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Janet Jackson’s fashion evolution from sexy siren to style icon: she showed off skin as a 90s sex symbol and married into Middle Eastern modesty, but these days she’s a front-row fashion week queen

Janet Jackson’s style has changed drastically over the years. Photos: @janetjackson/Instagram
Considering her early days as a child star and being part of one of the most famous families in the world, it’s fair to say Janet Jackson has grown up in the eternal glare of the public eye.
Janet Jackson with her brother, Michael Jackson. Photo: @janetjackson/Instagram

And much like our own family members, Jackson’s wardrobe has undergone some drastic changes over the years. But now, at age 56, the iconic singer seems to have found her passion for luxury brands, boldly experimenting with her image, becoming a fashion week front row regular, and most importantly … having fun.

Janet Jackson with Vogue’s editor in chief Anna Wintour. Photo: @janetjackson/Instagram

Here’s a closer look at Janet Jackson’s style evolution …

Sexy siren

Janet Jackson in 1993. Photo: @janetjackson/Instagram

Jackson started releasing music in the 80s, but it was undoubtedly the 90s when her career peaked with string of hit singles and successful albums.

Janet Jackson at New York’s Radio City Music Hall in this 1995 file photo. Photo: AP

While her music style changed over the decade, Jackson’s love for abs-flashing crop tops and baggy denims didn’t. Neither did her love for showing skin.

Janet Jackson sings during Thomas Gottschalk’s game show Bet It … !? in 2001. Photo: Reuters

From her sultry 1993 album cover right through to 2008’s Discipline era, Jackson was not afraid to embrace her sexuality.

Janet Jackson poses for photographers after she presented an award during the 2nd Annual BET Awards in 2002, in Los Angeles. Photo: AP
In fact, she appeared close to nude on most of her album covers during the 90s and noughties, and was infamously “cancelled” after her breast was exposed during the Superbowl in 2004.
Singer Janet Jackson (L) covers her right breast with her hand after it was exposed during the halftime show at Super Bowl XXXVIII in Houston, Texas Sunday in February 2004, next to Justin Timberlake. Photo: EPA

Her accidental exposure almost cost her career, as major TV networks and media outlets blacklisted the star, per numerous sources.

Middle Eastern modesty

Janet Jackson and Wissam Al Mana. Photo: Handout

But as the noughties came to an end, so did Jackson’s revealing wardrobe.

When Jackson quietly started dating Qatari billionaire Wissam Al Mana, now 48, in 2010, her style understandably became more conservative.

The couple eventually married in 2012 and moved to the Middle East, where Jackson almost completely disappeared from public eye, apart from attending a few high profile fashion events.

Her style largely adhered to local and religious standards, and she was often seen wearing abayas. She was even spotted shopping for the traditional Arabic garment in Dubai’s Jumeirah Road in 2013.

Janet Jackson at a Vogue event held at The Dubai Mall. Photo: Getty Images

When Jackson eventually made a rare public appearance at a Vogue event in Dubai in 2014, she covered up in a long-sleeved black dress with high neckline.

Janet Jackson’s Unbreakable tour. Photo: YouTube
Not surprisingly, when Jackson finally made her musical comeback a few years later on 2015’s number one album Unbreakable, her lyrics were less explicit and her style more understated.
Janet Jackson’s style choices for her Unbreakable tour was more conservative compared to her previous looks. Photo: YouTube

While on tour for the album, Jackson was styled by designer Kim Bowen for the show, along with custom-made wedge trainers by Giuseppe Zanotti, but the show only featured only two demure costume changes – a far cry from the many outrageous costume changes on previous tours.

However, the tour was not meant to last and was cut short when Jackson and Al Mana announced they were starting a family.

Janet Jackson with her son, Eissa Al Mana. Photo: @janetjackson/Instagram
The couple eventually welcomed their son Eissa in January 2017, when Jackson was 50. However, just three months later, they shocked fans when they announced their split, reported People.

