The fashion world is witnessing an unexpected resurgence of a defining trend from the early 2000s: the art of wearing dresses or long tops over pants. Once a quirky staple of the Y2K era, this layered aesthetic, previously seen on pop culture icons like Anne Hathaway and Miley Cyrus, is now being reimagined by a new generation of red carpet stars. This revival not only brings a nostalgic touch to contemporary style but also offers a fresh, sophisticated approach to layering, proving that what was old can indeed be new again, especially when given a modern twist.
This week alone provided ample evidence of this trend's renewed popularity. Actress Ayo Edebiri, for instance, graced the Los Angeles premiere of 'Ella McCay' in a long, intricately embroidered vest from Chanel's pre-fall collection, worn elegantly over a classic white T-shirt and denim jeans. While not a dress in the traditional sense, the ensemble perfectly captured the spirit of the dress-over-pants layering, showcasing how fluid and adaptable the concept can be.
Across town, at a SAG-AFTRA event in Los Angeles, lifestyle mogul Gwyneth Paltrow offered her own polished take on the trend. She appeared in a chic Marni outfit, featuring a long, sleeveless gray polo dress layered over a pair of pleated gray dress pants. Her ensemble seamlessly blended the casualness of a polo with the formality of tailored trousers, demonstrating a sophisticated evolution of the Y2K style that aligns perfectly with today's stealth-chic sensibilities.
Beyond these recent sightings, other prominent figures have also championed the dress-over-pants look. Elle Fanning made a statement at the BFI London Film Festival, pairing a black sequined tank dress by Simone Rocha with trousers. Similarly, Michelle Williams opted for a white asymmetric Proenza Schouler dress over dress pants at the 2025 CFDAs in New York, embodying a modern elegance. Even Jennifer Lawrence has embraced a similar 'skant' style—a skirt-slash-pant hybrid—in her off-duty wardrobe, further solidifying the trend's versatile appeal.
With fashion runways hinting at a gradual reintroduction of the dress-over-pants or skirt-over-pants silhouette for several seasons, its current popularity suggests it's a trend worth adopting this winter. Beyond its aesthetic appeal, the practical benefit of additional layers for warmth during colder months is undeniable. These contemporary interpretations by style leaders prove that this Y2K-inspired combination can transcend its origins, offering a look that is both sophisticated and fashion-forward, far removed from its more casual, early-aughts predecessors.