We’ve reached the Y2K final boss: The dress-over-pants trend is bubbling under the surface with all the zest of an early 2000s Disney star.
The throwback trend — once a red carpet staple among young Hollywood — is getting a minimalist remix from brands like The Row, Hermès, and Boss, proving that the once-dated styling trick can be modern, chic, and grown-up. Now, it’s less about flouncy dresses over bootcut jeans (though, the Olsen twins did make a case for that), and more about longer hemlines and matching layers that fit into the current timeless-over-everything attitude in fashion.
While the look may be synonymous with the Kids Choice Awards, it dates back to the mid-19th century, when Amelia Jenks Bloomer and Elizabeth Cady Stanton would wear bloomer pants underneath calf-length dresses during the early Suffrage Movement, as an act of defiance against societal norms. It would eventually be embraced by the masses as a trend, arguably reaching its peak in the early 21st century.
It went away for a few decades, but Katie Holmes bravely dipped her toe into reviving dresses-over-pants at the 2022 iHeartRadio Jingle Ball Awards, donning a strapless blue dress from Tove over raw-hemmed blue jeans and a pair of New Balance sneakers. The look was met with backlash from the fashion set, but Holmes still stands by the style today, telling Drew Barrymore on her talk show that she “felt cool.”
Turns out, she was onto something: Not long after, it began appearing on the runway, and celebrities like Kendall Jenner started wearing dresses over pants more frequently.
The dresses-over-pants of 2024 put a greater emphasis on wearability and a streamlined look, giving it a more refined feel, especially for the cooler months. The Row’s pre-spring 2025 collection makes a case for slouchy pants with lacy dresses, even styled underneath sweaters — paired with flip flops, no less. The spring/summer 2025 collections are similarly infused with this intuitive layering and quirky girl-on-the-go aesthetic, seen at Rokh and Hermès in Paris: Long, tailored tops that emulate dresses with flared or tailored pants tastefully update the mismatched feel of the early 2000s outfit combination.
At Boss’s spring/summer 2025 show, models donned draped gowns over slacks and sprinkled the layering trick into office wear with mini-skirts worn over trousers. At the Garment, during Copenhagen Fashion Week, airy tailored slacks and sheer styles link up in a summer-y Scandi take on the once-kitschy trend.
“I think it adds a unique and interesting proportion to your outfit while still creating an elegance to your look,” says Kenzie Welch, a personal stylist and wardrobe consultant. However, she “can see how some may find it intimidating.” For those who aren’t sure where to start, she recommends opting for a tunic top: “It’s not too long, but still gives you the look. I also love the idea of shirt dresses or even using skirts — like a pleated option — to pair with trousers.”
To avoid the casualness of the 2000s, stylist Coco Schiffer suggests dressing it up as much as possible, with matching options from brands like St. Agni. The long strapless wool tunic paired with the gray matching pants feels like the 2024 version of wearing a blazer and mini skirt out to the club.
“The more everyday wear can get sloppy or a bit too conservative quickly, so I’d try mixing monochrome color palettes with skin showing either around collar bones with an off-shoulder neckline or ankles with a pump,” she says.
Like what you see? How about some more R29 goodness, right here?
A Brief History Of The Barn Jacket Trend
