STYLE EVOLUTION

23 of Aaliyah’s Most Iconic Looks


Photographed by Barry King/WireImage

In a 1994 interview with MTV, Aaliyah Dana Haughton appears wearing a signature look: an oversized jacket with leather accents and patches along the sleeves, black shades, a baller watch peeking out as she casually rests her arm on a stack of records. “I dress in my baggy clothes every day, and I am a laid-back person, which is what I portray on camera,” she says in the clip. “It’s really not much of a difference, which is probably why it’s so easy, because it’s really how I am.” Aaliyah’s mellow approach to her personal style extended to her music and acting career, both of which were at their height when she passed away at the age of 22. Naturally exuding cool gave the Detroit native an edge—and star power—that made her stand out against the other artists of her time (“It’s been said that a lot of artists coming out now have similar sounds and they dress similar, and I did want something to set myself apart from everybody else,” she admits coyly in the same interview). Her personal style was part and parcel of that allure; it came to eventually define the trends of the late 1990s and early Aughts. Tiny crop tops, athleticwear, sunglasses of all shapes and colors, exposed underwear (still a trend going strong today,) and baggy men’s-inspired cuts were just some of the styles Aaliyah turned into iconic pieces. On the eve of what would be her 42nd birthday, see some of the musician’s career-defining looks, from Tommy Hilfiger boxers to that pink Baby Phat top.

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Aaliyah backstage at Madison Square Garden for Lifebeat’s Urban Aid benefit concert in New York City, October 1995.

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Aaliyah at the Virgin Megastore in London, May 1995.

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Aaliyah at the 1997 Soul Train Awards in Los Angeles, March 1997.

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Aaliyah at the 1997 Life Tribute Gala in Irvine, Florida, April 2001.

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Aaliyah and Jennifer Love Hewitt at MTV’s Rock n’ Jock basketball game, September 1996.

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Aaliyah at the New York premiere of Anastasia, November 1997.

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Aaliyah at the premiere of Mercury Rising, April 1998.

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Photo by Jeff Kravitz/FilmMagic, Inc.

Aaliyah and Halle Berry during 2000 MTV Movie Awards.

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China Chow, Gwen Stefani, Kidada Jones, Aaliyah, and Rashida Jones at the Fifth Annual RACE to Erase MS, at Century Plaza Hotel in New York City, November 1997.

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Aaliyah at The Forum in Inglewood, California, October 1997.

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Aaliyah at a press conference as Lifebeat’s Counter AID in Los Angeles, November 1994.

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Aaliyah at The Forum in Inglewood, California, October 1997.

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Aaliyah backstage at the fall 2000 Tommy Hilfiger show in Macy’s, New York City, September 2000.

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Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

Aaliyah at the Urbanworld Film Festival Launch Party in New York City, August 2000.

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Aaliyah at the 11th Soul Train Music Awards, held at the Shrine Auditorium in Los Angeles, March 1997.

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Aaliyah at Sean “P. Diddy” Combs’s Independence Day Softball Game and BBQ in East Hampton, New York, July 2001.

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Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

Aaliyah at MTV Celebrates 20th Birthday, held at the Hammerstein Ballroom in New York City, August 2001.

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Aaliyah at the 2000 Teen Choice Awards in Santa Monica, California, August 2000.

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Photo by Jeffrey Mayer/WireImage via Getty Images

Aaliyah at the premiere of “MTV Icon: Janet Jackson,” March 2001.

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Aaliyah at the world premiere of Planet of the Apes, held at Ziegfeld Theater in New York City, July 2001.

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Photographed by Barry King/WireImage via Getty Images

Aaliyah and Jet Li at the premiere of Romeo Must Die in Los Angeles, March 2000.

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Aaliyah at the 2001 Essence Awards, April 2001.

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Aaliyah at a photo shoot in the U.K., February 2001.