Whoever was in charge of the wardrobe department at Disney and Nickelodeon in the early 2000s deserves some sort of medal. They really did a fantastic job, to the point that I still find myself looking back at photos from Hannah Montana as outfit references every so often. (It’s okay, though. Miley Cyrus does the same.)

I know I’m not the only whose childhood style was strongly informed by the concept of wearing a dress over pants. In the early aughts, all the fashionistas were in on it. Think Mischa Barton, Garcelle Beauvais, Anne Hathaway. If there’s someone that was cool between 2002 to 2007 (ish), I bet I can find you a picture of them pairing jeans with a babydoll. There was a brief renaissance around 2018, but then the combo went mostly quiet. Until now.

Here’s the (bootcut) kicker: The look is back, and not just in our That’s So Sweet Life of Hannah Montana-based fever dreams. It’s everywhere. Ahead, discover everything there is to know about the dress-over-pants trend’s grand return, including how to make it your own.

The Dress-Over-Pants Trend

We’ve seen dresses over pants literally everywhere this winter. Cool girls like Stephanie Suganami, Gwyneth Paltrow, Elle Fanning, and Jourdan Dunn have all given the look a go. Keke Palmer did it at the Met Gala last year, as did Michelle Williams at a CFDA event and Kendall Jenner at Vogue World. And of course, Margot Robbie wore a vintage John Galliano take on the trend for her Wuthering Heights press tour.

We’ve seen dresses covering up belt loops on the runway, too. Louis Vuitton’s Spring/Summer 2026 collection was styled as such, as was Balenciaga’s. and more. And before super recent times, hints that they were returning were everywhere.

Remember the little slips that we started layering under shirts in the last few years? That was an indicator. The lace tunic/matching pant set from BAOBAB that I’m constantly getting ads for (because I’m engaging, I want it) is, too. They’re calling them tops nowbut these long shirts could absolutely be dresses if you’re brave enough. The language will change soon.

How to Make It Work

The most important thing to take into consideration here is the length of the dress and the shape of the pants. A mini or midi-length is always going to work best on top—maxi can distract from what you’re trying to go for.

Meanwhile, the pants should have a bit of flow to them. Or, if you go cropped, you want them to have enough structure that it doesn’t look like you’re just wearing leggings. (That’s a little too Disney Channel, I fear.) A sheer, floaty fabric is always fun for the skirt, too. That way your pants can peek through.

Specific style-wise, there are so many ways to go. Just pick your favorite! I’m sure there’s a dress in your closet that you’ve been missing since last summer. That’s the one to try here.

Shop the Look

If you’d like to ease in, you can also go for a matching set (the one I was talking about earlier also comes in polka dots). Keep scrolling for some dresses and pants to add to your closet, should you be missing one or the other—as well as a few options that are already paired for easy outfitting.