Alyssa Milano’s Y2K Whimsy at Usher's Birthday Party • CelebMafia

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.

The year 2002 feels like a lifetime ago, a moment when the red carpet was less about grand, theatrical couture and more about a certain kind of downtown, rock-star casual. This is the era Alyssa Milano navigates with an expert hand at Usher’s “A Night of Masquerade” at The Highlands Hollywood. She unveils a look that’s a perfect snapshot of the time: a sleek black slip dress, its classic silhouette given an edge with a high-cut slit that offers a glimpse of leg. The real story, though, is the contrast—the texture, the unexpected layering.

Over the slinky dress, she wears a chunky, dark knit cardigan. It’s not just a cover-up; it’s a stylistic statement. The open-weave texture and ragged edges lend a soft, lived-in quality to the otherwise polished look, a nod to the era’s bohemian leanings. Her accessories, too, are understated yet impactful. A chunky silver bracelet and delicate, barely-there strappy heels (a favorite of the period) ground the look, while her hair, a simple ponytail with loose, face-framing pieces, completes the vibe. It’s a study in balance: the sleek against the slouchy, the formal against the carefree.

Alyssa Milano’s Y2K Whimsy at Usher’s Birthday Party

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