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.

Alyssa Milano’s Y2K Whimsy at Usher - 1 Alyssa Milano’s Y2K Whimsy at Usher - 2 Alyssa Milano’s Y2K Whimsy at Usher - 3 Alyssa Milano’s Y2K Whimsy at Usher - 4 Alyssa Milano’s Y2K Whimsy at Usher - 5 Alyssa Milano’s Y2K Whimsy at Usher - 6

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

The red carpet at a post-Grammy party is a different beast from the main event—it’s where celebrities loosen up a bit, trading high-stakes couture for a style that’s a touch more personal. And in 2002, Alyssa Milano perfectly captured that mood. Her ivory mermaid gown is a masterclass in delicate, intricate detail. The dress, with its plunging V-neckline, features a lace overlay that creates a soft, almost ethereal texture. The silhouette is pure early 2000s, hugging her figure to the knees before flaring out into a soft, romantic ruffle at the bottom.

Alyssa Milano’s Ivory Romance at a Post-Grammy Party - 7 Alyssa Milano’s Ivory Romance at a Post-Grammy Party - 8 Alyssa Milano’s Ivory Romance at a Post-Grammy Party - 9 Alyssa Milano’s Ivory Romance at a Post-Grammy Party - 10

Milano’s accessories are minimal, yet intentional. She carries a small, sparkling gold clutch—a pop of metallic that provides a point of contrast—and wears strappy, open-toed heels, which were all the rage. Her hair, styled in a subtle updo with a single white flower tucked behind her ear, is a charmingly romantic touch. It’s a look that feels both classic and of its moment, a testament to an era when a simple, well-chosen dress could make a powerful statement.

Sol Rodriguez unveils a shocking tangerine gown at the Superman premiere—a look that proves summer’s unofficial color has finally arrived (and is staying awhile).

Some red carpets are just… red carpets. Others, like the one for the Superman premiere, become a canvas for something entirely different. Rodriguez’s vibrant dress cut through the sea of premiere-night black and navy with a kinetic energy. It’s a study in controlled chaos: a one-shoulder neckline gives way to artfully draped and pleated fabric that wraps around her body, creating a subtle cutout at the waist. The color itself is a sensory experience—a vivid, almost-neon tangerine that feels like a jolt of pure sunshine. The fabric drapes beautifully, giving the impression of liquid light as she moves.

Sol Rodriguez’s Tangerine Dream at Superman Premiere - 11 Sol Rodriguez’s Tangerine Dream at Superman Premiere - 12 Sol Rodriguez’s Tangerine Dream at Superman Premiere - 13

Her styling is a masterclass in elegant restraint. She pairs the audacious gown with simple black strappy heels and a small, chic black bag, allowing the dress to remain the undisputed star. Her hair is pulled back into a sophisticated updo, a strategic choice that highlights the unique neckline and her delicate jewelry—a pair of intricate, drop earrings that echo the fluid lines of the dress. The overall effect is both modern and timeless, a look that would feel at home on a 1990s catwalk as much as it does on today’s red carpet. It’s a dress that doesn’t just attend the premiere; it sets the tone for the entire evening.