Chloe and Halle Bailey stepped out for the 57th annual NAACP Image Awards in Los Angeles on Saturday night, dressed in sharp silhouettes courtesy of Christian Siriano and Stephane Rolland, respectively. While Chloe opted for Siriano’s most recent ready-to-wear, Halle dove into Rolland’s spring 2023 couture archive.

Chloe Bailey dressed in Christian Siriano at the 57th NAACP Image Awards.
Gilbert Flores/Variety
Priced at $5,800 online, Chloe’s floor-length floral burnout gown added an elegant edge to the feminine prowess on the carpet. The design featured a delicate, floral-embroidered mesh skirt and winged, off-the-shoulder sleeves. Instead of billowing out, the skirt tapered in, wrapping her legs and falling just above the silver toe of her shoes.
Meanwhile, the silhouette of Halle’s couture dress settled somewhere between an hourglass and a flower just starting to bloom. The bottom of the garment hugged her body, with white abstract pieces floating from her midsection to the floor. The top featured an inflated collar, which started at the neckline and extended over her ears.

Halle Bailey at the 57th NAACP Image Awards.
Gilbert Flores/Variety
Both sisters loaded up on jewelry. Where Halle donned half-moon skeleton earrings and a bare neck, Chloe clasped dainty diamonds and a spiral choker. And while Halle pinned her locs in a bun, Chloe let her caramel-colored hair down.
In the past, Chloe has partnered with stylist Jason Rembert, makeup artist Bella Mayven and hair architect Nicole Newland; however, she’s yet to credit the glam team behind her Saturday night look. WWD has reached out for confirmation.

Chloe Bailey
Earl Gibson III/Deadline
Halle’s longtime stylist, Byron Javar, whose A-list client list also includes Karen Pittman and Taraji P. Henson, helped craft her statement-making aesthetic, alongside makeup visionary Christiana Cassell and hair artist Tinisha Meeks.

Halle Bailey
Every year, the NAACP Image Awards celebrate Black excellence across film, television, music, podcasts and more. The 57th annual ceremony will open with host Deon Cole from inside the Pasadena Civic Auditorium. A few of the attendees already received awards at the NAACP Creative Honors, otherwise known as the pre-show, on Thursday. The winners included Quinta Brunson and Kerry Washington.






