Janet Jackson’s Style Evolution Throughout Her Career: Photos

Janet Jackson turned heads at the 1977 American Music Awards in a colorful dress adorned with tufts of tulle and a statement hat.

Even at 10 years old, Janet Jackson was a force to be reckoned with. 

In a YouTube video posted by an account named Moonwalker, Michael Jackson invited his younger sister onstage at the 1977 American Music Awards as part of a brief comedy bit while co-presenting alongside Fred Allen Berry and Lola Falana. 

On her brother’s cue, Jackson strutted onto the stage in a bright yellow and pink gown with bedazzled accents weaving across the front. The dress and matching hat also featured layers of tulle that added a textured dimension to the look. 

Although Jackson wasn’t given any lines, the laughter and clapping from the crowd showed that she stole the show. 

Jackson wore bright and eye-catching colors when she played Millicent “Penny” Gordon on “Good Times.”

Jackson’s first major Hollywood role was in 1977 when she was cast to play Millicent “Penny” Gordon on the beloved sitcom “Good Times.”

Jackson’s attire on the show mimicked the bold color palette prevalent throughout the 1970s, including in this portrait photo of the cast. Her dress, paired with knee-high socks and a matching bow, was definitely in step with the style of the time. 

In 2012, Jackson told Anderson Cooper that a “Good Times” wardrobe staffer suggested she bind her chest and a producer once said she was “too heavy.”

“I was getting dressed for the very first episode — now this is my first time away from my family,” Jackson said. “The wardrobe lady, while she was dressing me, said I had to put bandages around [my] chest.” 

“I immediately thought, as I am isn’t good enough,” she said. 

Jackson teased her fierce, tough side with a simple black T-shirt and jeans in the “Pleasure Principle” music video.

Jackson began to show different layers to her style repertoire in 1986 with her smash album, “Control.” 

The music video for “Pleasure Principle,” which won best choreography at the 1988 MTV Video Music Awards, featured Jackson dancing around an empty loft in a black T-shirt and black jeans that were cinched at the waist with a belt. 

While Jackson’s ensemble is simple, the attire alongside the song’s catchy lyrics and choreography have cemented the project in music history. 

Jackson solidified herself as a fashion icon by wearing the legendary “Rhythm Nation” outfit.

By 1989, Jackson had officially forged a successful path outside of her brothers’ accomplishments. The release of her fourth studio album, “Janet Jackson’s Rhythm Nation 1814,” catapulted her straight to the top. 

While the song received many accolades, it’s her military-style uniform featured in the “Rhythm Nation” music video that’s continued to transcend decades. The outfit included a cropped black jacket with 80s-style shoulder pads, silver buckles, a leather collar, and black pants paired with matching boots. 

Jackson finished the look off with a ponytail and a black baseball cap that had the phrase “1814.”  

Other artists have paid homage to Jackson’s outfit, including in 2014 when Beyonće, and her daughter Blue Ivy, channeled Michael Jackson and Janet Jackson for Halloween. Actor Joseph Gordon-Levitt also mimicked the outfit in 2015 when he performed on Paramount Network’s TV series “Lip Sync Battle.”

Janet Jackson punctuated her “Poetic Justice” era with long box braids and cinched light-wash jeans.

Jackson’s iconic box braids became a staple of her style in the early 1990s. Around that time, Jackson filmed and starred in the 1993 film “Poetic Justice” directed by the late John Singleton, alongside rapper Tupac Shakur, and Regina King. The movie also featured poetry by Maya Angelou. 

In the film, Jackson sported a black, long-sleeve shirt with a square neckline and a pair of light-wash jeans cinched with a belt. Her box braids were topped off with a black newsboy hat. 

Tanisha Ford, author of “Dressed in Dreams” and associate professor of Africana Studies and History at the University of Delaware, spoke to HelloBeautiful in 2019 about the significance of Jackson’s box braids for Black people. 

“When I think box braids, I think Janet Jackson’s character in poetic justice,” Ford told the outlet. “Box Braids have always been a part of the culture from as long as I can remember, some version of them … but when Janet Jackson wore them, it elevated those braids to a certain level of like Black girl glam that is still felt every day and around the way in ways that we all wanted them.”

Jackson was a vision of white at the Grammy Awards in 1993.

While still rocking the “Poetic Justice” box braids, Jackson attended the 35th Annual Grammy Awards that same year in a captivating all-white, double-breasted pantsuit.

She elevated the look by also wearing silver jewelry and a white headscarf to style her braids in a flowing updo.

Jackson’s textured outfit in the “Scream” music video later sold for big bucks.

In 1995, Jackson and her brother, Michael, attempted to dominate the music industry with their single, “Scream.” Jackson garnered attention for her shaggy tresses and dark makeup in the music video. 

The two wore matching black textured long sleeve shirts and black leather pants. 

