Chappell Roan Always Serves Up Over-the-Top Looks—Onstage and On the Red Carpet

No matter the occasion, we can always count on Chappell Roan to deliver a showstopping look.

While the 28-year-old singer has become known for her soprano synth-pop, she’s cultivated a campy, drag-inspired, pop-culture-laden image to go alongside it. Chappell turned to stylist Genesis Webb to fashion her into a pop star. The two met on the set of an editorial shoot where Webb was assisting Nicola Formichetti, and the two bonded over their Midwestern roots. “The trashiness is there with us,” Webb told Vogue.

While the two have tapped brands like Thom Browne, Rodarte, and Mugler to create Chappell’s singular image, they have also shone a light on craftsmen and artisans. Leather artist Zana Bayne created her WrestleMania Lollapalooza look, VMAs armor, and SNL cowgirl getup, while designer Gunnar Deatherage was responsible for her Jazz Age SNL promo look and Swan Lake-inspired costume.

Roan went from cult favorite to overnight sensation, culminating in her 2023 debut, The Rise and Fall of a Midwest Princess, which earned her an Album of the Year nomination at the Grammys—and a win for Best New Artist. Since then, she has pushed the boundaries of her sartorial vision, best exemplified by the Mugler nipple-ring dress she wore on the 2026 Grammys red carpet—complete with prosthetics and temporary, Medieval tattoos.

Here, see some of Chappell Roan’s best looks in honor of her 28th birthday.