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Discover Halle Bailey's Style Evolution [PHOTOS]

Allie Fasanella
6 min read
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Halle Bailey has transformed before our eyes into a full blown blockbuster movie star, but she got her start in the entertainment industry long before “The Little Mermaid” and “The Color Purple” launched her to worldwide fame. She and her sister Chloe were discovered by Beyoncé at a young age and made music as a duo for several years, also both starring on “Grown-ish” before eventually pursuing projects as individuals. Given her wunderkind status in Hollywood, it’s no surprise that Bailey has stepped out in a plethora of memorable outfits over the years. Take a look at her style journey here, dating back to 2013.

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Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a pink dress and gray peep-toe pumps at the Disney Kids Upfronts in 2013.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a blue dress with glittery sandals at the 45th NAACP Image Awards in 2014.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a printed top and matching sandlas with a white skirt and blazer at the 2014 Radio Disney Music Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing red high rise jeans with a pale pink blouse and platform sandals at the 2016 BET Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a striped top with ripped jeans and patchwork denim open-toe booties featuring a clear heel at the BET Awards in 2016.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a floral jumpsuit with feather-embellished pumps at the 2016 MTV Video Music Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a navy and white dress with black leather round-toe booties at Tory Burch’s NYFW show in September 2016.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a black and white top with distressed jeans and pointy black pumps at the 2016 Billboard Women in Music Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a shimmery silver dress with matching sandals at the 2017 Wearable Art Gala.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a red dress with multicolored boots at the 2017 BET Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a black butterfly-print jacket with ripped jeans and floral platform sandals at Jeremy Scott’s NYFW show in September 2017.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a fuzzy pink look with sandals at the 2017 Glamour Women of the Year Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a striped Louis Vuitton blazer look with bejeweled PVC mules at the “Star Wars: The Last Jedi” film premiere in 2017.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing a brown plaid double-breasted suit with a pink fanny pack belt and pointy nude heels at the premiere of “Grown-ish” in 2017.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a semi-sheer embellished black dress with asymmetrical black lace velvet booties at the “Black Panther” film premiere in 2018.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a shimmery bronze coatdress with yellow satin mules featuring crystal detailing at the premiere of “A Wrinkle in Time” in 2018.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing neon yellow booties with a navy dress and black sweater at the Opening Ceremony show at Disneyland in 2018.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a colorful printed jumpsuit with slinky black sandals and long black gloves at the MTV Movie and TV Awards in 2018.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a purple plaid skirt with black leather ankle booties at the 2018 BET Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing an orange tracksuit with skinny velvet sandals at an event in 2018.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle wearing a teal dress and white Nike high-tops in NYC in 2019.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a bold Versace look with black sandals at the 2019 Vanity Fair Oscar party.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a purple minidress with pale purple sneakers at the Freeform Summit in 2019.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing an orange minidress with strappy pink sandals at the 2019 50th Annual NAACP Image Awards.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a patterned dress with strappy black sandals at the 10th Annual DVF Awards in 2019.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (R) wearing a a gray dress with white sneakers at the premire of “The Sun Is Also A Star” in 2019.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearnig a burnt orange dress with glittery pink ankle-strap sandals at the Walt Disney Television 2019 Upfronts.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle (L) wearing a patchwork denim look with white sneakers at the season 3 premiere of “Stranger Things” on June 28.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing a semi-sheer gown and ruffled layer at the 2023 Met Gal celebrating “Karl Lagerfeld: A Line of Beauty” held at the Metropolitan Museum of Art on May 1, 2023 in New York.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing white pumps featuring a small cutout with patterned pants and a dark jacket at SiriusXM Hollywood Studio on May 4, 2023 in Los Angeles.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing an irididescent blue gown at the world premiere of Disney’s “The Little Mermaid” on May 08, 2023 in Hollywood, California.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing white mules with a skirt and top set and blazer at “Good Morning America” on May 18, 2023 in New York City.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing a silky light blue gown with embellishments at the Australian premiere of “The Little Mermaid” at State Theatre on May 22, 2023, in Sydney.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey (R) wearing black heeled sandals with black apparel at the Hollywood Unlocked Impact Awards held at The Beverly Hilton International Ballroom on June 27, 2023 in Beverly Hills, California.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey, pictured in the middle, wearing knee-high black boots to go with a black and white outfit at Gucci Ancora during Milan Fasion week on September 22, 2023 in Milan, Italy.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing black glittering slouchy boots with a feathery black jacket at the premiere of “Renaissance: A Film by Beyoncé” held in Los Angeles in 2023.
 

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing black platform heeled sandals at the Glamour Women of The Year Awards 2023 at One Marylebone on October 17, 2023 in London, England.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing platform heels with a sparkling dress made of a chainmail-like material at the 66th Annual GRAMMY Awards held at Crypto.com Arena on February 4, 2024 in Los Angeles, California.

Halle Bailey Style Evolution

Halle Bailey Style Evolution
Halle Bailey Style Evolution

Halle Bailey wearing red heeled sandals with a matching gown at the 2024 MTV Video Music Awards held at UBS Arena on September 11, 2024 in in Elmont, New York.

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