Alyssa Milano

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.

Alyssa Milano, beloved “Charmed” actress, captivated in a bold Ocean Drive photoshoot, showcasing her rising star power in November 1999.

Alyssa Milano, Charmed actress, sizzles in a 2002 FHM shoot, showcasing her bold allure at the height of her fame.

Alyssa Milano, Charmed star, radiates charm in a 2000 TV Guide photoshoot, highlighting her rising fame at the peak of the show’s magic.