When the Row came out with its early Spring 2025 collection, everyone in the Bazaar office was talking about one look in particular: a dress over pants. Although it may not have been on our 2024 bingo card, it was clear the controversial styling trick was back. Maybe we were a bit triggered by flashbacks to the early Y2K era (when everyone from Lindsay Lohan to Mary-Kate Olsen herself wore dresses over pants to various red carpets)—but we were also intrigued by the possibilities.
Other designers over the years have taken a stab at this very specific styling point; Phoebe Philo at Celine in 2016 was a big one. More recently, this style was a top trend of the Resort 2025 collections (something to look forward to!). There’s something about the unapologetic, so-wrong-that-it’s-right aesthetic that strikes me as very cool, so I wanted to try it out for myself. “I’ve done it before,” I thought. “How bad could it be?” And since I’m a tall girl, some of my minidresses work best as a long tunic or top anyway.
What I found is that when it comes to dresses over pants, the options are truly endless. Whether you go more monochromatic with tonal colors or make a big statement with mix-and-match floral prints, there is something for everyone. Below, I break down seven ways to try out the style.
The Casual Look
Take your favorite silky minidress or floral babydoll and mix it with your best straight-leg classic jeans. If the print feels too precious, balance it with a bold pop-of-red sweater or utility-oriented barn jacket, two of the biggest fall 2024 trends. To finish the statement, go with an adorned sandal or Mary Jane flat.
Khaite Margot Minidress
Tory Burch Patos Slingback
The Evening Approach
Add a cool twist to your party attire by pairing a sleeveless bodycon dress with flared, fitted, legginglike trousers. For a bolder approach, go with matching silky separates to make a set that looks effortlessly chic but feels as if you’re wearing pajamas.
One way to make this look work: Be transparent—literally. For the look on the left, I threw on this amazing Maria McManus stretchy pencil skirt with a sheer panel over pants, then added my leather blazer from the Row. On the right, I’m carrying a mesh bag from Tory Burch. Either way, it helps to tap into the sheer trend to make sure your layers aren’t overpowering.
Marina Moscone Drawstring Scribble Pants
Leset Rio Bandeau Dress
Adam Lippes Eva Bonded Neoprene Flares
Tory Burch Mesh Tote
For the Office
Wearing a dress over pants to the office is all about balancing a party on top and business on the bottom—truly the best of both worlds. Going monochromatic is always a good idea, especially when styling pieces that have layers and volume. I took the gray midi skirt of my dreams and added a tonal pair of trousers and a cashmere top for a look that feels both professional and unexpected.
You can also add some interest to a shirtdress by using it as a layering piece over white jeans. Just add your favorite ballet flat and you’re ready to go.
Toteme Straight-Collar Cashmere Shirt
Maria McManus Pleat-Front Full Skirt
COS Wide-Leg Trousers
Hermès Taurillon Clemence Picotin 18
Barbour Allerston Waxed Jacket
The Row Izumi Shirtdress
Toteme White Straight-Leg Jeans
J.Crew Zoe Ballet Flats in Leather
Chanel White and Black Sequin Logo Mini Rectangular Flap Bag With Gold Hardware, 2022
Pared-Back Chic
For a more subtle approach, try playing with proportions. Take a swingy navy or black minidress and add a cream wide-leg trouser and extra-large bucket bag for an all-around oversize look. Or go monochrome by pairing a fitted cream dress with flowy cream trousers and a sporty parka; the different shapes will add dimension to an otherwise one-note look.
I also loved wearing this long-sleeved black-and-white dress with cropped trousers. The zebra stripes add a bit of fun—after all, animal print seems to be the new neutral of the season.
Arch4 Viola Ribbed Maxi Dress
TWP New Didi Pants
Rotate Zebra-Print Midi Dress
Frame Le Crop Mini Boot Trouser
The Sporty Version
High Sport’s Kick pants have a cult following. The cropped kick-flare shape offers so much versatility: You can dress them down or up, and what better way to do so than with actual dresses? I tried mine with a girly shift dress and a cool T-shirt apron dress and found that both pieces just felt right. Finish the look with an oversize bomber jacket to lean into the athletic feel of the pants, and bring in a classic element with ballet flats. (Ballet is a sport, isn’t it?)
High Sport Kick Cropped Flared Pants
TNA Brea Bomber
Rosetta Getty Apron Cutout T-Shirt Dress
High Sport Kick Pants
If You Love a Tunic
Personally, I’m sold on tunics as the new top of the season. They’re just chic. Some can serve as a minidress, but they look coolest with a pair of white jeans or raw denim. I love the idea of mixing in sculptural accessories to make a statement, so I paired mine with the Savette Pochette bag, an Aspinal of London mini woven tote (to add some texture), and my favorite Tory Burch pierced mules (which just came back in stock!).
A.P.C. Standard Jeans
Toteme Off-Shoulder Tunic
Savette Symmetry Pochette
Skirts Over Pants
Using a skirt as a layering piece feels so fun and reminds me of the way Alaïa uses flared belts to break up dresses and pants. Bubble-hem skirts are having a moment, and I love the idea of wearing one over jeans as a peplum, like an extension of the top.
I’m also into mixing florals, especially in this context. The combination of the satin pencil skirt and printed pants breathes a coolness into the otherwise precious patterns. Leaning into the garden party and/or western vibes of it all, what better way to finish the look than with a barn jacket?
Marge Sherwood Balloon Skirt (Brown Check)
Khaite Abigail Jeans
Marge Sherwood Vintage Washed Work Jacket
Prada Printed Nylonette Midi Skirt
