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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 her most memorable outfits in recent years.

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.

PHOTOS: Janet Jackson’s Style Evolution 

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