It's Happening: People Are Wearing Dresses Over Pants Again

Ashley Tisdale is shaking.

Dress over pants pink runway look and ashley tisdale side by side

Valentino / Getty Images

If you've been on the internet any time in the past year, you may have noticed that many people have embraced the resurgence of Y2K fashion in all its glory. Hunting for vintage Juicy Couture tracksuits, low-rise jeans, and funky hair accessories is the du jour trend of the moment, but with the good also comes the bad. Now, a trend that we all tried to lock away in the darkest parts of our minds is also making a comeback. It’s the dress/skirt over pants combo. If early 2000’s Ashley Tisdale and Miley Cyrus immediately come to mind—we're right there with you. 

If you aren’t familiar with the trend, allow us to enlighten you. Here’s a quick recap: In the peak of Y2K fashion, many celebs of the time were pairing sequins fit and flare skirts over bootcut denim or long baby doll dresses over skinny jeans. This look was not for the faint of heart—and still might not be a style for everyone. But, hear us out: there is a way to go about this trend and look effortless instead of mismatched.

Miley Cyrus Wearing a dress over jeans y2k

Getty Images

This go-to Disney star pairing was first sighted in Spring ’22 collections and is now carrying into Fall/Winter ’22. So, it's safe to stay this styling choice is sticking with us through to the colder months into spring. This trend has been elevated on the runway with matching fabrications, pairing a dress or skirt back to similar bottoms, or matching colors for a sophisticated monochromatic look. Another interesting iteration is the illusion of pants under skirts and dresses. Styling wide scrunched over-the-knee boots give a pants-like appearance under long dresses and skirts.

Whether you love it or hate it (or just love to hate it), here is the proof. Behold: a round-up of a few Fall/Winter 2022 Fashion Week looks that may ease your mind as this layered trend makes a sneaky comeback.

01 of 07

Play With Texture

Chloe runway leather dress worn over gray trousers

Getty Images / Chloe

Chloe played up this trend not once but twice. We love the matching tan leather button-down and midi-length skirt layered over a softer textured trouser—offering contrast in color and texture.

02 of 07

Sarongs for Summer

Knit pink and orange set with matching sarong over pants

Getty Images / Etro

Etro’s take on the skirt over pants trend is with a knitted sarong instead of a traditional skirt, which is not as bulky over coordinating pants.

03 of 07

Go All-In on Y2K

Rave Review Y2K Cargo pants with plaid skirt

Rave Review

Rave, similar to Etro, opted for a skirt with less coverage. They paired a plaid skirt with the sides cut out over black cargos. The styling is very on beat with the Y2K trend while still looking current.

04 of 07

Try a Fitted Look

Serena Williams in sheer off white dress and matching pants

Getty Images / Off-White

The iconic Serena Wiliams is even in on the trend. Seen modeling the dress over pants combo for the Off-White show, she wore a sheer dress layered over a corseted slip with ruched fitted pants. The layering is done with pieces that tonally work with each other. The bottom layered long sleeve top matches the pants while using the dress to break it up.

05 of 07

Denim on Denim

Denim jeans with denim dress on top


A key concept in reimaging this trend is matching fabrications. Colville combined the already trendy patchworked denim with a belted denim buttondown dress over matching wide-leg bottoms, creating a sophisticated shape.

06 of 07

High Boots as Pants

Grey Skirt over matching grey boots


Another interesting take is high-leg boots that give the illusion of pants styled under longer skirts and dresses. You can see an example of this styling at Fendi’s recent show. They had coordinated over the knee boots with midi-length pencil skirts. The matching fabric for the skirt and boot helps to give the illusion of pants by not being done in a traditional boot fabrication.

07 of 07

Color Theory

Pink valentino ruffled dress with matching pink pants

Valentino / Getty Images

Valentino had hands-down our favorite take on this trend: styling a hot pink sheer floor-length buttondown over matching tailored trousers. This look makes dresses over pants feel more approachable.

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