See Over 30 Years of Janet Jackson’s Fly Style
Janet Jackson reentered the spotlight this fall when her album Unbreakable 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’s Poetic 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-of The 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.
September 20, 2015 Where: Performing in Miami. Photo: mpi04/MediaPunch/mpi04/MediaPunch
June 17, 2015 Where: At LAX. Photo: GVK/Bauer-Griffin/2015 Bauer-Griffin
May 23, 2013 Where: At amfAR's Cinema Against AIDS during The Annual Cannes Film Festival. Photo: Vittorio Zunino Celotto/2013 French Select via...
May 23, 2013 Where: At amfAR's Cinema Against AIDS during The Annual Cannes Film Festival. Photo: Vittorio Zunino Celotto/2013 French Select via Getty Images
February 25, 2013 Where: With Wissam al Mana and Janet Jackson at the Giorgio Armani fashion show in Milan. Photo: Vittorio Zunino Celotto/2013 ...
February 25, 2013 Where: With Wissam al Mana and Janet Jackson at the Giorgio Armani fashion show in Milan. Photo: Vittorio Zunino Celotto/2013 Getty Images
February 22, 2013 Where: With Wissam al Mana at the Versace fashion show in Milan. Photo: Venturelli/2013 Venturelli
May 24, 2012 Where: At amfAR's Cinema Against AIDS during the Cannes Film Festival. Photo: Andreas Rentz/2012 Getty Images
May 10, 2012 Where: At the Marco Glaviano Supermodels exhibition opening in New York City. Photo: Jim Spellman/2012 Jim Spellman
June 26, 2011 Where: Performing in Paris. Photo: David Wolff - Patrick/2011 David Wolff - Patrick
June 14, 2011 Where: At the Liaisons Au Louvre II Charity Gala Dinner in Paris, France. Photo: Eric Ryan/2011 Eric Ryan
May 19, 2011 Where: At amfAR's Cinema Against AIDS Gala during the Cannes Film Festival. Photo: George Pimentel/2011 George Pimentel
March 19, 2011 Where: Promoting TRUE YOU: A Guide To Finding And Loving Yourself in New York City. Photo: Eugene Gologursky/2011 Eugene Gologurs...
March 19, 2011 Where: Promoting TRUE YOU: A Guide To Finding And Loving Yourself in New York City. Photo: Eugene Gologursky/2011 Eugene Gologursky
February 9, 2011 Where: Performing in Jakarta, Indonesia. Photo: Leonard Adam
November 8, 2010 Where: At Women of the Year awards hosted by Glamour Magazine in New York City. Photo: Charles Eshelman/2010 Charles Eshelman
October 29, 2010 Where: At Halloween Extravaganza in New York City. Photo: Steve Mack/2010 Steve Mack
October 25, 2010 Where: At the premiere of For Colored Girls in New York City. Photo: Dimitrios Kambouris/2010 WireImage
March 22, 2010 Where: At the premiere of Why Did I Get Married Too? in New York City. Photo: Jim Spellman/2010 Jim Spellman
November 22, 2009 Where: At American Music Awards in Los Angeles. Photo: Jeff Kravitz/AMA2009
September 28, 2009 Where: At amfAR Milano. Photo: Vittorio Zunino Celotto/2009 Getty Images
September 13, 2009 Where: Performing on MTV Video Music Awards in New York City. Photo: Kevin Mazur/2009 Kevin Mazur
November 1, 2008 Where: Performing during Rock Witchu Tour in New York City. Photo: Brad Barket/2008 Getty Images
May 13, 2008 Where: At Alexander McQueen's Los Angeles Flagship Store Launch Party. Photo: Todd Williamson
April 26, 2008 Where: At GLAAD Media Awards in Hollywood. Photo: Jeff Vespa/2008 Jeff Vespa
February 14, 2008 Where: At NAACP Image Awards in Los Angeles. Photo: Jason Merritt/2008 FilmMagic
December 4, 2006 Where: At Billboard Music Awards in Las Vegas. Photo: Jason Merritt
October 3, 2006 Where: At TAO Las Vegas First Anniversary Weekend Janet Jackson Album Release Party in Las Vegas. Photo: Denise Truscello/Call U...
October 3, 2006 Where: 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.
July 12, 2006 Where: At ESPY Awards in Los Angeles. Photo: Michael Caulfield Archive
June 11, 2006 Where: At L.A. Reid's 50th Birthday Party in New York City. Photo: James Devaney
June 27, 2005 Where: With Jermaine Dupri during ASCAP Rhythm & Soul Music Awards in Beverly Hills. Photo: Jean-Paul Aussenard
February 27, 2005 Where: At Vanity Fair Oscar Party in Los Angeles. Photo: J. Merritt
February 12, 2005 Where: With Jermaine Dupri at Pre-GRAMMY Awards Party. Photo: George Pimentel
August 8, 2004 Where: At the Teen Choice Awards. Photo: Jeffrey Mayer/© Jeffrey Mayer 2004 All Rights Reserved
May 23, 2004 Where: At the MTV Video Music Awards Japan in Tokyo. Photo: Jun Sato/Jun Sato
March 31, 2004 Where: Signing copies of Damita Jo in New York City. Photo: KMazur
March 29, 2004 Where: During Virgin Records Presents Damita Jo: A Celebration with Janet Jackson in Honor of Her New Album Arrivals. Photo: Jim ...