Rolling Stone reported that the clothes fetched $125,000 as part of the “​​Iconic Treasures From the legendary Career and Life of Janet Jackson” sale with Julien’s Auctions in 2011. 

One of Jackson’s more eye-catching ensembles came after her sixth studio album, “The Velvet Rope,” in 1997.

Around the time she released her sixth studio album, “The Velvet Rope,” Jackson’s style did a 180° turn when she dyed her naturally dark hair orange. While performing at the Smash Hits Poll Winners’ Party at the London Arena, she styled her hair in a series of smaller ponytails to highlight the new color.

Jackson also donned a punk rock-inspired fit created out of what appears to be a sheer black top, a cut-up red bustier with small strings of jewelry hanging across the front, dark cargo pants, and chunky boots. 

The outfit was completed with a large gold necklace that acted as a pseudo collar. 

Jackson continued to play with her hairstyle while performing on “The Velvet Rope Tour.”

“The Velvet Rope Tour” lasted from 1998 to 1999 and visited audiences across the globe.

Jackson kept her fierce persona going by wearing a cropped double-breasted jacket with prominent sleeve cuffs, a striped waistcoat peeking out from underneath, and wide-leg pants.

Her dark bangs featured glimpses of red as a possible nod to her previous dye job.

Jackson looked straight out of “The Matrix” while on the red carpet in 2000.

Keanu Reeve’s performance as Neo in the 1999 film “The Matrix” was a pop-cultural phenomenon, so it’s no surprise celebrities dove into the futuristic, post-apocalyptic aesthetic that transfixed Hollywood at the time. 

Jackson’s red carpet outfit at the 2000 MTV Movie Awards may have been a small homage, as she wore a floor-length leather gown topped with a leather trench coat. 

During the event, Jackson presented Keanu Reeves with an award for best male performance for his work in the film. 

Jackson shined in gold and yellow hues when honored as an MTV Icon in 2001.

By 2001, Jackson had been in the entertainment industry for more than 20 years, prompting MTV to pay tribute to the international superstar. According to IMDb, Jackson was the inaugural “MTV Icon” honored at the network. 

Jackson was escorted onstage by André 3000 and Big Boi of Outkast while they sang a “Ms. Jackson” rendition of their hit song for the crowd. Jackson donned a shiny gold crop top and suede wide-leg pants adorned with flower designs and fringe. 

The event included several stars who covered Jackson’s classics, including Destiny’s Child, *NSYNC, Pink, Usher, and Mya. 

Jackson’s Super Bowl XXXVIII Halftime Show outfit is unforgettable.

In 2004, Jackson performed alongside a number of artists — including P. Diddy and Nelly — at the Super Bowl XXXVIII Halftime Show, which became one of the most infamous Super Bowl performances to date. 

When it came time to perform “Rhythm Nation,” Jackson appeared onstage in a black bustier decorated with small metal pieces woven throughout the fabric, wide pants, and boots. The ensemble was elevated with pops of red across Jackson’s chest and on her fingernails. 

At one point during the “Rock Your Body” duet with Justin Timberlake, he accidentally tore Jackson’s costume, which bared her breast on live TV.  Jackson, Timberlake, and MTV all released statements following the incident. 

Insider’s Kim Renfro previously reported on how the incident changed the trajectory of Jackson’s career following the backlash.

Jackson sported some ombré action while attending the Alexander McQueen boutique opening in 2008.

Jackson appeared in a Kimono-style dress with a pink to purple ombré transition at the boutique opening. 

Jackson later paid tribute to McQueen with her outfit at the “Why Did I Get Married Too” premiere red carpet in March 2010. He died by suicide in February of that year. 

“[McQueen was the] very first fashion show I ever went to. He invited me to his show in the late 1990s in London. I’ve always been a fan of his,” Jackson said, People reported. “True genius, and I’m not using the word loosely at all.” 

Jackson celebrated her brother, Michael, after his death in 2009 in a black and white ensemble that mirrored her previous outfits.

Michael Jackson died on June 25, 2009, at his Holmby Hills home in Los Angeles. Three months later, the MTV Music Video awards paid homage to him with a tribute show that showcased his most iconic songs. 

About halfway through the performance, Jackson appeared onstage to do a rendition of “Scream.” Jackson donned what looked to be a black and white leather top with large shoulder pads, metal accents, and pants. 

Jackson’s outfit resembled her Super Bowl costume with the extra leather fabric placed overtop the pants. 

Jackson’s hair reached new heights when she dazzled at the 2018 Black Girls Rock! Awards.

Jackson looked absolutely gorgeous when she walked across the Black Girls Rock! Awards show red carpet. 

She wore a dark blue ball gown adorned with black floral patterns and a sheer top to show some skin in a daring display. The dress featured a spiked body harness, and Jackson elevated her look by wearing her hair in a stretched top knot. 

Vogue reported that Christian Siriano designed the gown.