Fashion Clothing 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. By Samantha Sutton Samantha Sutton Instagram Samantha has been working in media for over a decade and joined InStyle's team as the Senior Fashion Editor in 2019. She previously held roles at Coveteur, POPSUGAR, Refinery29, and Men's Fitness, covering both fashion and celebrity/entertainment. In her spare time, she enjoys performing sketch comedy with her friends, watching Love Island, and endlessly scrolling through social media. She is originally from Staten Island, but currently resides in Brooklyn (and sometimes, Schenectady!) with her fiancé J.T., their dog Poppy, and way too many clothes. Samantha graduated with a B.A. in journalism from Rider University. InStyle's editorial guidelines Updated on November 22, 2021 Pin Share Tweet Email 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. 8 Fall Trends You Already Have in Your Closet, and How to Wear Them Right Now 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. Mirek Towski/FilmMagic 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 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 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 Frazer Harrison/Getty Images Rachel Comey, for instance, embraced the trend through a matching set. 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. 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. 14 Sweater Dress Outfits That Aren't as Basic as They Sound 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 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 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 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 Christian Vierig/Getty Images Now you can wear a dress and keep your legs warm, no problem. Dig Those Fishnets Out of Your Sock Drawer Because They're 100% Back Think Comfy 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 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 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 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 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. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit