Janet Jackson has done it all — not only as one of the top bestselling artists and performers of all time, but her style remains as influential as ever, too.
Since the very beginning of her career in the late ‘60s as a child star, Jackson has had many definitive eras over the decades. But there was something about the ‘90s that truly formed her signature style and put her on the fashion map. Whether it was a power suit on the red carpet or her love of crop tops and baggy denim, the pop and R&B musician always served casual-meets-powerful style. Plus, she was all about the details that really made her outfits stand out, from a simple pair of sunglasses to her go-to statement buckle belt or an added hat or hair accessory to complete the full look.
Ahead, check out Janet Jackson’s best ‘90s fashion moments.
1990, Hollywood Walk of Fame
While showing off her newly added plaque on the Hollywood Walk of Fame, Jackson wore her signature all-black Rhythm Nation 1814 look.
1990, Billboard Music Awards
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.
1992, Soul Train Music Awards
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.
1992, IFP/West Independent Spirit Awards
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.
1993, Grammy Awards
During the 1993 Grammy Awards, the singer wore a white suit with a matching white headband and a diamond necklace.
1993, Hollywood Walk of Fame
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.
1993, Target Center
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.
1994, Oscar Awards
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.
1994, Janet Tour Afterparty
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.
1994, MTV Movie Awards
While on stage for the 1994 MTV Movie Awards, she wore a black-and-white striped crop top with black joggers and boots.
1994, MTV VMAs
During the 1994 MTV VMAs, the Janet star rocked baggy denim overalls with a black top and black shoes, paired with a logo cap.
1995, Janet Tour
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.
1995, MTV VMAs
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.
1997, The Velvet Rope Album Launch
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.
1997, The Velvet Rope Album Release Party
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.
1997, The Velvet Rope Album Release Party
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.
1997, MTV VMAs
Wearing a red short-sleeve button top with a black silk maxi dress and red sandals to the 1997 MTV VMAs.
1998, Blockbuster Awards
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.
1998, Janet Jackson Press Conference
During a press conference in 1998, the musician wore a striped blazer with matching pants.
1998, The Velvet Rope Party
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.
1999, Oscar Awards
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.
1999, Source Hip-Hop Music Awards
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.
1999, MTV VMAs
The singer ended the decade beside rapper Q-Tip, wearing a dark blue dress and a sparkly diamond necklace at the 1999 MTV VMAs.