Janet Jackson's Stunning Style Transformation

If you're someone of a certain age, there's a good chance you've never known life without Janet Jackson. Even if you're not a fan of her music and acting roles, like her brother Michael, Jackson has solidified herself as a pop culture icon, and her influence stretches deep and far. After all, Britney Spears, who's also had her own style transformation, wouldn't be the pop star she is without her love and admiration for Jackson.

Although it was music that made Jackson famous on an international level, her career started in 1976 with the premiere of "The Jacksons," a variety show that starred her and her siblings. Just one year later, when she was only 11, Jackson was cast in the television series "Good Times" as a main character for the final two seasons. While the role would officially launch her acting career, in 1982, Jackson's father, Joe — who was by most accounts a tyrant — scored Jackson her first record deal.

Since then, Jackson has released 11 albums (her most recent in 2015), had 10 acting roles, toured the world many times over, and had two residencies in Las Vegas. While her life has had some controversies, including an infamous wardrobe malfunction that she handled with grace during the 2004 Super Bowl halftime show, Jackson is someone who has always been able to find her footing again and bounce back. She's also done it with her own sense of fashion and style every step of the way, refusing to play by the entertainment industry's rules. Jackson's transformation has been, to say the least, stunning.

In 1977, Janet Jackson posed for a series of photos while sitting on a couch and wearing a Micky Mouse shirt. Just 11 at the time, Jackson paired the shirt with jeans and had her hair pulled back. She was absolutely adorable, already radiating with the type of star quality you don't see every day. Jackson had no idea what was to come or that in time she would become an internationally known pop star and one of the celebs who owned their success after Hollywood tried to tear them down. Hollywood has always been a brutal and unfair place for women, but Jackson was built to prevail.

Although MTV had already launched in August of 1981, giving musicians the opportunity to make videos to accompany their songs, American Bandstand was still around and allowed pop stars to show off their talent. In October 1982, Janet Jackson followed in the footsteps of musical heavyweights like The Beach Boys and Pink Floyd when she took the stage to perform a song from her debut album, "Janet Jackson." For the appearance, Jackson was the epitome of the early 1980s in her black graphic shirt and black jeans that she wore adorned with handkerchiefs and what looked like random pieces of faux fur. Talk about a decade that would ultimately date everyone.

If there's one thing that we can take from photos of people in the 1980s, it's that snaps were all the rage. We can also deduce that sharp lines and big shoulders, especially when paired with snaps, basically made the person rocking them a total fashion icon in the making. That being said, we can't be surprised that Janet Jackson would wear this ensemble for a 1985 photo shoot. To complete this overall look, Jackson opted for stone-washed jeans and one of the iconic hairstyles only Gen X remembers wearing: the mullet. Jackson is also serving up major Michael Jackson vibes here, too.

With the release of her third album, "Control," Janet Jackson became a bona fide pop star — and dressed like it. At the 14th Annual American Music Awards in 1987, where Jackson also performed, the artist wore black pants, a black fitted blazer, and just a pop of color from her shirt. For the next few years, black would be Jackson's go-to color for public appearances, especially during the release of 1989's "Rhythm Nation 1814," when she militarized the color. "Hoards of teen girls were imitating her distinctive look — black quasi-military long jackets, black tight-tight pants, and big white shirts," Ebony Magazine reported at the time (via Fandom).

By the time the early 1990s rolled around, Janet Jackson had done a complete 180 with her look. Long gone were the military outfits and the head-to-toe black ensembles. Instead, Jackson softened everything about her appearance, turning to baggy jeans and flannels — very much in style at the time — and embracing her free-flowing curls. This major style change coincided with her fifth album, 1993's "Janet," and film debut in "Poetic Justice," as she briefly went back to her acting roots. 

As many did at some point in the 1990s, Janet Jackson had a red hair era. In 1997, Jackson debuted the look — with a gorgeous curly lob — at the 1997 MTV Video Music Awards in New York City. Jackson completed the very 1990s hairstyle with a red velvet top — a popular fabric in the 1990s — and a long black skirt. Although her red hair era was short-lived, there's a good chance she probably inspired legions of fans to dye their hair red in a way that worked for any vibe.

Although there's no word on whether the 2005 EMI Post Grammy Awards Party had a theme, Janet Jackson is definitely channeling Bonnie Parker, of Bonnie and Clyde fame, with this fantastic outfit. The fitted black and white striped top is the perfect complement for the black tea-length skirt that has a bit of a ruffle at the hem. In proving that every detail was covered with this look, the black and white heels bring the stripe theme all the way to the floor. Jackson completed the ensemble with a black beret and a collection of silver necklaces, proving she's an absolute necklace layering pro.

Let's just say what everyone is thinking: Janet Jackson completely hit it out of the park when she attended amfAR's Cinema Against AIDS Gala during the 64th Annual Cannes Film Festival in 2011. Jackson was stunning in this sophisticated and elegant look from Haider Ackermann's fall 2011 collection, marking a major shift in her personal style. Although Jackson always dressed appropriately for the decade she was in, staying on top of trends, this outfit went beyond that. It said that Jackson was feeling comfortable in her skin and had made it through the other side after losing her brother, Michael, just two years before, at the very young age of 50.

In December 2019, Janet Jackson (here with Anna Wintour) attended The Fashion Awards in London for the first time to present an award to fellow fashionista Rihanna. For the event, Jackson was decked out in head-to-toe Stella McCartney, including a faux fur coat she wore for her arrival. As we saw in 2011, when Jackson was 45, age and maturity seemed to have played a role in how she approached fashion. In fact, Jackson was pulling off quiet luxury so well here that it was almost making Wintour, who was wearing Chanel, look a little frumpy. (Sorry, Anna!)

When Janet Jackson attended the Dancers Against Cancer's 2025 Gala Of The Stars in October 2025, jaws hit the floor. While she may not hit the red carpet that much these days, Jackson absolutely slayed in this black satin mini dress — with a train! — by Tom Ford, completing the elegant look with chic knee-high Christian Louboutin boots. Jackson, who showed off a dark blond wavy lob and a fresh face of barely-there makeup, was in attendance to receive the Icon Award for her impact on the entertainment industry as well as her philanthropy. It was a well-deserved recognition for a woman who has given so much, both artistically and otherwise, to our cultural landscape.