Alyssa Milano

Alyssa Milano attends the Los Angeles launch party for Dead to Rights in 2002, unveiling a perfect-10 look that captures the playful, low-rise aesthetic of the early aughts.

Alyssa Milano attends the Warner Music Group Post-Grammy Party, unveiling a frothy ivory gown that’s a perfect-10 encapsulation of early-aughts glamour.

Alyssa Milano attends Usher’s 2002 birthday party in an effortlessly chic ensemble, fusing a high-slit slip dress with a playfully bohemian cardigan for a dose of turn-of-the-century cool.

Alyssa Milano attends Justin Timberlake’s ‘Justified’ release party, putting a fresh, asymmetrical spin on the little black dress—a silhouette that defined the early 2000s (and feels surprisingly current).

Alyssa Milano dialed up early-aughts edge—strapless violet, belted greys, and a metallic clutch—at WB’s star-packed summer bash in Hollywood, July 2002.

Alyssa Milano leaned into bohemian ease—floral skirt, sheer stripes, and a choker with bite—at the 2002 LA premiere of Picturing A New South Africa.

Alyssa Milano’s 2003 photoshoot with Steve Shaw showcased her elegant style, blending sophistication and modernity in a stunning outdoor setting.

Alyssa Milano’s 2001 photoshoot with Tyler Demogenes captured her bold and confident style, reflecting the edgy aesthetics of the early 2000s.

Alyssa Milano, “Charmed” star, stunned in a sultry Maxim photoshoot, highlighting her breakout appeal in March 1998.