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Home / Celebrity Photos / Alyssa Milano’s Daring Twist on the LBD

Alyssa Milano’s Daring Twist on the LBD

Updated August 10, 2025 by Lara Parker ★Add CelebMafia on Google

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, a fixture of the late ’90s and early ’00s, had a knack for showing up and showing out on the red carpet. At the Justin Timberlake ‘Justified’ release party in November 2002 at Smashbox Studios in Culver City, she unveiled a look that was classic yet entirely of its moment. Instead of a simple slip, Milano debuted a black gown with a striking, architectural bodice. One strap wraps around her shoulder with a delicate, lacy detail, while the other—a bold, angular cut—slashes across her decolletage, creating a fascinating asymmetry. Is it a dress? Is it a statement? Yes, to both.


Alyssa Milano
Alyssa Milano
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Alyssa Milano
Alyssa Milano
Alyssa Milano

The dress itself flows in a column, the fabric clinging just enough to hint at her form without revealing too much. The texture seems to be a light jersey or a similar clingy knit, giving it a casual-cool sensibility that’s perfect for a party, not a formal ball. This wasn’t about high-drama couture; it was about modern, effortless chic. She accessorized minimally with a sleek watch on her left wrist and a pair of open-toed heels that were, perhaps, a slightly forgotten element but still played their part.

The Smashbox Studios setting itself, a hub for fashion and photography, lent an industrial, edgy vibe that her outfit perfectly complemented. Her hair, styled in soft waves with a side part, framed her face beautifully, and her deep red lip was the only splash of color needed to complete the look. This ensemble wasn’t just clothing; it was a cohesive narrative of confident, understated glamour that still holds up. It was a testament to how the smallest details—that single lacy strap, the bold slash—can elevate a look from simple to unforgettable.

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Filed Under: Celebrity Photos Tagged With: Alyssa Milano

Previous LookAlexandra Daddario’s Garden Party Chic, Bridgehampton Gala
Next Look Tricia Helfer’s Parisian Whimsy for Eclair Magazine

More Alyssa Milano Looks

Alyssa Milano posing in black blazer and sheer skirt at Bridge to Justice Gala Los Angeles May 2026Alyssa Milano at Bridge to Justice Gala LA May 2026
Alyssa Milano at Balance Premiere in West Hollywood 2026Alyssa Milano at Balance Premiere in West Hollywood 2026
Alyssa Milano’s Y2K Rebel at ‘Dead to Rights’ LaunchAlyssa Milano’s Y2K Rebel at ‘Dead to Rights’ Launch
Alyssa Milano’s Ivory Romance at a Post-Grammy PartyAlyssa Milano’s Ivory Romance at a Post-Grammy Party
Alyssa Milano’s Y2K Whimsy at Usher's Birthday PartyAlyssa Milano’s Y2K Whimsy at Usher’s Birthday Party
Alyssa Milano Debuts Whiplash Chic at WB’s 2002 Summer Party in LAAlyssa Milano Debuts Whiplash Chic at WB’s 2002 Summer Party in LA

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