I am a dress girl through and through and a bit of a pants hater. I don't find myself gravitating toward jeans or trousers, even though I want to give them a chance. It's why I haven't been able to stop layering my dresses over my pants recently. The controversial styling has been like my gateway into covering my legs.
There's something about pants that feels uncomplicated for me, and I just prefer outfits that make me scratch my head a bit. Dresses over pants offer that kind of skepticism. And like the very best styling in fashion, it's not something everyone will like. But when some people hate your look and other people love it, that's when you know you're doing something right.
Wearing a dress over pants was extremely popular in the early 2000s. And do I necessarily think that every early aughts Disney star who wore it on the red carpet did it right? No! But I do think the way it's coming back in 2025 feels entirely different.
It's not about throwing a dress over a pair of pants because it feels edgy and calling it a day. It's about playing with silhouettes and creating interesting shapes with slip dresses in funky textures and varying degrees of translucence.
That said, I understand why the look is intimidating. It's not natural to wear two things at once when you would normally just wear one. So I looked at some of my favorite street style images below to illustrate exactly how to best pull off the look this summer.
Add a tube top over a lace dress and jeans to create more shape:
Or wear a tank top over a simple dress with trousers for a looser silhouette:
Layer a sheer floral dress over baggy jeans and kitty heels for a cutesy look that still feels casual:
Go monotone with a longer dress and pants that only peek out, if you want to be subtler:
Or go all out with an embellished slip, wide-leg jeans and a statement hat:
