The Power Of Two Claires: Miss Claire Sullivan Talks Designing Clairo’s Grammys Look — EXCLUSIVE

In the ultimate act of Clairo shade, the Recording Academy did not award the Charm singer-songwriter with Best Alternative Music Album at the 2025 Grammy Awards. That’s OK, though: Clairo still cleaned up like a true winner. For her first time hitting the red carpet on music’s biggest night, she chose to keep her fashion within the “Claire” family and enlist one of NYLON’s favorite emerging designers, Miss Claire Sullivan, to make the ’90s draped dress of her dreams.

Sullivan is not new to dressing musicians, with memorable looks on Addison Rae and Charli XCX already firmly placing her among the go-to brands for pop’s hottest girls. Not only do Claire and Clairo share a name (Clairo’s real name is Claire Cottrill), but upon working together, they realized they had “an immediate creative synergy, an unspoken understanding of what we were about to build together,” Sullivan tells NYLON. “Beyond the references and the craftsmanship, this had to be about Claire. She has such a palpable energy, and this is a huge moment for her.”

As with everything she does, Clairo came into the preparations with a vision. Her stylist Nancy Kote started working with the singer during her Charm tour, where they honed in on her “2011 mashed up with French New Wave” look, Kote tells NYLON. “It’s playful, sexy, teasing, but so darling.” For the Grammys, Clairo knew what she wanted, Kote says: “It began with this amazing photo Clairo shared of Krysten Ritter wearing this 2005 Vivienne Westwood dress from the Dressed to Kilt show. It has this shipwrecked-doll energy that spoke to both of us.” After seeing that initial photo, Kote took to mood-boarding runway photos from brands like Westwood, Christian Dior, and Valentino to capture the mood of “billowing fabrics and mismatching textures and patterns contrasted with tailored elements,” which Kote knew Sullivan would nail.

And nail she did. When Clairo and Kote came to Sullivan in mid-December, they provided her with the “gift of time, which is the ultimate luxury. We were able to sink in and let the process unfold in such an intentional way: exploring, refining, making real choices instead of rushing through them.” The “North Star” of the look, she says, was “sexy, soft, light, and playful.” While the Grammys is an intense night, Sullivan wanted to make sure the whimsy and playfulness integral to her designs shone through, which explains the polka dots — and inspiration taken from the toile she draped with (seen above).

She took cues from the mock version of the dress to pick the buttery silk taffeta they ended up with. The first fitting was as charming as the Charm singer deserves. “I draped the bustle element of the skirt directly on Claire in real time. There’s something almost divine about shaping a garment on the person it’s meant for. I love that the people I collaborate with get to experience the process firsthand, and I know that was something Claire was grateful for.” A few more fittings, then off to the Grammys she went. Kote and Clairo decided on a teeny-tiny chainmail pochette and some gray Mary Jane heels to complement the dress, and with Clairo’s brand-new darker hair color, her fresh mauve lip made sense.

While she didn’t walk away a winner, she won our attention with her Vivienne Westwood by way of Bushwick dress (and best accessory, as seen on her Instagram), which we could tell she felt comfortable, sexy, and delightful in. It’s rare the process is as equally enchanting as the end result in what is usually a manufactured, larger-than-life event, but with two Claires at the wheel, as Sullivan says, “Every part of this piece was designed and constructed with such intention — it’s been a truly fabulous experience.”