Up until the Resonator Awards on January 27, fans weren't sure if Olivia Rodrigo would make an appearance at the 2026 Grammy Awards. (The pre-Grammys soirée tends to tease Sunday's guest list.) Since she's not nominated this year, the three-time winner could've watched the ceremony from her couch like the rest of us. Still, we got our hopes up—and, alas, Rodrigo did indeed skip the 2026 Grammys.
This year would've marked the singer's fifth Grammys, plus her fifth with styling sisters Chloe and Chenelle Delgadillo. She gave us plenty of looks over the weekend, though, at pretty much every major pre-Grammys event. On Jan. 27, the Delgadillo duo dressed her in a Valentino drop-waist Georgette Dress from the brand's Resort 2026 collection for the Resonator Awards. Three rows of black cascading bows decorated the mini's ruched, powder pink silk.
Livies hoped the four-figure pick was confirmation she'd wear Valentino at the 2026 Grammys, especially since the days-old Spring 2026 Couture collection—in all its vaudevillian, showgirl glory—was ripe for the taking.
On Grammys eve, Rodrigo was out again at Lucian Grainge's Universal Artist Showcase. She accepted the Amplifier Award in a vintage Miu Miu mini. Major kudos to the Delgadillos for tracking down the metallic gold, liquid organza dress, and extra points for Rodrigo for her "ICE Out" pin. Similar styles appeared on many red carpet looks at the 2026 Grammys.
The Delgadillo sisters first collaborated with Rodrigo in 2021, just in time for her first ever Grammys appearance in 2022. As far as debuts go, hers left quite an impression: She accepted three trophies in a skintight, off-the-shoulder gown from Vivienne Westwood. Pale pink graffiti-like trim emphasized its corseted silhouette; opera gloves and Swarovski chokers added a whiff of '90s nostalgia.
The next year, Rodrigo put on her presenter hat, as well as a more modest red carpet look. The "drivers license" singer looked classically cool in a dreamy little black Miu Miu dress. Semi-sheer panels atop its waist and skirt added just enough visual interest without stealing the show. To finish, Rodrigo traded diamonds for the cord necklace trend. (Jennifer Lawrence and the runway circuit wouldn't follow her lead until two years later.)
Chloe and Chenelle outdid themselves at the 2024 Grammys, when Rodrigo was up for six awards for Guts. She ended up on best-dressed lists galore for her archival Versace pull: a white Spring 1995 gown, stitched with red beadwork from top to bottom. It was originally modeled by Linda Evangelista, walking the runway eight years before Rodrigo was born.
Rodrigo's vintage Versace series continued at the 2025 Grammys with a cutout-heavy gown from the Spring 2000 collection. On the runway, it appeared in hot pink, but in black, the halter-neck slip read more timeless than overtly Y2K. Nearly $140,000 worth of Tiffany & Co. sparklers—all from the Victoria line—elevated the whole ensemble.
At just 22 years old (she turns 23 later this month), Rodrigo has already amassed an impressive Grammys style streak. If fans' suspicions prove correct and she is indeed teasing her third studio album, maybe we can look forward to a red carpet return in 2027.
