Janet Jackson’s Style Evolution, From Child Actress to Iconic Pop Star

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

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.

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

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.

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.

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

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

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

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

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

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

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.

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

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

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

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

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.

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.

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

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

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

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

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.

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

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.

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

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

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

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

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

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

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

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