Janet Jackson’s Style Evolution Through the Years Includes Height-Defying, Dramatic & Iconic Fashion Moments

Janet Jackson is known for being the ultimate multi-hyphenate, but she’s also an outstanding entertainer and style icon. The Grammy Award-winning singer and songwriter has continuously set trends and influenced pop culture throughout the course of her career. From performances to red carpet appearances, Jackson has remained a fashionable force.

The pop icon has served up an immersive amount of style inspiration over the years. Her looks have included sheer designs, shiny puffer coat and dramatic eye-catching details. She is undeniably a master at monochromatic moments and always takes up her looks up a notch with various height-defying shoe styles.

Ahead of her Together Again World Tour, which kicks off in April 2023, here we take a look at Jackson’s most memorable outfits in recent years.

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Janet Jackson, Harlem's Fashion Row Show And Style Awards, New York Fashion Week
Janet Jackson attends Harlem’s Fashion Row 15th Anniversary Fashion Show And Style Awards After Party on Sept. 6, 2022 in New York City.
CREDIT: Getty Images

Janet Jackson accepted the Icon of the Year award at Harlem’s Fashion Row 15th anniversary Fashion Show and Style Awards. The musician wore a full ensemble by Off-White. Her outfit consisted of a cropped blazer jacket, which she paired with graphic red and navy blue T-shirt. Giving her outfit a burst of drama was a beige tulle skirt, featuring flared tiered layers. Completing the star’s outfit, styled by Wouri Vice was a stack of sculptural Dinosaur Designs bangles and oblong Jennifer Fisher hoop earrings.

Janet Jackson, Gatsby Gala 2020, Celebrity Style
Janet Jackson attends the Gatsby Gala 2020 at Bloomsbury Ballroom on Jan. 30, 2020 in London, England.
CREDIT: Getty Images

Jackson stepped out in a ’60s-inspired ensemble for the 2020 Gatsby Gala in London. The dancer was dressed in all-black attire. She wore a fuzzy coat with a floor-length velvet gown. To amp up her look, she accessorized with long pearl necklaces, a black hat and sheer gloves.

Janet Jackson, Platform Sneakers, Metamorphosis afterparty
Janet Jackson attends her residency debut “Metamorphosis” after party at On The Record Speakeasy and Club at Park MGM on May 17, 2019 in Las Vegas.
CREDIT: Getty Images for Park MGM

Jackson was casual-chic while attending her residency debut “Metamorphosis” afterparty in 2019. The “Poetic Justice” actress donned a camouflage jumpsuit. She gave her wardrobe a boost with platform sneakers that featured a black and white checkered outsole.

Janet Jackson, Mnet Music Awards, Platform Oxfords
Janet Jackson attends the 2018 Mnet Music Awards in Hong Kong at AsiaWorld–Expo on Dec. 14, 2018 in Hong Kong.
CREDIT: Getty Images

In 2018, Jackson attended the Mnet Music Awards in Hong Kong. She mastered monochromatic styling by stepping out in a structured blazer and a dramatic ruffled sheer skirt. To take things up a notch, she added a sequin button-down shirt and platform oxfords.

Janet Jackson, Black Girls Rock!, Dress
Janet Jackson attends the Black Girls Rock! at New Jersey Performing Arts Center on Aug. 26, 2018 in Newark, New Jersey.
CREDIT: Getty Images

Jackson was a show-stopper while attending the Black Girls Rock! event in 2018. The “All For You” songstress arrived in a navy blue floor-length gown. The garment featured a high spiked turtleneck and sheer sleeves that was decorated with large flowers allover. The bottom of the piece included a wide skirt that was adorned with sequin flowers and had a ruffled hemline.

Janet Jackson, Ankle Boots, OUT Magazine
Janet Jackson attends OUT Magazine #OUT100 Event presented by Lexus at the Altman Building on Nov. 9, 2017 in New York City.
CREDIT: Bryan Bedder

In 2017, Jackson turned OUT Magazine’s #OUT100 event into an all-black affair. The chart-topping entertainer donned a short-sleeve fuzzy overcoat, which she paired with a fitted jumpsuit. The one-piece garment also featured a high-waist wrap skirt and long, dramatic sash at the back. Jackson completed her look with suede opera gloves and chunky platform ankle boots.

Janet Jackson, Source Hip-Hop Music Awards, Red Carpet, Platform Boots
Janet Jackson attends the Source Hip-Hop Music Awards on August 18, 1999 at the Pantages Theatre in Hollywood, Calif.
CREDIT: Ron Galella Collection via Getty

Jackson brought sleek style to the 1999 Source Hip-Hop Music Awards. She arrived wearing a 3/4 sleeve black dress that featured two front slits near the hem. The piece was held together by a corset that had gold and purple accents. To elevate her ensemble, she slipped into a set of platform boots.

Janet Jackson, 1998 VH1 Fashion Awards, Chunky Heels
Janet Jackson attends the 1998 VH1 Fashion Awards at Madison Square Garden in New York City.
CREDIT: WireImage

Jackson made an edgy style statement at the 1998 VH1 Fashion Awards. For the ceremony, she wore a cropped leather jacket with a bralette and baggy low-rise pleated trousers. On her feet was a pair of chunky leather shoes.

Janet Jackson, The Velvet Rope Album Release Party, Platform Boots
Janet Jackson attends “The Velvet Rope” album release party on September 9, 1997 at Sony Pictures Studios in Culver City, Calif.
CREDIT: WireImage

Jackson mastered Y2K style at her “The Velvet Rope” album release party in September 1997 in Culver City, Calif. The songwriter wore a see-through cutout top, which was layered over a black bralette. Jackson completed her look with baggy olive green cargo pants that were held up by a wide belt. She complemented the look with a silver choker necklace and styled her ginger hair curly. For footwear, she slipped into a pair of platform boots.

Janet Jackson, MTV Video Music Awards, Red Carpet, Platform Boots
Janet Jackson attends the 1994 MTV Video Music Awards at Radio City Music Hall in New York City.
CREDIT: FilmMagic

Jackson gave her sporty style an edgy upgrade for the 1994 MTV Video Music Awards. She wore a simple black top with baggy light-wash overalls. Her hair was styled in knotless braids and covered with a black dad hat. The pop artist’s look was boosted with a shiny pair of platform shoes.

Janet Jackson, American Music Awards 1987, Red Carpet, Pumps
Janet Jackson attends the 14th Annual American Music Awards on January 26, 1987 at the Shrine Auditorium in Los Angeles.
CREDIT: Ron Galella Collection via Getty

In 1987, Jackson gave a monochromatic style moment a sharp finish for the 14th annual American Music Awards. The “Why Did I Get Married” star was dressed in all-black attire that included a loose-fitting jacket and coordinating trousers. She completed the outfit with leather opera gloves and a spike heel pumps.

PHOTOS: Janet Jackson’s Style Evolution 

About the Author:

Ashley Rushford is the Digital Editor for Footwear News. She writes and edits stories about celebrity style, the latest fashion trends, shoe releases and exclusive interviews. Ashley received her Bachelor’s Degree in Journalism and Media Studies from Rutgers University and has written for publications like Essence Magazine and Black Enterprise.

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