Best Dressed Entertainer of 2025 – Chappell Roan

From archival Jean Paul Gaultier Haute Couture at the Grammys to a rare romantic moment presented entirely on her own terms at Valentino, Chappell Roan showcased a thrilling breadth of style this year.

Even softness arrived filtered through exaggeration, theatricality, and a carefully constructed persona.

That sense of range extended to the Met Gala, where a Paul Tazewell design interpreted the night’s dandyism theme through ornamentation, and a heightened sense of character.

The year closed with Efrain Nava & Manny Robertson at the Rock & Roll Hall of Fame, delivering a striking visual ode to Cyndi Lauper. Across glamour, romance, and full-blown fantasy, Chappell proved versatility doesn’t dilute identity.

Second place: Doechii. Third: Sombr. Fourth: Lisa. Fifth: Raye.

Stylist: Genesis Webb.

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