We're Still Not Over the Confusing '00s Dress-Over-Pants Trend — and Now It's Back

Even Lizzo is taking a tip or two from Ashley Tisdale's Disney days.

We're Still Not Over the Confusing '00s Dress-Over-Pants Trend — and Now It's Back
Photo: Getty Images/InStyle

To be honest, we thought society as a whole agreed never to bring back a handful of '00s trends. But, as we reluctantly embrace colorful leggings and popcorn shirts, another (and, possibly the most controversial) trend snuck in nearly undetected: styling dresses over pants.

For those who lived through round one of this confusing look, you might remember that nothing was off-limits when it came to how to wear it. Pairing skinny jeans with a silky fit-and-flare? Go ahead. What about layering a pleated skirt over cropped cargo pants? According to Ashley Tisdale or Miley Cyrus' old outfits, all signs pointed to yes.

Dress Over Pants
Mirek Towski/FilmMagic
Miley Cyrus
Jesse Grant/WireImage for Backstage Creations

Still, despite this trend's complicated past, we're admittedly being sucked in once again. After seeing a handful of long tunics and pants pop up in both spring and fall 2021 collections, we really began to reconsider, wondering if this was simply another creative layering technique to add to our list. And now that we've realized Lizzo's on board, layering a cute, ruffled pink dress over jeans? We're totally tempted to test out the look.

To be honest, we are a bit wiser now, and do know how to avoid super sweet and cheesy, balancing out the look with chunky boots and opting for elevated designs. With a few quick switches, it's possible to make dresses over pants look effortless, comfy, and cool, rather than chaotic.

If you're still not convinced, that's ok. We've got plenty of proof and tips for wearing this mismatched pairing. Hey, if UGGs and mid-section belts can break through the "never again" barrier, dresses-over-pants can, too.

The Dress-Over-Pants Trend Appeared in a Number of Fall 2021 Collections

Dress Over Pants
Courtesy Louis Vuitton

While sheer tunics styled over pants popped up for spring 2021, it wasn't until we spotted the trend for fall that we realized the comeback was inevitable. This layering technique graced the runway at Louis Vuitton's show, tempting us to wear our mini dresses with a pair of jeans.

Things Are Slightly Sleeker Now

Dress Over Pants
Courtesy of Rosetta Getty

The new way to wear dresses over pants is to skip some of those outrageous, playful little extras (ex: a feather boa) and don't overdo it. Keep your layers simple and structured, just like this look from Rosetta Getty's Fall 2021 collection.

Spring 2022 Offered Up Even More Outfit Ideas

Dress Over Pants
Frazer Harrison/Getty Images

Rachel Comey, for instance, embraced the trend through a matching set.

Dresses Over Pants
Victor VIRGILE/Gamma-Rapho via Getty Images

Proenza Schouler proved a pop of color was always welcome, while giving things a preppy twist with black slacks and loafers.

Dress Over Pants
Peter White/Getty Images

Louis Vuitton once again urged us to give dresses-over-pants a try, easing us into the look with a open-front layer styled over jeans.

And the inspiration doesn't just stop there. Tons of celebrities and street style stars are on board with this look these days, providing us with numerous ways to pull off this throwback outfit combo.

Style a Breezy, Printed Dress Over Jeans

Dress Over Pants
Kirstin Sinclair/Getty Images

Long, short, ruffled, knit — no matter which design you choose, the results will be fun and eye-catching.

Monochromatic Is Always Cool

Dress Over Pants
Jacopo Raule/Getty Images

As Jaime Xie shows us, a matchy-matchy pairing will come across as an intentional set, looking easy and effortless rather than over-the-top.

Test It Out With a Long Button-Down

Dress Over Pants
Neil Mockford/GC Images

Or even a long tunic. When you have the option to quickly unbutton or tuck in your top layer, the dress-over-pants look will feel like less of a commitment, and you can always switch it up if you're not feeling it later (although clearly, the trend Zendaya-approved).

It's Perfect For Unpredictable Weather

Dress Over Pants
Christian Vierig/Getty Images

Now you can wear a dress and keep your legs warm, no problem.

Think Comfy

Dress Over Pants
Christian Vierig/Getty Images

Forget the skinny jeans (for a moment) and try loose designs, like a long, breezy, caftan dress over wide-leg pants. You can also switch out your jeans for trousers or knit bottoms, allowing this outfit to become one you can wear for a variety of occasions — even just chilling at home.

Stick with Something Sheer

Celebrity Sightings In New York City - September 12, 2021

While working up to an actual everyday dress, try a sheer layer like Rita Ora. It's still the same idea, but a more subtle and less in-your-face approach.

Make the Most Out of Your Wardrobe

Dress Over Pants
Christian Vierig/Getty Images

Have a mini dress that unexpectedly shrunk and now seems a tad too short for your liking? Instead of getting rid of it, try your hand at this trendy layered look and style the piece over some pants.

Say Yes to the Side-Slit

Dress Over Pants
David M. Benett/Dave Benett/WireImage

Many celebrities who have embraced this trend — including Phoebe Dynevor — have opted for a dress with a side slit, playing around with proportions. While longer dresses-over-pants have a tendency to cut you off and make you appear shorter, seeing a little more leg has an elongating effect, solving the issue in a flash.

Take a Big Risk

Dress Over Pants
Karwai Tang/WireImage

Of course, you don't have to keep your outfit on the tame side. Celebrities like Hailee Steinfeld have gone with more voluminous and whimsical dresses, balancing out puff-sleeved designs with classic bottoms such as black pants.

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