Janet Jackson’s Best ‘90s Fashion Moments

At the start of the decade, the singer performed at the Met Center in Minnesota, wearing a black bralette with a white button-down top tucked into black pants.

While showing off her newly added plaque on the Hollywood Walk of Fame, Jackson wore her signature all-black Rhythm Nation 1814 look.

At the very first annual Billboard Music Awards, Jackson donned a black underwire bralette and a cropped blazer. She also wore leather pants and a chunky western-inspired buckle belt and silver hoops.

At the 1992 Soul Train Music Awards, the songstress wore a white short-sleeve top paired with a long black skirt. She then accessorized with large gold hoops and a black beret.

Janet Jackson attended the 1992 IFP/West Independent Spirit Awards wearing a black long-sleeve top tucked into baggy denim jeans and black leather boots. She also wore her go-to buckle belt and a beret.

During the 1993 Grammy Awards, the singer wore a white suit with a matching white headband and a diamond necklace.

Standing between producers Jimmy Jam and Terrence Lewis at the Hollywood Walk of Fame, Janet wore a black sweater vest with embroidered patches and a white button-down. She completed her look with black pants, shiny leather boots, black frames, and a hat.

Back in 1993, Jackson performed in Minnesota wearing a leather bralette under a plaid flannel paired with denim jeans, a buckle belt, and a scarf.

At the 1994 Oscar Awards, Jackson was spotted with her then-husband René Elizondo wearing an all-white look, including a white oversized blazer with loose-fitted pants, a diamond necklace, and a white shoulder bag.

While celebrating her sold-out concert tour for the Janet album, the singer wore a cropped black turtleneck with distressed jeans and a black leather bag.

While on stage for the 1994 MTV Movie Awards, she wore a black-and-white striped crop top with black joggers and boots.

During the 1994 MTV VMAs, the Janet star rocked baggy denim overalls with a black top and black shoes, paired with a logo cap.

During her sold-out tour in London back in 1995, the musician performed on stage in her coveted “If” outfit, which included a cropped embellished jacket and white top, along with high-waisted bottoms, thigh-high snakeskin boots, and an elaborate belt.

In 1995, the singer attended the MTV VMAs sporting a white cropped varsity top with the word “Pervert” on the back, following Michael Jackson’s child molestation allegations at the time. She paired her look with black trousers.

At the launch of her new album The Velvet Rope in 1997, the R&B queen wore an oversized leather jacket with a green dress. She accessorized with gold hoops and a blinged-out necklace.

During her album release party for The Velvet Rope, Jackson wore a black macramé top with a black bra underneath with cargo pants and platform boots.

She was also seen at the album’s release party with supermodel Naomi Campbell and singer Lisa Marie Presley wearing a gray blazer and a silk black dress.

Wearing a red short-sleeve button top with a black silk maxi dress and red sandals to the 1997 MTV VMAs.

Jackson attended the 1998 Blockbuster Awards in a black cropped fuzzy cardigan and a bralette peeking from underneath, along with a pair of khaki cargo pants and a black belt.

During a press conference in 1998, the musician wore a striped blazer with matching pants.

Jackson was seen alongside Chris Rock in a gray cropped sweater tank with black pants. She also paired her look with her signature belt and a black South Park embroidered cap.

Jackson is definitely a fan of the midriff trend, as she was seen in a cropped long sleeve top with an elaborate skirt and a diamond V-shaped necklace back in 1999 at the Oscars.

At the 1999 Source Hip-Hop Music Awards, the singer attended the red carpet event wearing a black maxi dress with a yellow iridescent corset.

The singer ended the decade beside rapper Q-Tip, wearing a dark blue dress and a sparkly diamond necklace at the 1999 MTV VMAs.