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Chlöe Bailey‘s dynamic voice and on-screen presence continue to elevate her multi-faceted career. Now that the 26-year-old is more comfortable in Hollywood, she’s spreading her style wings. Yesterday, Bailey debuted one of her edgiest outfits yet.

Wearing a gold bodysuit, Chloe Bailey performs on stage at the BET Awards
Chlöe Bailey performs onstage at the 2024 BET Awards | Paras Griffin/Getty Images for BET

On October 1, GLAMOUR honored Bailey with “Musician of the Year” at the publication’s annual Women of the Year Awards. In addition to a spot on the GLAMOUR UK cover, the former vegan discussed overcoming adversity and finding self-confidence with the magazine. Then, GLAMOUR fêted Bailey and the other winners at the star-studded awards ceremony in London.

Wearing a red trumpet-style dress, Chloe Bailey poses on the red carpet at the Glamour Women of the Year Awards 2024
Chlöe Bailey at the Glamour Women of The Year Awards 2024 | Alan Chapman/Dave Benett/Getty Images; Gareth Cattermole/Getty Image

Chlöe Bailey went Old Hollywood for the awards show, pinning her waves up in a voluminous updo atop her head. The “Have Mercy” singer curled a few strands to frame her face and wore winged eyeliner à la Marilyn Monroe. Channeling the Golden Age of Hollywood, Bailey wore a trumpet-style strapless Robert Wun couture dress in true red. She donned matching opera gloves and simple diamond earrings, showing off her décolletage.

Wearing a red trumpet-style dress, Chloe Bailey poses on the red carpet at the Glamour Women of the Year Awards 2024
Chlöe Bailey on October 01, 2024 in London | Mike Marsland/WireImage

The most titillating part of The Exorcism actor’s classic ensemble was the pointy chest area. The bust featured exaggerated seams where nipples would fall. Wun likely achieved this by exaggerating the darts to create an edgy accent for the traditional gown and gloves. Bailey loved the look, writing on Instagram, “I felt like a babydoll tonight. Thank you @glamouruk for naming me Woman of the Year’s Musician of the Year. I am incredibly honored and filled with such gratitude!!”

Wearing a red trumpet-style dress, Chlöe Bailey poses with rapper Eve on the red carpet at the Glamour Women of the Year Awards 2024
Chlöe Bailey and Eve at the Glamour Women Of The Year Awards 2024 | Karwai Tang/WireImage; Alan Chapman/Dave Benett/Getty Image

Bailey also thanked singer and rapper Eve for presenting “Musician of the Year” to her. When the Grown-ish star took to the stage to accept her award, she delivered a heartfelt speech. “As an honoree, it gives me such joy because I know that even if it’s just one girl or one young woman who sees this speech, it will make her realize that she can do anything that she wants to do.”

Three winners of the Glamour Women Of The Year Awards 2024 pose on the red carpet in formalwear
Jodie Turner-Smith, Simone Ashley, and Cally Jane Beech at the Glamour Women Of The Year Awards 2024 | 1st and 3rd images: Alan Chapman/Dave Benett/Getty Images; 2nd image: Karwai Tang/WireImage

In addition to Bailey’s “Musician of the Year,” several other stars received honors from GLAMOUR. Simone Ashley earned “Gamechanging Actor.” Cally Jane Beech won “Activist of the Year,” and Francesca Amewudah-Rivers received “Theatre Actor.” Jodie Turner-Smith earned “Screen Trailblazer.”

Three winners of the Glamour Women Of The Year Awards 2024 pose on the red carpet in formalwear
Pamela Anderson, Keely Hodgkinson, and Katherine Ryan at the Glamour Women Of The Year Awards 2024 on October 01, 2024 | 1st and 3rd images: Alan Chapman/Dave Benett/Getty Images; 2nd image: Mike Marsland/WireImage
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Katherine Ryan won “Feminist Hero.” Keely Hodgkinson earned “Sporting Hero,” and Jameela Jamil received “Gamechanging Voice.” Pamela Anderson won the “UK Impact Award.” Additionally, Samsung awarded the “Rising Star” award to three women this year: Maddie Haynes, Ysabelle Salvanera and Amelia Onuorah.