See Over 30 Years of Janet Jackson’s Fly Style (2024)

The Cut
By Leah Rodriguez

Janet Jackson reentered the spotlight this fall when her albumUnbreakable came out, but that’s really only one of the reasons to get reacquainted with her style. There are few current fashion trends Jackson doesn’t deserve credit for test-driving in the ‘90s and early ‘00s. The septum piercing popularized by FKA Twigs? Jackson wore one in the safari-themed video for “Together Again”back in 1997. Those fuzzy Nasty Gal sweaters that are everywhere? Jackson, known to play up her tomboy side, paired hers with utility pants. It’s no wonder the actress’sPoetic Justice–era crop top and jean combos still resonate with the Tumblr demographic today — even if they haven’t seen the film.

A star in her own right, Jackson always found ways to set herself apart from pop icon Michael’s style — even if they did both love a good military jacket. Whether she’s wearing one key-hook earring or a single red leather glove, her eye for accessories has been reliably quirky for over 30 years now. Her best accessory, though, might be her own midsection; in the late ‘90s, no one had more ab pride.

See all her best looks in our slideshow ahead, from the straight-out-ofThe Matrix floor-length leather jacket she wore to the 2000 MTV Movie Awards to the many all-white ensembles she’s sported on the red carpet.

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September 20, 2015Where: Performing in Miami. Photo: mpi04/MediaPunch/mpi04/MediaPunch

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June 17, 2015Where: At LAX. Photo: GVK/Bauer-Griffin/2015 Bauer-Griffin

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May 23, 2013Where: At amfAR's Cinema Against AIDS during The Annual Cannes Film Festival. Photo: Vittorio Zunino Celotto/2013 French Select via... May 23, 2013Where: At amfAR's Cinema Against AIDS during The Annual Cannes Film Festival. Photo: Vittorio Zunino Celotto/2013 French Select via Getty Images

See Over 30 Years of Janet Jackson’s Fly Style (8) See Over 30 Years of Janet Jackson’s Fly Style (9)

February 25, 2013Where: With Wissam al Mana and Janet Jackson at the Giorgio Armani fashion show in Milan. Photo: Vittorio Zunino Celotto/2013 ... February 25, 2013Where: With Wissam al Mana and Janet Jackson at the Giorgio Armani fashion show in Milan. Photo: Vittorio Zunino Celotto/2013 Getty Images

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February 22, 2013Where: With Wissam al Mana at the Versace fashion show in Milan. Photo: Venturelli/2013 Venturelli

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May 24, 2012Where: At amfAR's Cinema Against AIDS during the Cannes Film Festival. Photo: Andreas Rentz/2012 Getty Images

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May 10, 2012Where: At the Marco Glaviano Supermodels exhibition opening in New York City. Photo: Jim Spellman/2012 Jim Spellman

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June 26, 2011Where: Performing in Paris. Photo: David Wolff - Patrick/2011 David Wolff - Patrick

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June 14, 2011Where: At the Liaisons Au Louvre II Charity Gala Dinner in Paris, France. Photo: Eric Ryan/2011 Eric Ryan

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May 19, 2011Where: At amfAR's Cinema Against AIDS Gala during the Cannes Film Festival. Photo: George Pimentel/2011 George Pimentel

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March 19, 2011Where: Promoting TRUE YOU: A Guide To Finding And Loving Yourself in New York City. Photo: Eugene Gologursky/2011 Eugene Gologurs... March 19, 2011Where: Promoting TRUE YOU: A Guide To Finding And Loving Yourself in New York City. Photo: Eugene Gologursky/2011 Eugene Gologursky

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February 9, 2011Where: Performing in Jakarta, Indonesia. Photo: Leonard Adam

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November 8, 2010Where: At Women of the Year awards hosted by Glamour Magazine in New York City. Photo: Charles Eshelman/2010 Charles Eshelman

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October 29, 2010Where: At Halloween Extravaganza in New York City. Photo: Steve Mack/2010 Steve Mack

