No one should be surprised that only a few of the men and women attending the 2026 Actor Awards Sunday night embraced the requested sartorial theme, “Reimagining Hollywood Glamor from the 1920s and 1930s.” It’s a good idea and part of their partnership deer Magazine and Netflix, while also considering raising the event’s red carpet so it can rival the Met Gala in May. Unfortunately, there is a huge difference between the two evenings, one focused on industry and the other rooted in artistic statements for the museum. At an industry-focused actor’s awards ceremony, no one should be blamed for wearing what they prefer, regardless of the required dress code.
However, many have found ways to channel required contracts in subtle and subtle ways. From bias-cut dresses to double-breasted jumpsuits and tuxedos, female stars and fashion designers opted for Old Hollywood glamor without veering into flapper or gangster territory. After the 1920s and 1930s, other decades that similarly cemented the marriage of Hollywood films and high fashion were also evident, from the cool structure of the 1950s to the more relaxed and seductive 1970s. The result: a beautiful blend of decades and influences, focused more than anything else on a central idea of Hollywood glamor.
With that in mind, we’ve selected 10 stars who either accepted the task or went their own way, all with great results.
Jenna Ortega in Christian Cowan
Wednesday Star Jenna Ortega is no stranger to bold red carpet choices, so it’s no surprise that the details of her look exuded 1920s vibes, from the lingerie vibe of her bias-cut Christian Cowan gown to the delicate drape of a Mikimoto necklace and thigh-high stockings that channeled the decade while feeling equally modern.
Tyler James Williams in Sergio Hudson
All shades of red were popular at the Actors’ Awards, with the color also seen on Wunmi Mosaku at Louis Vuitton and Patricia Arquette at Rick Owens. But few men choose suits in a color other than black, which is why Tyler James Williams stood out beautifully in an apple red tuxedo jacket designed by Sergio Hudson. The cut and fit of the jacket, combined with very classic details in his shirt, pants and tie, resulted in a look that was very crisp and clean on Abbott Elementary star. Williams finished off his look with a Blancpain watch and Christian Louboutin shoes.
Demi Moore in Schiaparelli
Demi Moore Schiaparelli’s dress brings to mind the glamorous fashion seen in 1950s musicals such as… Funny face or How to marry a millionaire It undoubtedly created a wow moment when… Landman The star stepped onto the carpet. From creative director Daniel Rosebery’s Spring/Summer 2026 couture collection, the elegant black wool crepe dress featured a dramatic “cloud” of white tulle down its back, a design that required more than 700 hours of embroidery work. Moore paired the look with more than 95 carats of Harry Winston diamonds set in platinum, while her shoes were also designed by Schiaparelli.
Jacob Elordi in Bottega Veneta
From gangsters to bankers, pinstripe suits had already become popular clothing among men in the 1920s, so that may have been the inspiration for Bottega Veneta’s custom Jacob Elordi suit. Global brand ambassador since 2024 for the Italian brand Frankenstein and Wuthering Heights The star paired the suit with a cotton poplin shirt, tie and lace-up shoes, also from the brand.
Teyana Taylor in Thom Browne
Among the most stunning gowns of the night was this custom design by Thom Browne for Battle after battle Star Teyana Taylor. Designed to highlight the anatomical intarsia effect, the bodice was composed of more than 160 patterned grey, white and champagne pieces of silk and wool, and led to an embroidered tulle mermaid skirt decorated with 400,000 sequins and 175,000 beads. Taylor accessorized the dress with Tiffany & Co. jewelry, including the Jean Schlumberger Tiffany & Co. Leaves Necklace crafted in platinum and 18-karat yellow gold, accented with more than 47 carats of diamonds.
Rufus Sewell in Briony
Co-star L Diplomat She struck the right balance between formal and relaxed in this all-black look from Brioni, which consists of a wool-silk blend evening jacket with subtle paisley trim, a black cotton tuxedo shirt and black tuxedo trousers. On his lapel, a single jewel, Stephen Silver-designed Pagoda Jabot pin, is crafted from 18k yellow gold and platinum and highlights a vivid yellow diamond and white diamonds around a 5.74-carat portrait-cut Colombian emerald.
Rose Byrne in Chanel
the If I had legs I would kick you The nominee showed beautiful ease in this brown embroidered silk crepe dress, from Matthieu Blazy’s Métiers d’art 2026 collection for Chanel. Byrne’s Messika jewelry included Sirenetta cascading high jewelry earrings, while her silver evening shoes were designed by Gianvito Rossi.
Cornette died in Bal Zileri
In contrast to Sewell’s tuxedo, Matt Cornett’s navy jacket by Milan-based pal Zileri was also done in a subtle print, this time in feathers, with black tuxedo pants. Cornette finished off his look with a 40mm Omega De Ville Prestige watch.
Chase Infiniti at Louis Vuitton
Delicate beaded headpiece Battle after battle The Chase Infinity star’s outfit was undoubtedly a nod to the 1920s, while her dress looked quite modern. Both the headpiece and dress were custom-designed by Louis Vuitton, with the latter made from hand-woven plissé fabric. Infiniti finished off the look with a variety of jewelry by De Beers London, including Metamorphosis Spring Diamond Chandelier Earrings in 18-karat white and rose gold, accented with 9.96 carats of white diamonds.
Conor Storey in Saint Laurent
Fresh from a trip a red eye follows him Saturday Night Live hosting duties, Hot competition The star appeared shirtless at the Actor Awards in a double-breasted Prince of Wales wool jacket and cashmere flannel wide-leg trousers, both designed by Saint Laurent by Anthony Vaccarello. Story completed his look with jewelry and a Tiffany & Co. watch, including a Tiffany Victoria Mixed Cluster necklace made of platinum and diamonds.
