The Grammy Awards love Chappell Roan. And considering the eight-time nominee and one-time winner hit the 2026 Grammy Awards red carpet in a totally sheer custom Mugler dress with built-in nipple rings—easily the biggest statement of the night—the feeling is clearly mutual.
Up for Record of the Year and Best Pop Solo Performance for “The Subway”, the pop maverick and her long-time stylist Genesis Webb knew tonight warranted a head-turner. So, for her red carpet look at the 2026 Grammy, they went for what fashion staff writer Meguire Hennes described in our editors’ group chat as “the nakedest naked dress I’ve ever seen.” Her burgundy red sheer Mugler dress was clipped and delicately hung from, well, her nipples and cascaded down onto the floor.
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The custom Mugler creation is similar to the see-through, nipple-accessorized gowns that walked in the brand’s Spring 2026 runway. But of course, Chappell put her distinct Midwest Princess twist on things; initially, Roan arrived wearing a matching red sheer sheath, which she theatrically removed for the full reveal.
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Speaking of reveals: When Roan turned around, she gave the cameras a peek at a massive, medieval-inspired back tattoo, plus a princess tattoo placed in the iconic “tramp stamp” location.
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Roan worked with her go-to makeup artist, Andrew Dahling, in partnership with MAC, for her glam, consisting of a light smokey eye, peachy blush, and nude glossy lip.
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Roan’s look for the 68th Annual Grammy Awards joins her already well-established archive of phenomenal red carpet looks. Last year’s ceremony alone—her first ever—was a testament to her and Webb’s wizardry as a style duo: Roan arrived at the 2025 Grammy Awards in a ball gown from Jean Paul Gaultier’s Spring 2003 couture collection, constructed of cool blue and canary yellow tulle featuring an illustration of the late master painter Edgar Degas’s “Dancer With a Bouquet.” It was accented with nests of sticks, blue flowers, and fruit ornaments along the neckline, waist, and bust. Lastly, the “The Giver” singer chose a matching feathered headdress—the authentic piece from the original collection—custom John Fluevog tall buckle boots, and sheer opera gloves to polish off her look.
On the live red carpet pre-show, E!’s fashion correspondent Zanna Roberts Rassi said that Webb had the JPG look on her vision board for 10 years, and once she procured it for Roan, she “slept with it in her room because it’s that precious.”
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Once inside, Roan changed into her second look of the evening: a custom Thom Browne ensemble comprising a denim-blue wool-and-silk cropped jacket with exposed shoulder pads, a blue corded lace corset, and a hand-pleated asymmetrical petticoat. It was theatrical, exquisite quality, and carried a strong sense of camp—all attributes that work to describe the one-of-one pop star, too.
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But the fashion fun didn’t stop there. The Midwest Princess later performed “Pink Pony Club” on the Grammy’s stage in a rodeo clown-inspired look. The custom bronze Zana Bayne bodysuit and gloves boasted Western-inspired silver studs and buckles, which went nicely with the brown and metallic Steve Madden cowboy boots.
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Annnnnd we’re not done. Cut to a handful of minutes later, and there Roan was, accepting the Grammy for Best New Artist in a pale pistachio, bow-adorned Acne Studios dress from the brand’s Spring 2025 collection. Lest we forget her topper: a yellow Piers Atkinson hennin, a fancy word for the cone-shaped headwear worn by European noblewomen during the 15th century.
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Some would say Roan is still an industry newbie. Those who’ve been following her since her YouTube days—when she was posting using her given name, Kayleigh Rose—would say her fame is a long-time coming. On the fashion front, however, it’s indisputable: Miss “H-O-T-T-O-G-O” is a certified red carpet legend, up there with the greats.
