24 Years Ago, Britney Spears Wore Her Most Underrated Look

In the early aughts, Britney Spears attended her fair share of awards shows where she made indelible sartorial marks. Her early MTV Video Music Awards appearances, for example, led to some of her most memorable outfits. There was one awards show look, however, that flew under the radar.

On Feb. 23, 2000, Spears attended the Grammys in an all-white ensemble unlike anything she’s ever worn. In contrast with her more risqué outings, Spears’ red carpet gown was an elegant page out Old Hollywood’s fashion playbook. In my humble fashion girl opinion, it was the most underrated look of her entire career.

Britney’s High-Glamour ’Fit

At the 42nd Annual Grammy Awards, Spears was nominated for Best Female Pop Vocal Performance for “...Baby One More Time” and the prestigious Best New Artist award. Channeling Old Hollywood sophistication, she wore a simple halter gown by Randolph Duke.

A dash of interest came from the item’s V neckline and cut-out strap details. The floor-length white number popped effortlessly against the deep red carpet.

Her Elegant Accessories

Her choice of accessories is what ultimately sent the look into high-glam territory. The ultimate symbol of opulence, Spears wrapped a fur stole around her arms — a luxe design from Oscar de la Renta.

While she kept her accessories mostly minimal, she did accent her look with a diamond necklace — another refined choice. The shimmery gems were perfectly framed by her sleek, straight ’do and fresh-faced makeup.

Her Other Grammys Look

Just a day prior, at a pre-Grammy party, Spears rocked a completely different vibe, which skewed closer to her naughties pop star persona. She wore a silver crop top that sparkled with bejeweled details.

Playing on textures, she paired the top with pink pants, complete with all-over sequins, a rhinestone-encrusted waistband, and a feathered hem. She also added a sheer organza shawl.

She may not have won the Grammy, but she was definitely best-dressed.