At the 2025 NAACP Image Awards, Bailey’s older sister, Chloe Bailey, also attended the ceremony. Chloe wore a sculptural Gaurav Gupta gown featuring a sculpted bodice and a high-reaching chest extending beyond Bailey’s shoulders.

56th NAACP Image Awards: Chlöe’s “Black Butterfly,” Halle’s Hollywood Glam! The Bailey sisters brought major fashion slay and elegance. Don’t you just love it when sisters in music are also sisters in fashion? Chlöe and Halle Bailey turned the 56th NAACP Awards into their personal runway, serving elegance, confidence, and a whole lot of slay.

The 2025 NAACP Image Awards, held on Feb. 22 at the Pasadena Civic Auditorium and hosted by Dean Cole, honor Black entertainers who left an indelible impact on arts and culture in 2024. The Wayans family will be inducted into the NAACP Hall of Fame and former Vice President Kamala Harris will receive the Chairman’s Award.