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October 25, 2010Where: At the premiere of For Colored Girls in New York City. Photo: Dimitrios Kambouris/2010 WireImage

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March 22, 2010Where: At the premiere of Why Did I Get Married Too? in New York City. Photo: Jim Spellman/2010 Jim Spellman

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November 22, 2009Where: At American Music Awards in Los Angeles. Photo: Jeff Kravitz/AMA2009

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September 28, 2009Where: At amfAR Milano. Photo: Vittorio Zunino Celotto/2009 Getty Images

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September 13, 2009Where: Performing on MTV Video Music Awards in New York City. Photo: Kevin Mazur/2009 Kevin Mazur

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November 1, 2008Where: Performing during Rock Witchu Tour in New York City. Photo: Brad Barket/2008 Getty Images

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May 13, 2008Where: At Alexander McQueen's Los Angeles Flagship Store Launch Party. Photo: Todd Williamson

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April 26, 2008Where: At GLAAD Media Awards in Hollywood. Photo: Jeff Vespa/2008 Jeff Vespa

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February 14, 2008Where: At NAACP Image Awards in Los Angeles. Photo: Jason Merritt/2008 FilmMagic

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December 4, 2006Where: At Billboard Music Awards in Las Vegas. Photo: Jason Merritt

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October 3, 2006Where: At TAO Las Vegas First Anniversary Weekend Janet Jackson Album Release Party in Las Vegas. Photo: Denise Truscello/Call U... October 3, 2006Where: At TAO Las Vegas First Anniversary Weekend Janet Jackson Album Release Party in Las Vegas. Photo: Denise Truscello/Call U.S. +1-212-686-8900 / U.K. +44-207 659 2815 / Australia +61-2-8262-9222 / Japan: +81-3-5464-7020 or e-mail info@wireimage.

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July 12, 2006Where: At ESPY Awards in Los Angeles. Photo: Michael Caulfield Archive

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June 11, 2006Where: At L.A. Reid's 50th Birthday Party in New York City. Photo: James Devaney

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June 27, 2005Where: With Jermaine Dupri during ASCAP Rhythm & Soul Music Awards in Beverly Hills. Photo: Jean-Paul Aussenard

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February 27, 2005Where: At Vanity Fair Oscar Party in Los Angeles. Photo: J. Merritt

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February 12, 2005Where: With Jermaine Dupri at Pre-GRAMMY Awards Party. Photo: George Pimentel

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August 8, 2004Where: At the Teen Choice Awards. Photo: Jeffrey Mayer/© Jeffrey Mayer 2004 All Rights Reserved

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May 23, 2004Where: At the MTV Video Music Awards Japan in Tokyo. Photo: Jun Sato/Jun Sato

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March 31, 2004Where: Signing copies of Damita Jo in New York City. Photo: KMazur

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March 29, 2004Where: During Virgin Records Presents Damita Jo: A Celebration with Janet Jackson in Honor of Her New Album Arrivals. Photo: Jim ... March 29, 2004Where: During Virgin Records Presents Damita Jo: A Celebration with Janet Jackson in Honor of Her New Album Arrivals. Photo: Jim Spellman

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February 1, 2004Where: During Super Bowl XXXVIII Halftime Show in Houston. Photo: Jeff Kravitz

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June 29, 2004Where: At the Black Entertainment Awards in Hollywood. Photo: Kevin Winter/2004 Getty Images

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June 25, 2002Where: At BET Awards. Photo: L. Cohen

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April 20, 2002Where: At Kids Choice Awards. Photo: KMazur

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March 24, 2002Where: At Vanity Fair Oscar Party Hosted by Graydon Carter in Beverly Hills. Photo: D. Kambouris/Contributing Photographer

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October 15, 2006Where: With Jermaine Dupri during Hollywood Life Movieline Style Awards. Photo: Gregg DeGuire/http://www.wireimage.com

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April 2, 2004Where: On Ryan Seacrest in Hollywood. Photo: Jeff Kravitz

