Side-by-side beauty details of the Bailey sisters at the 2026 Essence Black Women in Hollywood luncheon. On the left, Chloe features a sharp winged liner and floor-length braid; on the right, Halle showcases a soft bronze glow and a textured high-top updo.
You can always bet that whenever Chloe and Halle Bailey show up to an event, they come through looking like two distinct individuals who just happen to share a legendary bond. For the 19th Annual Essence Black Women in Hollywood awards, the sisters reminded us why they are a constant on our watchlists, offering two very different perspectives on red-carpet style.
The event, which took place on March 12th at the Fairmont Century Plaza in Los Angeles, is a cornerstone of the awards season calendar. Guided by the theme “Off Script,” this year’s luncheon was a dedicated space to honour Black women who are rewriting the Hollywood narrative—moving beyond traditional roles to claim creative control and ownership. With Marsai Martin hosting and icons like Kerry Washington and LaTanya Richardson Jackson being celebrated, the room was a collective of the industry’s most influential architects.
Chloe opted for a look that was all about bold architecture. She wore a structured, deep burgundy velvet corset featuring a sharp peplum that sat over a floor-length skirt. The skirt itself was a conversation starter—a fierce tiger print that contrasted against the vivid blue and yellow floral details on her bodice. To keep the focus on the silhouette, she wore an exceptionally long, sleek braid that reached the floor, finishing with a clean, bronzed beauty palette.
Chloe Bailey in a burgundy velvet and tiger-print corset gown by Harris Reed. Photo Credit: Chloe Bailey/Instagram
Halle, meanwhile, leaned into a more fluid and airy aesthetic, perhaps taking a short breather from the promo run for her romantic comedy, “You, Me & Tuscany.” She arrived in a moss-green pleated chiffon gown that felt light and grounded at the same time. The dress featured a high neck with a cold-shoulder cut and a thigh-high slit that moved as she walked. She let her natural texture take centre stage with a voluminous, curly updo, accessorised with gold platform sandals and subtle gold jewellery.
Halle Bailey in a moss-green pleated chiffon gown at the Fairmont Century Plaza. Photo Credit: Halle Bailey/Instagram
It was a refreshing reminder of their range; even without coordinating, they managed to claim their own space on the carpet while contributing to an afternoon defined by sisterhood and creative power.
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