From child star to solo pop superstar, Janet Jackson has lived through every season of fame – and her style story is just as iconic. Follow along as we take you through the highs, lows and inexplicable fashion moments of the one and only Ms. Jackson.
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Janet Jackson strikes a pose with big sister LaToya in 1977
Already a seasoned pro on the small screen, appearing alongside her siblings on the variety show The Jacksons in 1976, an 11-year old Janet Jackson, recently cast for a role on Good Times (which would catapult her into several other television roles), posed for a portrait session with older sister LaToya Jackson in 1977.
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Janet Jackson is a teen star on the rise at the American Music Awards in 1983
At 17 years old, Janet was just coming off the success of her debut album and enjoying her new position as Billboard’s highest-ranking female vocalist (based on the ranking of Year-End Black Album Artists). At the American Music Awards in 1983, Jackson stepped out in a bold red strapless gown with a tiered skirt. The look was on-trend for the times and reflected a playful style sense from the otherwise seemingly-shy star.
Related: Kylie Jenner’s style evolution.
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Janet Jacket lives for an oversized blazer in 1984
Nineteen-eighty-four was the year an 18-year-old Janet Jackson would elope with singer James DeBarge. The marriage wouldn’t last, but Jackson’s fondness for oversized, boxy blazers would hold strong throughout the 80’s.
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Janet Jackson takes control of her career in 1988
So late-80’s Janet Jackson may not be our favourite in terms of style choices, but this was the era where Jackson finally made real strides to distance herself from the Jackson Five – and all the family drama that came with it. Producing her third album with a new team in just six weeks, Control was released in 1986 to massive success – setting a theme for all her music to follow. Pictured here in 1988, Jackson looks cool, confident and very much in control. Stronger style choices with less of an emphasis on pop-queen gowns, instead a more utilitarian theme, was the vibe during this time.
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Janet Jackson is a picture-perfect 90’s style icon in 1992
Looking every bit the 90’s fashion icon, Jackson rocked a casual cool-girl outfit we’d be happy to wear today.
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Janet Jackson is the queen of crop tops in 1994
Attending a plaque presentation for 10 million copies sold of her album Janet in 1994, Jackson was a poster-child for 90’s trends. From the trashed baggy jeans to the crop top and half-up hair style, this was the look of the times, and no one did it better than Jackson – who might’ve also been going by Mrs. Elizondo Jr. (for her then-husband singer/dancer/director René Elizondo Jr.) were it not for the fact that the pair would keep the marriage under wraps until their split made the headlines in 1999.
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Janet Jackson is in full-Matrix mode at the MTV Movie Awards in 2000
After the soft styling of the 80’s and trendy looks of the 90’s, Jackson made the 2000’s her own with what would be an endless array of super bold and sexually-charged style choices. Finally taking hold of her celebrity, Jackson seemed determined to let her fashion freak-flag fly – and we’ve been here for it since day one.
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Janet Jackson shocks no one in a belly-baring crop top for the Vanity Fair Oscar Party in 2002
Sporting a barely-there crop top, belted low-rise jeans and long overcoat, Jackson was no doubt onboard the western-cowgirl trend of the times (Britney vibes, anyone?) While the look is definitely more cheesy than chic, who can deny those washboard abs – get it, Ms. Jackson!
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Janet Jackson and the “wardrobe malfunction” of the century at the Super Bowl in 2004
Listen, you just can’t talk about 2004 without talking about the infamous Super Bowl “wardrobe malfunction” between Jackson and Justin Timberlake. Whatever your take was on this moment, it was a “thing” for a long time – and here we are, giving it its due. Moving on now…
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Janet Jackson is sleek and stylish at the Billboard Music Awards n 2006
One of the best things about Jackson’s style is that the star is constantly serving up something new. She may have a few go-to favourites (crop tops and shoulder pads, anyone?) but the music industry icon is a master of reinvention. You never know what you’ll get when the legendary Ms. Jackson takes the red carpet.
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Janet Jackson is timeless at the Hollywood Film Festival’s Hollywood Awards in 2007
With no sequins or bared midriffs in sight, Jackson had onlookers doing a double take – for different reasons than usual – when she stepped out for an awards event in 2007. Jackson stunned in a simple black gown, minimal accessories and side-swept locks as she proved – without a doubt – that she had no trouble holding attention in even the most “muted” of fashion looks.
Related: Jennifer Aniston’s style evolution.
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Janet Jackson goes off-the-shoulder for a film preview screening in 2010
Fresh off her breakup with longtime boyfriend Jermaine Dupri, Jackson was all smiles in an airy, off-the-shoulder draped dress while attending a film screening in 2010. The dress may have missed the mark, but with that show-stopping smile, it’s hard to call this look a total loss.
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Janet Jackson stuns at an amfAR event in 2011
Attending amfAR's Cinema Against AIDS Gala in 2011, Jackson wowed in a satin top-and-skirt combo that still has us inspired.
Related: Selena Gomez’ style evolution.
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Janet Jackson is a vision in white at an amfAR event in 2012
Excuse us while we pick our jaws up off the floor, but this 2012 white gown moment still gives us all the feels. Attending the amfAR's Cinema Against AIDS Gala, Jackson wore a floor-length white gown that lives on as one of our favourite simple-statement looks from the star of all-time.
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Janet Jackson goes back to her (suit style) roots in 2013
Looking timeless at amfAR's 20th Annual Cinema Against AIDS in 2013, Janet Jackson reminded fans of her ability to rock a suit like no other. We – are – not – worthy!
Related: Harry Styles' style evolution.
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Janet Jackson throws it back at a tour after-party in 2017
For her State of the World Tour after-party look, Janet Jackson seemed to nod to her style roots with her 90’s inspired hair and early 2000’s leather-heavy outfit. The outfit was a lot and we’re wishing she had pulled back on all the (past and present) trends she worked into this one look.
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Janet Jackson does too much at the Billboard Music Awards in 2018
From the full skirt, to the belt, to the hair – we’re not sure where to start, and frankly, we’re still not sure how we feel about Jackson’s look for the 2018 Billboard Music Awards…
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Janet Jackson is inducted into the Rock & Roll Hall of Fame in 2019
OK so we know – we know – this look is a little much. But to be honest? We’re into it. It’s heavy on the moody-glam and it’s signature Janet Jackson – and for a moment like this one: being inducted into the Rock & Roll Hall of Fame – it was the right choice. OK, maybe not the gloves…
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Janet Jackson rocks a leather look for a pre-Grammy event in 2020
It’s a belted, biker-jacket-inspired, full-length leather gown, folks. And yes, Janet Jackson pulled it off.
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Janet Jackson is a Gatsby-inspired boss-babe in 2020
We love a costume party. Attending a Gatsby-themed gala in early 2020, Janet Jackson looked the part – and we’re making notes for Halloween 2021. While the singer’s musical career may have peaked in the 90’s, it’s been her style story in recent years that’s been the most interesting to watch. Bold, unapologetic and always playful – we’re never disappointed in what Janet brings to the red carpet.
Related: Lady Gaga’s style evolution.