From the moment she hit the scene in the Grammy-nominated R&B group Chloe x Halle with sister Chlöe, it’s as if the world knew Halle Bailey was bound to take over. At just 23 years old, the soprano singer has managed to make a global impact on every industry she enters, from the group’s viral cover of Beyoncé’s “Pretty Hurts” to making history as the first Black woman to play Ariel in the live-action remake of Disney’s “The Little Mermaid.” Apart from conquering music with her sister, Bailey’s made quite the name for herself. She’s appeared on multiple magazine covers, from Ebony to Vogue, and successfully launched her solo career with the hit single “Angel.”
Bailey has also become one of fashion’s newest It girls and more than lives up to the hype. Boundary-pushing looks defined her early career, including the patterned jumpsuit and feathered nose piercing she wore for her first MTV Video Music Awards in 2016. She commanded attention at the same award show just five years later in a white cutout Mônot dress, cementing herself as a red carpet pro. Later that year, she had a Met Gala debut like no other, wearing a bubblegum-pink Rodarte bodysuit with fringe and a plunging V-neckline, a refreshing departure from the usual red carpet gowns seen on fashion’s biggest night.
In tandem with her professional evolution, the “Ungodly Hour” songstress has embraced an even more elevated aesthetic, taking sartorial cues from Chlöe and her role as Princess Ariel. Thanks to stylist Nichole Goodman, Bailey has enjoyed many groundbreaking style moments, including the Joanna Prazmo bra-and-skirt set for her 2022 Variety cover, a midnight-navy cutout Georges Hobeika gown for the Wearable Art Gala, and a teal Valdrin Sahiti dress for “The Little Mermaid”‘s world premiere. She continued her mermaidcore era with a pale-blue pearl gown from Georges Chakra’s spring 2004 collection, effortlessly nailing archival fashion.
Lately, she’s traded in her more skin-revealing pieces for designs that are more free-flowing than body conscious. She attended Gucci’s Ancora show during Milan Fashion Week in a roomy black coat, a white shirtdress, and leather boots from the luxury brand. For the Glamour Women of the Year Awards in London, she wore a Nicole + Felicia Couture minidress with a voluminous skirt featuring 3D roses.
As Bailey continues making her mark, scroll down memory lane to see her best looks.
Related: Chlöe and Halle Bailey on Their VS Pink Collab and Upcoming Third Album
Getty / Mike Marsland
Halle Bailey at the Glamour Women of the Year Awards, October 2023
Halle Bailey glowed at the Glamour Women of the Year Awards wearing a Nicola + Felicia minidress with a voluminous skirt featuring 3D roses.
Getty / Jacopo M. Raule
Halle Bailey at the Gucci Ancora Show During Milan Fashion Week, September 2023
For Gucci’s Ancora show during Milan Fashion Week, Bailey wore a black-and-white ensemble from the brand that featured a roomy black coat, a white shirtdress, and leather knee-high boots.
Getty / Jeff Spicer
Halle Bailey at "The Little Mermaid"'s UK Premiere, May 2023
The “Angel” singer wore a white Miss Sohee gown for the film’s London premiere. The heavenly ensemble featured delicate embroidery and a glittering headpiece.
Getty / Variety
Halle Bailey at "The Little Mermaid"'s World Premiere, May 2023
For the highly anticipated release of the movie, Bailey surely delivered in a metallic blue dress by Valdrin Sahiti that imitated the appearance of liquid. She accessorized with large diamond earrings and mermaid-inspired makeup to match.
Getty / Jamie McCarthy
Halle Bailey at the Met Gala, May 2023
For the 2023 Met Gala, Bailey wore a custom white Gucci ensemble that included a sparkling, sheer lace halter-neck gown and a dramatic ruffled cape.
Getty / Arnold Jerocki
Halle Bailey at the Gucci Afterparty During Milan Fashion Week, February 2023
En route to Gucci’s afterparty during Milan Fashion Week, Bailey gave us a chic yet edgy street style moment in a full ensemble from the fashion house. The look consisted of a black cropped corset top, a logo midi skirt, sparkly mules, and a neutral coat. She then accessorized with sleek shades and a black leather shoulder bag.
Getty / Kevin Mazur
Halle Bailey at the Oscars, March 2022
For her Oscars debut, she wore an alluring turquoise gown with an extreme cutout from Roberto Cavalli with heels to match.
Getty / Jerritt Clark
Halle Bailey and Chlöe at the Wearable Art Gala, October 2022
In a sweet sister moment at the 2022 Wearable Art Gala, Bailey wore a midnight-navy cutout Georges Hobeika gown that featured crystal-encrusted halter straps, shoulder and stomach cutouts, and stone-trimmed sleeves. She finished things off with Fernando Jorge’s disco ring and waterfall earrings from JustDesi. Meanwhile, Chlöe wore a pink, fucshia gown from Aje.
Getty / Kevin Mazur
Halle Bailey at the CFDA Fashion Awards, November 2022
At the 2022 CFDA Fashion Awards, the “Do It” singer sported a pink Carolina Herrera dress with an ab-baring cutout and high-leg slit. She completed the look with red heeled sandals, emerald earrings, and a yellow clutch.
Getty / Jeff Kravitz
Halle Bailey at the Met Gala, May 2021
Bailey turned heads at the 2021 Met Gala in a pink, fringed Rodarte jumpsuit with coordinating heels.
Getty / Nicholas Hunt
Halle Bailey and Chlöe at the VMAs, August 2018
For the 2018 MTV Video Music Awards, the Bailey sisters enjoyed a matching style moment in 3D printed gowns by Iris van Herpen.