Rise of the style queen

Janet Jackson with designer Alexander Wang. Photo: @janetjackson/Instagram

So what’s a newly single mother in her fifties to do? Only rise like a stylish phoenix from the ashes of luxury, of course.

When Jackson returned to the stage later that year for her State of the World Tour, she could’ve opted to return to her old sex siren persona, but instead continued to embrace her love for luxury fashion and her understated style.

 

Stylist and costume designer Robert Behar revealed how Jackson was involved in the entire creative styling process of the tour.

“Her inspiration and knowledge of what she wants to do is so great and she’s there for every single one of the dancers’ fittings,” Behar told Billboard Style. “She’s very hands on but in a kind and generous way, so it’s amazing to work with her.”

Of course, all outfits on the tour were custom made.

 

“We participated for one segment with Fear of God designer Jerry [Lorenzo]. He did a whole section which was really a lot of fun. Christian Louboutin and Rick Owens did Janet’s shoes, and the Louboutin denim boots she wears at the end [of the show] were made especially for her,” Behar revealed during the interview.

Luxury goddess

Janet Jackson wearing Valentino. Photo: @janetjackson/Instagram

In more recent years, and particularly post pandemic, Jackson’s love for luxury brands and designers has become increasingly evident. After keeping out of the public eye for most part of the last decade, fans were instead treated to “High Fashion Janet Jackson”, who has become a regular on the Fashion Week front-row circuit.

Janet Jackson wearing Alexander McQueen. Photo: @janetjackson/Instagram
Jackson stole the show when she attended designer Thom Browne’s show at New York Fashion Week last year.
Janet Jackson sitting with Anna Wintour at Thom Browne’s New York Fashion Week show. Photo: @janetjackson/Instagram

Her look was seen as an ode to her ability to break boundaries, as she mixed traditional gender outfits with her own feminine touch.

 

Jackson turned heads again when she showed up at the Rock & Rock Hall of Fame induction ceremony in November 2022.

Janet Jackson at the Rock & Rock Hall of Fame induction ceremony in November 2022. Photo: @janetjackson/Instagram

Her black high neckline silk number, buttoned bodice and pointed collar was a modern nod to her 80s “Control” era.

Control album, 1986. Photo: Handout

Her simple but elegant look was complimented with a bold hairdo that made her the centre of attention.

Janet Jackson, Ramla Ali and Letitia Wright attend the Alexander McQueen SS23 womenswear show at the Old Royal Naval College in October 2022, in Greenwich, England. Photo: Getty Images

The songstress proved she might be more understated these days but isn’t afraid to show some skin again, when she attended the Christian Siriano spring 2023 fashion show.

Janet Jackson with Christian Siriano. Photo: @janetjackson/Instagram

Wearing an all-black outfit, with a revealing sheer top, black bra and maxi skirt, it was seeing a glimpse of the old Jackson we knew, but with a lot more style.

Janet Jackson wearing Christian Siriano. Photo: @janetjackson/Instagram

Not surprisingly, Jackson was honoured by Harlem’s Front Row and LVMH with the Icon of the Year award at New York Fashion Week in 2022.

Janet Jackson was dressed by Wouri Vice. Photo: @janetjackson/Instagram
She was dressed by Wouri Vice in an off-white FW22, the late Virgil Abloh’s last collection for the brand.
 

As the iconic singer plans to embark on her Together Again tour in April with a rumoured new album in the pipeline, we look forward to seeing where her fashion journey takes her next.

Lea Seydoux, left, and Janet Jackson attend the Louis Vuitton ready-to-wear spring/summer 2023 fashion collection presented in October 2022, in Paris. Photo: AP

All eyes on you, Ms Jackson …

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  • Janet Jackson’s earlier looks were bold, fun and showed plenty of skin, but that all changed after motherhood and marriage to Qatari billionaire Wissam Al Mana
  • Since divorce and a musical comeback, the pop sensation has re-emerged as a bona fide fashion maven, with a penchant for luxury labels and understated chic