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December 4, 2001Where: At the Billboard Music Awards in Las Vegas. Photo: SGranitz/2001 All Rights Reserved

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September 6, 2001Where: At theMTV Video Music Awards in New York City. Photo: KMazur

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August 22, 2001Where: During All For You World Tour in New York City. Photo: KMazur

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March 10, 2001Where: At MTV Icon: Janet Jackson'. Photo: KMazur

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June 3, 2000Where: At the MTV Movie Awards. Photo: Jeff Kravitz/Jeff Kravitz/FilmMagic.com

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March 29, 1999Where: At the Academy Awards Elton John AIDS Foundation Party. Photo: KMazur

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October 11, 1998Where: With Chris Rock during HBO Presents Janet Jackson's Velvet Rope Party in New York City. Photo: KMazur

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October 10, 1998Where: Performing at Madison Square Garden in New York City. Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.

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March 10, 1998Where: At the Blockbuster Entertainment Awards in Hollywood. Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.

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September 9, 1997Where: At the Virgin Records Party for her new album The Velvet Rope. Photo: Ron Galella, Ltd./1997 Ron Galella, Ltd.

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September 7, 1995Where: With Rene Elizondo at the MTV Video Music Awards in New York City. Photo: Ron Galella, Ltd./1995 Ron Galella, Ltd.

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September 7, 1994Where: At the MTV Video Music Awards in New York City. Photo: Jeff Kravitz/@2005 Jeff Kravitz/FilmMagic.com

See Over 30 Years of Janet Jackson’s Fly Style (108) See Over 30 Years of Janet Jackson’s Fly Style (109)

April 7, 1994Where: With MC Lyte at the party for Janet Jackson's sold-out concert tour and plaque presentation for 10 Million copies of Janet A... April 7, 1994Where: With MC Lyte at the party for Janet Jackson's sold-out concert tour and plaque presentation for 10 Million copies of Janet Album. Photo: Ron Galella, Ltd./1994 Ron Galella, Ltd.

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March 8, 1994Where: With Angela Bassett during Academy Awards Nominees Luncheon in Beverly Hills. Photo: Ron Galella

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February 22, 1994Where: Performing on The Jackson Family Honors. Photo: NBC/2012 NBCUniversal, Inc.

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January 22, 1994Where: With Rene Elizondo at the Golden Globe Awards in Beverly Hills. Photo: Ron Galella, Ltd./1994 Ron Galella, Ltd.

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July 21, 1993Where: With John Singleton during Poetic Justice premiere in Beverly Hills. Photo: Barry King

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February 24, 1993Where: With Michael Jackson at the Grammy Awards in Los Angeles. Photo: Ron Galella, Ltd./1993 Ron Galella, Ltd.

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April 20, 1990Where: Receiving a Hollywood Walk of Fame Star. Photo: Ron Galella, Ltd./1990 Ron Galella, Ltd.

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December 8, 1989Where: At the presentation of platinum records for her album Janet Jackson's Rhythm Nation 1814 and two singles 'Miss You Much' ... December 8, 1989Where: At the presentation of platinum records for her album Janet Jackson's Rhythm Nation 1814 and two singles 'Miss You Much' and 'Rhythm Nation' in Hollywood. Photo: Ron Galella, Ltd./1989 Ron Galella, Ltd.

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January 26, 1987Where: At the American Music Awards in Los Angeles. Photo: Ron Galella/1987 Ron Galella

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January 28, 1985Where: With James DeBarge at the American Music Awards in Los Angeles. Photo: Ron Galella/1985 Ron Galella

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February 28, 1984Where: With La Toya Jackson at the Grammy Awards After Party in Los Angeles. Photo: Ron Galella/1984 Ron Galella

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January 17, 1983Where: At the American Music Awards in Los Angeles. Photo: Ron Galella/1983 Ron Galella

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August 17, 1978Where: At Jackie Jackson's home in Westlake Village, California. Photo: Gregg Cobarr

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