Crisp fall temperatures invite endless opportunities to layer autumn staples like sturdy barn jackets, sumptuous sweaters, and tailored trench coats. And while I’m looking forward to doing just that, I’m even more intrigued by a layering trend that feels a little less expected. Enter the Y2K-era dress-over-pants look—already sweeping through fashion’s inner circle this season, led by none other than one of the industry’s ultimate tastemakers: The Row.
Meanwhile, Marie Claire’s senior news editor, Halie LeSavage, has noticed the controversial trend during her recent visits to Copenhagen Fashion Week. “Every time I touch down in Copenhagen, I see stylish women layering dresses over loose trousers or wide-leg jeans,” she says. “Sometimes they contrast ripped-up denim with a flouncy Cecilie Bahnsen dress, and other times they double-up on Scandi minimalism with a neutral T-shirt smock and coordinating pants.”
LeSavage tells me that she’s tempted to try the retro look for herself, and honestly, I’m right there with her. I'm also drawing inspiration from Ganni’s Fall 2025 runway show, which featured a floral knit dress paired with billowing jeans, and taking notes from street style, where savvy city residents have mastered the art of pairing frilly lace frocks with streamlined slacks.
If you’re intrigued by the idea of wearing dresses over pants, scroll on. Ahead, you’ll discover an edit of 10 outfit formulas that feel more timeless than trendy. Not to mention, they’re surprisingly easy to assemble.
Autumn Hues
This easygoing look will turn you into an outfit repeater.
Now is the ideal time to try out fall’s brown and denim color combo. Think about a tiered mini dress in a deep mocha mousse shade, and complete your look with a matching jacket, cuffed jeans, a white T-shirt, and shiny ankle boots.
Double Denim
Canadian tuxedos are so back.
Add a soft touch to your jean-on-jean look with a lace-trimmed dress, a satin scarf, and a delicate handbag. If it’s too cold for sandals, replace your open-toe shoes with boots.
Diaphanous Dressing
Here’s how to embrace the naked dress trend in a way that provides more coverage.
If you don’t want to go totally sheer, layer a lingerie-inspired dress over tailored trousers and a plain top. It’s an outfit that feels sultry yet sophisticated.
Sweater Weather
It’s officially time to bundle up.
For fall days that feel more like winter, opt for a cozy sweater dress and long bottoms to keep you warm. Paired with cushioned ballet flats and a functional tote, this casual look is ideal for on-the-go moments.
Seeing Green
Who says you can’t wear saturated shades for autumn?
According to fashion stylist Sophie Lopez, no fall wardrobe is complete without a touch of brown and green. For styling the popular color combo, take cues from the showgoer in the picture above and add some white pants into the look.
Go Monochrome
Keep it simple by choosing one color to wear from head to toe.
You can never go wrong with a monochromatic outfit. This sophisticated look makes autumn's chocolate brown color trend look undeniably chic.
Party Attire
Save this look for your next night on the town.
Dance the night away in this vibrant going-out outfit. Embellished with a sleek leather jacket, it’s the perfect mix of style and drama.
Oh-So Bohemian
Give the dress-over-pants trend a free-spirited treatment.
Embrace a boho-chic look with this ‘70s-inspired outfit. All you need is a ruffled lace maxi dress, a pair of roomy jeans, and a velvety suede bag.
Peekaboo
This sheer outfit is guaranteed to earn you endless compliments.
If you’re feeling bold, follow this street style icon's example. Just pair a sheer dress with a chunky fur coat and long, floor-length pants.
Corporate-Friendly
Workwear doesn’t have to be boring.
On office days, wear a satin dress or simple slacks. Paired with a blazer and a laptop bag, this stylish outfit can easily go from a serious meeting to a casual happy hour.