March 29, 2004 Where: During Virgin Records Presents Damita Jo: A Celebration with Janet Jackson in Honor of Her New Album Arrivals. Photo: Jim Spellman
February 1, 2004 Where: During Super Bowl XXXVIII Halftime Show in Houston. Photo: Jeff Kravitz
June 29, 2004 Where: At the Black Entertainment Awards in Hollywood. Photo: Kevin Winter/2004 Getty Images
June 25, 2002 Where: At BET Awards. Photo: L. Cohen
April 20, 2002 Where: At Kids Choice Awards. Photo: KMazur
March 24, 2002 Where: At Vanity Fair Oscar Party Hosted by Graydon Carter in Beverly Hills. Photo: D. Kambouris/Contributing Photographer
October 15, 2006 Where: With Jermaine Dupri during Hollywood Life Movieline Style Awards. Photo: Gregg DeGuire/http://www.wireimage.com
April 2, 2004 Where: On Ryan Seacrest in Hollywood. Photo: Jeff Kravitz
December 4, 2001 Where: At the Billboard Music Awards in Las Vegas. Photo: SGranitz/2001 All Rights Reserved
September 6, 2001 Where: At the MTV Video Music Awards in New York City. Photo: KMazur
August 22, 2001 Where: During All For You World Tour in New York City. Photo: KMazur
March 10, 2001 Where: At MTV Icon: Janet Jackson'. Photo: KMazur
June 3, 2000 Where: At the MTV Movie Awards. Photo: Jeff Kravitz/Jeff Kravitz/FilmMagic.com
March 29, 1999 Where: At the Academy Awards Elton John AIDS Foundation Party. Photo: KMazur
October 11, 1998 Where: With Chris Rock during HBO Presents Janet Jackson's Velvet Rope Party in New York City. Photo: KMazur
October 10, 1998 Where: Performing at Madison Square Garden in New York City. Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
March 10, 1998 Where: At the Blockbuster Entertainment Awards in Hollywood. Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
September 9, 1997 Where: At the Virgin Records Party for her new album The Velvet Rope. Photo: Ron Galella, Ltd./1997 Ron Galella, Ltd.
September 7, 1995 Where: With Rene Elizondo at the MTV Video Music Awards in New York City. Photo: Ron Galella, Ltd./1995 Ron Galella, Ltd.
September 7, 1994 Where: At the MTV Video Music Awards in New York City. Photo: Jeff Kravitz/@2005 Jeff Kravitz/FilmMagic.com
April 7, 1994 Where: 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, 1994 Where: 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.
March 8, 1994 Where: With Angela Bassett during Academy Awards Nominees Luncheon in Beverly Hills. Photo: Ron Galella
February 22, 1994 Where: Performing on The Jackson Family Honors. Photo: NBC/2012 NBCUniversal, Inc.
January 22, 1994 Where: With Rene Elizondo at the Golden Globe Awards in Beverly Hills. Photo: Ron Galella, Ltd./1994 Ron Galella, Ltd.
July 21, 1993 Where: With John Singleton during Poetic Justice premiere in Beverly Hills. Photo: Barry King
February 24, 1993 Where: With Michael Jackson at the Grammy Awards in Los Angeles. Photo: Ron Galella, Ltd./1993 Ron Galella, Ltd.
April 20, 1990 Where: Receiving a Hollywood Walk of Fame Star. Photo: Ron Galella, Ltd./1990 Ron Galella, Ltd.
December 8, 1989 Where: At the presentation of platinum records for her album Janet Jackson's Rhythm Nation 1814 and two singles 'Miss You Much' ...
December 8, 1989 Where: 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.
January 26, 1987 Where: At the American Music Awards in Los Angeles. Photo: Ron Galella/1987 Ron Galella
January 28, 1985 Where: With James DeBarge at the American Music Awards in Los Angeles. Photo: Ron Galella/1985 Ron Galella
February 28, 1984 Where: With La Toya Jackson at the Grammy Awards After Party in Los Angeles. Photo: Ron Galella/1984 Ron Galella
January 17, 1983 Where: At the American Music Awards in Los Angeles. Photo: Ron Galella/1983 Ron Galella
August 17, 1978 Where: At Jackie Jackson's home in Westlake Village, California. Photo: Gregg Cobarr
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