As far as red carpet looks go, the Grammys are easily the most entertaining, especially compared with the aesthetics of the more restrained — albeit inarguably beautiful — Oscars. Since its inception in 1959, the Grammys have emboldened musicians to experiment and make statements, resulting in a catalog of unique looks representative of both era and genre. It’s the night every year we see celebrities unabashedly lean into trends: Timeless and classic this is not. Instead, it’s often a welcome breath of fun-and-risky fresh air.
Aretha Franklin embodied the ’70s glamorous bohemian aesthetic when she accepted a gilded gramophone with lids dusted in hazy silver — her dense, close-cropped Afro wrapped in a scarf. Skip ahead a decade and Joan Jett’s trademark raven shag paired with graphic pink blush and eyes rimmed in smudged onyx served as a visual portal to the ’80s. Alanis Morissette and Fiona Apple rounded out the ’90s I-don’t-care-if-you-like-it songwriter vibe with tangled and messy hair — and Britney Spears and Jennifer Lopez showed us the exact opposite in the early aughts pop-era, marked by highlighted, ironed styles, sweet smiles, and plunging necklines.
In the early aughts, Shakira shimmied onto the scene with a flushed glow and cascade of waist-skimming golden platinum spirals, as did Alicia Keys with a twinkling crystal eye statement and stunning side-slung cornrow up-do. In 2007, Beyoncé paid tribute to Billie Holiday and the jazz singer’s pièce de résistance gardenia-adored hair by wearing a fresh bloom in her hair during a performance of “Listen,” and the following year saw Amy Winehouse winning big and cemented her beauty icon status with her signature thick black flicks of eyeliner and a half-up, half-down beehive.