Anne Hathaway Elevated The Controversial Y2K Skirt-Over-Pants Style

Fashion girls often look to the past for outfit inspiration. After all, trends are cyclical, and what’s become passé can always come back more popular than ever. Armed with that knowledge, the chicest stylistas often pull from the archives, rocking decades-old pieces on red carpets, or recreating iconic looks from years prior, referencing trends of real-life celebs or paying homage to fictional characters (e.g. Carrie Bradshaw).

However, there are a handful of A-listers — nay, icons — who can reference themselves, harkening back to styles they wore way back when. One such icon is Anne Hathaway.

Anne’s Y2K-Inspired Look

On Monday, Oct. 20, the Devil Wears Prada star attended the God’s Love We Deliver 2025 Golden Heart Awards in a low-key ensemble. Matching the black carpet, she kept to a similarly inky palette. Despite the monochromatic take, she still managed to steal the show with her play on one of the noughties’ most controversial trends: the skirt over pants.

In head-to-toe Michael Kors, Hathaway wore a nondescript oversized black T-shirt with sleeves that draped past her elbows. To elevate the casual piece, she paired it with a flowy midi skirt, which she wore over her trousers.

She threw on a belt and looped it around for an effortless vibe and further accessorized with pointed-toe pumps and a massive envelope clutch. For a hint of gold, she added layers of gold bracelets and a necklace.

Her OG Dress-Over-Pants Ensemble

Way back when, during what’s now clearly the most chaotic decade in fashion history, celebrities layered their pieces with gusto because heaven forbid you only wore one tank top, a belt through actual belt loops, or one choice of bottoms. (Why choose between pants and a skirt or dress when you could rock both?) So, Hollywood’s it girls took to the layering extravaganza — Hathaway included.

In 2004, the actor attended the premiere of Ella Enchanted wearing a knee-length fuchsia pink halter dress with floral details over flared jeans. The outfit, which she completed with a floral green coat and pointed-toe pumps, landed in fashion’s hall of fame as the poster child for the dress-over-pants look.

Clearly, her love for the layered look hasn’t wavered. Now, it’s just more streamlined and grown-up.