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

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

RELATED: 12 Questionable Trends From 2011 That Are, Unfortunately, Back

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 layeingr a pleated skirt over cropped cargo pants? According to Ashley Tisdale or Miley Cyrus' old outfits, all signs pointed to yes.

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 Spring 2021 collections, we began to reconsider, wondering if it was simply a creative layering technique. And, by the time Fall 2021's virtual fashion week rolled around, and dress-over-pants pairing were aplenty? We were convinced it needed another chance. After all, we're wiser now, and know to avoid super sweet and cheesy. With a few quick switches, this trend can look effortless, comfy, and cool — aka the vibe we're going for at the moment.

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.

Once we saw this sheer tunic over loose trousers at Fendi, we had a feeling the comeback was on its way.

It repeatedly turned up in Fall 2021 collections, including Louis Vuitton, where there were a handful of long tunic, dress-like layers were styled over pants.

The trick for pulling it off the 2021 way is to skip all the playful accessories and don't overdo it. Keep the pieces simple and structured, like this look from Rosetta Getty's Fall 2021 collection.

Here are some more ideas for how to wear dresses over pants.

Yes, you can try this trick with jeans, too, not just work pants. Find a short, possibly ruffled dress and style it with flairs for a fun, unexpected combination.

It will come across as an intentional set, and looks easy and effortless, rather than over-the-top.

You don't have to go for a full dress. Try a longer-than-average shirt instead, and wear it with simple, solid pants for a commitment-free take.

Spring weather can be unpredictable, and summer nights are often chilly, too. This layering move is the perfect way to wear all those sundresses while still keeping your legs warm.

Forget the skinny jeans (for a moment) and try loose designs, like a long, breezy, caftan-like dress over wide-leg pants. This is an outfit you can wear for a variety of occasions, but also chill in when you're at home.

If you own a long shirt dress, don't button it up all the way. Keep the bottom half open so that your legs are visible, creating an eye-catching yet casual ensemble.

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.

You can create a similar vibe by layering a long shaket over some jeans. Considering this top is so versatile and easily adjustable, it's a good one for putting the trend to the test. Should you change your mind, just unbutton!

Of course, you don't have to keep your outfit on the tame side. People are already gravitating toward more voluminous and whimsical dresses, balancing out puff-sleeved designs with classic bottoms such as jeans and black pants.