsuit in canary yellow with a silver lining. Today, Billie Eilish is known for wearing oversized logo sets that Aaliyah would surely be proud of.

The Boyfriend Fit

Aaliyah revolutionized what it meant to be a stylish woman in the ‘90s by taking inspiration from menswear. In an era when her pop peers were serving skin-tight glam, Aaliyah embraced roomy streetwear.

Bikini Tops

The more Aaliyah grew as a star, the more experimental her wardrobe became. She still stuck to her sartorial roots by wearing Calvin Klein boxer shorts that peaked above her low-rise pants, but her red patent jacket and metallic crossover bikini top gave a stage-ready twist.

Statement Sunglasses

It wouldn’t be a journey down Aaliyah’s greatest looks without mentioning her love for a pair of tinted sunglasses. Her lavish vizor pair are as Y2K as it gets, featuring a fuchsia tint and gold rim. No matter the preferred shape, Aaliyah’s taste in eyewear is immaculate. Back in 2019, Kylie Jenner celebrated her 22nd birthday wearing a huge pair of Aaliyah-esque white sunnies.

Cut-outs

Cut-outs are having a major moment in 2021 and, back in the day, Aaliyah was also all over them. Her low-rise white pants paired with a tiny shoulder bag are the epitome of '00s chic but it’s the subtle touches of gold bling that make this look a winner.

Motorsport

Aaliyah was always the image of sophistication but especially when she indulged in her love for motorsport fashion. In her music video for 2000 hit “Try Again,” she wore a white Chanel ensemble with a classic silver Chanel belt. What’s not to love?

Baggy Pants

Aaliyah was all about the slouch. Her pants always sat low on her waist and draped effortlessly over her sneakers. It’s the ultimate comfy casual look.

Futurism

At the start of the millennium, the world’s obsession with new technology began to make its mark on fashion. Aaliyah captured the futuristic outlook of her time in her “Are You That Somebody” music video. Dressed in a grey mesh top and silver boxers, she looked like a space-age goddess. Plus, no one could pull off iridescent green lipstick quite like her.

Tomboy Chic

When it comes to her style, Aaliyah always stayed true to herself. In an appearance on the Jay Leno show in 1997, she performed in a khaki boiler suit and The Matrix-inspired sunnies and looked badass while doing it.

Icy Jewelry

Dare we say that Aaliyah is the original Icy Girl? Aaliyah’s understated color palette meant her jewelry had plenty of room to shine. She had a thing for silver and often rocked an iced-out chain around her neck.

Sportswear

In Aaliyah’s early days, she always made comfort a priority. Here she is making an appearance in London back in 1995. Her sports jersey is a world away from the cropped leather looks she adopted later in her career.

A Bare Midriff

The early 2000s were infamous for everyone’s obsession with low-rise pants and cropped shirts. High waist pants were nowhere to be seen and Aaliyah’s washboard abs became a fashion statement in their own right.

Asymmetric tops

It’s clear by now that Aaliyah loved a crop top. From the simple tank to the racy cut-out, no style was off-limits. This asymmetric watercolor top is a dreamy take on her closet staple.

“We Need A Resolution”

Aaliyah served multiple looks in her “We Need A Resolution” music video but this one takes the cake as the most avant-garde. She wore a python (and a few extra snakes) to match her ‘fit, and for that, we commend her.

Co-Ords

You could almost always catch Aaliyah in a matching set. Her cyber blue co-ord from “We Need A Resolution” lives in my head rent-free.

Red Carpet Glam

Aaliyah looked radiant wearing a beige embroidered corset dress to Madison Square Garden in New York. It’s safe to say that Aaliyah’s red carpet looks were perfection and this gown was no exception.

Belly Chains

Aaliyah’s love for sparkle extended to her body jewelry. She let her silver chain sit just above jeans and, frankly, with abs like that who wouldn’t?

Hats

Aaliyah’s final music video “Rock the Boat” took place in a tropical paradise and her looks did not disappoint. She switched her usual streetwear attire for beach-ready sarongs, a warmer color palette, and one of the most popular styles of the time: a baker boy cap.

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Originally Appeared on Teen Vogue