Anne Hathaway unveils a cool, confident look on the set of The Devil Wears Prada 2, channeling off-duty editor-in-chief vibes—a sharp, almost-too-perfect-for-life dose of New York street style.
The streets of New York City are the ultimate runway, and on a breezy day in August 2025, Anne Hathaway was caught in her element. Her look is a playful wink to her past as Andrea Sachs, but with the high-fashion edge of someone who’s made it. She wears a crisp, oversized white shirt left untucked over a simple white skirt. It’s a silhouette that feels both relaxed and intentional, a quintessential summer uniform for a woman on the move. But the accessories tell the real story.
Hathaway pairs the white ensemble with a black Favorite Daughter the Jordan Belt , a bold line that breaks up the monochromatic palette and gives the outfit structure. Her choice of footwear—chunky black sandals—is a practical and stylish departure from the stiletto-wearing days of her character’s past. She carries a chic, black-and-white checkered tote, and her face is framed by a pair of sleek black Otra Hazel Sunglasses . The whole look is a testament to the power of thoughtful styling. The vibe is a little bit casual, a little bit high-fashion, and all-around perfect.
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.
There’s a certain nostalgia that hits when you look back at Y2K fashion, a moment when style was less about perfection and more about personal expression. At the Dead to Rights video game launch party in Los Angeles in August 2002, Alyssa Milano perfectly embodies this vibe. She wears a simple white tank top paired with low-rise, flare-leg jeans—a silhouette that defined the era. The real showstopper, however, is the oversized, white crocheted shrug draped over her shoulders. It adds a bohemian, carefree layer that contrasts with the clean lines of her top.
Her hair is styled in a choppy, textured bob with swept bangs, a signature look of the period. A small, blue hobo bag adds a pop of subtle color and continues the relaxed, effortless theme. Milano’s look is a testament to the power of mixing textures and silhouettes to create a look that is both stylish and lived-in.
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.
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.
