Grammys: The 40 Best Beauty Looks of All Time

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 updo. 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. Over the past decade, Rihanna and Lady Gaga have whipped through a lineup of unforgettable beauty moments, and Beyoncé has continued to serve up a variety of show-stopping looks, from a glossy wet-look bob and stamp of deep crimson lipsticks to a gilded crown worn with flaxen curls that fell down to her baby bump to Botticelli Birth of Venus effect. In the years to come, we will surely see more from newcomers like Billie Eilish, who made her Grammys debut with neon green roots and a Gucci logo manicure to match, and Rosalía, who sported monochrome rose makeup punctuated by cat eyes with bejeweled nail art.

From Madonna s geometric black bob to Beyoncé’s golden headpiece, these 26 memorable moments demonstrate the undeniable power of live-for-the-moment beauty.