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.