Star stylist Sam Woolf has been working with Latto only since November, but what a thrilling few months it’s been. Since releasing her second studio album, 777, last March, the best new artist nominee at Sunday’s 2023 Grammys has been riding a wave that could be dubbed “Big Energy,” to borrow from 777‘s hit single, which spent 37 consecutive weeks in the top 40 of the Billboard Hot 100 chart.

“Her record blew up globally and really put her on the map, but she’s still the same easygoing person, so open to ideas and fun to work with,” Woolf says of the Atlanta-born artist, whose real name is Alyssa Michelle Stephens. “For the Grammys, she said she wanted simply to feel really pretty and beautiful. We know pretty could mean a lot of things: princess, sexy, avant-garde. But we already did a more avant-garde look for the [American Music Awards], so we’re going in a different direction for the Grammys.”

At that November event, Latto wore a much-discussed black silk corset and veil, by London-based designer Dilara Findikoglu.

For the 2023 Grammys, Woolf reached out in December to designer Peter Dundas, who created roughly 10 sketches for consideration. The gown Latto ultimately chose is crafted a blush pink draped silk-chiffon gown and takes its cue from an iconic inspiration.

“We did a party together for New York Fashion Week last year, and I found her to just be the sweetest girl,” Dundas told The Hollywood Reporter Sunday afternoon. “She reminded me a bit of Marilyn Monroe in a way, that mix of someone who’s very sure of herself while also conveying this innocent air that’s totally charming.”

Dundas says he had Monroe in mind while sketching the gown Latto ultimately chose. “I took that idea of classic ’50s dresses, the sexy gowns that William Travilla created for Monroe, but I did it in my style, with cutouts and completely unconstructed,” he explains. “The silk chiffon is entirely hand-beaded, with thousands of bugle beads all over to create a subtle shimmer. The actual embroidery took two weeks to complete, and then a week in the couture atelier to put the dress together.”

Woolf also points to the era of 1990s supermodels as inspiration. “The look has a bit of that Claudia Schiffer, Cindy Crawford vibe about it as well,” he says. “It’s feminine, sexy, youthful and definitely bombshell.”

Two fittings on the Thursday and Saturday before the 2023 Grammys were key, Dundas adds, due to the gown’s construction. “There are no side seams; everything comes together in draping and the gathers on the front and the back,” he notes. “It makes the construction quite unique, because nothing is interrupted, and everything must be very precise. But it really showcases her gorgeous body, because there’s nothing inside that’s helping her. That’s all her.”

The look is completed with beaded shoes by Rene Caovilla and jewels by Neil Lane and Goshwara, Woolf says. “Because of the neckline, we knew early on that statement earrings and a stack of bracelets would be the way to go,” he notes.

Woolf and Dundas agree that Latto’s 2023 Grammys nomination is sure to feel like the next natural step in a high-wattage career.

“She has the potential to be a really big star, and the fashion houses are really starting to notice her,” Woolf says. “Valentino loves her, Mugler loves her, Jean Paul Gaultier loves her — and of course Peter loves her as well.”

Adds Dundas, “Latto’s really coming into her own, so drawing that parallel with someone as iconic as Marilyn felt right for right now. Nominated for best new artist is just the beginning for her, and I’m excited to be part of that journey.”