American singer Janet Jackson, circa 1990. (Photo by Tim Roney/Getty Images)
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Janet Jackson’s Style Evolution, From Child Actress to Iconic Pop Star

A true icon in every sense of the word.

Janet Jackson is an icon in every sense of the word. Before she was racking up awards, hitting the big screen, and selling out stadiums, she started out as an adorable child actor. From Good Times to The Velvet Rope and beyond, see her best fashion moments through the years.

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1977, American Music Awards

In 1977, heading to the American Music Awards, Jackson admires her older brother Michael wearing a white trench coat with a red jumpsuit underneath.

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1983, The R&B Awards

Heading to the R&B Awards in 1983, Jackson wore a pale pink blazer with a bright red bow tie and a gold key on one hoop earring.

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1983, American Music Awards

Arriving at the 1983 10th Annual American Music Awards Jackson wore a red strapless, tiered gown.

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1984, Grammy Awards After Party

In 1984, Jackson arrived to the 26th Annual Grammy Awards After Party with her sister LaToya Jackson, wearing a red oversized blazer rolled up with a crystal brooch as a bowtie.

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1985, American Music Awards

At the 12th Annual American Music Awards in 1985, Jackson wore a white velvet and tiered gown posing next to her sister LaToya and singer Kenny Rogers.

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1987, American Music Awards

At the 14th Annual American Music Awards in 1987, Jackson wore a black wool suit with a silver brooch and leather gloves.

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1988, American Cinema Awards

At the 1988 American Cinema Awards, Jackson wore a light gray moto jacket over an all-black outfit with high-waisted harem pants.

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1990, American Music Awards

After winning two awards at the 1990 17th Annual American Music Awards, Jackson wore a bright pink shirt underneath a classic black waist coat.

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1990, Hollywood Walk of Fame

In 1990, Jackson was honored with her own star on the Hollywood Walk of Fame wearing her iconic Rhythm Nation costume from 1989.

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1993, GRAMMY Awards

Leaving the 1993 35th Annual Grammy Awards, Jackson wore a double-breasted white pantsuit with a white hair wrap to match.

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1994, MTV Video Music Awards

In 1994, at the MTV VMA's Jackson took a break from her suits with denim overalls and a black baseball cap.

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1995, MTV Video Music Awards

Jackson wore tailored high-waisted black pants with a cropped white v-neck polo shirt that read "pervert" on the back at the 1995 MTV VMA's.

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1997, The Velvet Rope Album Release Party

Keeping it tailored at the top, Jackson wore a sharp blazer with a satin skirt to her 1997 The Velvet Rope album release party.

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1998, Blockbuster Awards

At the 1998 4th Annual Blockbuster Awards, Jackson wore a black cropped fuzzy cardigan with tan cargo pants and chunky sole boots.

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1999, Academy Awards

At the 71st Annual Academy Awards in 1999, Jackson wore a black square-neck crop top with a black ballgown skirt.

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2000, MTV Movie Awards

Serving serious Matrix vibes, Jackson showed up to the 2000 MTV Movie Awards in an all-leather, floor-length look.

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2001, Billboard Music Awards

Arriving at the 2001 Billboard Music Awards, Jackson served bohemian vibes in a black lace crop top with a dark purple skirt and western boots.

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2001, MTV Video Music Awards

Arriving at the 2001 MTV VMA's, Jackson wore a sheer mini dress with sequin embellishments, a pink baker boy hat, and black thigh-high leather boots.

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2004, BET Awards

Arriving at the 2004 BET Awards, Jackson wore a backless cream-colored fishtail gown.

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2005, Pre-GRAMMY Awards Party

Arriving at the Clive Davis' Pre-GRAMMY Awards Party with Jermaine Dupri, Jackson wore a pink dress with hot pink boots.

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2005, Vanity Fair Oscar Party

Arriving with Dupri to the 2005 Vanity Fair Oscar Party, Jackson wore a white off-the-shoulder gown with fur-accented sleeves.

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2006, CFDA Awards

Arriving to the 2006 CFDA Awards, in a red halter gown with a black belt.

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2008, GLAAD Media Awards

In 2008, Jackson arrived to the GLAAD Media Awards wearing a white tailored jumpsuit with a pink pinstriped collared shirt with a matching pocket handkerchief.

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2009, amfAR's Inaugural Milan Fashion Week Event

In 2009, Jackson arrived amfAR's Milan Fashion Week Even wearing a royal blue floor-length gown with a subtle slit.

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2010, Why Did I Get Married? Preview Screening

In 2010, co-star Jackson arrived to her movie screening for Why Did I Get Married? wearing a gray sheer off the top with a tight black midi skirt.

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2011, amfAR Cinema Against AIDS

In 2011, Jackson showed up to the amfAR Cinema Against AIDS events in a silk olive green top with a floor-length burgundy skirt.

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2012, Supermodels Exhibition Opening

In 2012, Jackson wore an embellished corset-style jacket with faded black jeans and black booties in New York City.

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2012, amfAR's Cinema Against AIDS

In 2013, Jackson arrived at the amfAR's Cinema Against AIDS event, in a white jogger pantsuit.

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2015, BET Awards

At the 2015 BET Award show, Jackson wore a white wide-leg boiler jumpsuit.

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2018, MTV EMAs

In 2018, Jackson sported a mixed-plaid skirt over camouflage pants underneath a long black tweed jacket.

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2019, Rock & Roll Hall Of Fame Induction Ceremony

In 2019, Jackson was inducted into the Rock & Roll Hall of Fame wearing a black caped gown with feathers and long evening gloves.

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2020, Pre-GRAMMY Gala

Arriving to the 2020 Pre-Grammy Gala, Jackson wore a leather black utility trench coat with a matching leather headband.

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2020, Gatsby Gala

Channeling the Roaring ‘20s with pearls and a cloche hat for the Gatsby Gala in London.

See more style evolutions from Miley Cyrus, Nicki Minaj, and Ashanti.

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