Don't Blame Katie Holmes — the '00s Dress-Over-Pants Trend Has Been Bubbling Back Up For Years

When Katie Holmes arrived at Z100's iHeartRadio Jingle Ball wearing a mini dress over her jeans, we could almost hear the world gasp. Sure, it was fine to revive other Y2K fashion choices, like intense platform shoes, cargo pants, and ponchos, but this one? It was, perhaps, a step too far. The first time this combination hit peak popularity was confusing enough; we witnessed plenty of Disney stars rock skinny jeans with fit-and-flares and layer pleated skirts over capri pants. Why was Holmes, a known trendsetter (remember that Khaite cardigan?), trying to make us do it all over again ahead of 2023?

The truth is, she's not to blame (nor is her stylist, Brie Welch). The actress was simply following the lead of the fashion world, since the trend has been bubbling back up — albeit, slightly under the radar — for a few years now. As far back as Fall 2021, Rosetta Getty was showcasing a white shirtdress styled over black trousers. And by the time the next season rolled around, other brands were happily hopping on board, experimenting with the same whimsical styling trick.

For Spring 2022, Rachel Comey sent a matching dress-over-pants set down the runway while Louis Vuitton paired a slip dress with jeans. For Fall 2022, Chloé made a similar move with an all-beige outfit that consisted of light trousers and a leather skirt.

However, Fashion Week is far from real life, and we know a ton of unusual combinations never make it past the catwalk. But soon, celebrities and street style stars were testing out the look. By Nov. 2021, Lizzo was posting videos of herself in dresses over jeans, and around the same time, Hailee Steinfeld showed off a similar outfit on the red carpet.

Maybe Holmes — who completed her own red carpet outfit with sporty sneakers rather than heels — was offering us a more athleisure alternative when it comes to wearing this combination. After all, designers are still big fans: for Spring 2023, we spotted dresses over pants at Sacai, Proenza Schouler, Collina Strada, and Chopova Lowena (a Dua Lipa favorite), just to name a few.

There are a handful of ways to subtly rock the dress-over-pants trend if you're tempted to try it. You could go grunge with a chunky boot or opt for structured pieces, which might make the outfit feel more elevated. Instead of form-fitting bottoms, try wide-leg pants, then complete your look with a loose sweater dress or an empire-waist design.

We've welcomed back worse throwback trends (ex: popcorn shirts), so why not experiment? Check out a few of our favorite dress-over-pants outfit ideas, ahead.

Add Warmth

It's a great solution for days when tights won't cut it. Play around with knitted pieces, which will help you feel extra cozy as temperatures take a dip.

Reinvent Old Clothes

If your everyday jeans feel a bit stale or you're no longer in love with that puff-sleeved dress, breathe new life into those old pieces by styling them together. Now, you have an outfit that's fresh and unexpected.

Go Monochromatic

By going matchy-matchy, your look will seem intentional — almost like a coordinated set — giving it an easy, effortless vibe instead of over-the-top.

Try a Shirt Dress or Duster

With the option to quickly unbutton or tuck in your top layer, your dress-over-pants outfit will feel like less of a commitment. You can always switch things up if you're not feeling it later (although clearly, the trend Zendaya-approved).

Throw It Back to Y2K

Lean into the early '00s and go full Disney star by pairing your dress with cargo pants and arm warmers. Somehow, we know Gen Z will love it.

Embrace Seasonless Fashion

Once upon a time, slip dresses were solely a summer staple, but not anymore. Get more wear out of your favorite breezy styles by layeing them over leather pants and a turtleneck.

Be Bold

We're big fans of neutrals, but on days when we're craving excitement, nothing beats a colorblocked outfit. By combining two bright colors, like a yellow dress with red pants, you'll essentially be nailing multiple trends at once.

Break Out the Basics

Roomy trousers are a great alternative to jeans, especially on days when the goal is something less constricting but elevated. Pair your basic black pants with a knitted dress for a sweet winter ensemble that works for both the office and date night.

Reuse and Recycle

If you have a mini dress that sadly shrunk in the wash and is now too short for your liking, don't get rid of it. Simply add a pair of pants underneath in order to revamp this old favorite.