Pleated Trousers Never Go Out of Style—These Are the Ones Worth Buying Now

Want an updated take on the classic workwear staple? Favorite Daughter gives the tried-and-true staple a sporty twist with the trim at the waistband. It’s a fun and unexpected touch for the office-adjacent garment.

Madewell is leaning into the barrel leg with its new silhouette. We love the idea of styling this with a classic tank top and a boxy blazer for a relaxed but business-ready ensemble.

This is the pair of pants that made senior fashion commerce editor Dale Arden Chong ditch her most-worn jeans for the better part of winter (and reader, she’s almost always in jeans). She claims they’re comfortable, ultra-flattering, and an easy option for when you don’t know what else to wear but still want undeniable polish.

The foolproof way to stay warm without adding too many layers is with a pair of wool-cashmere blend pants. A.L.C.’s take gives a true borrowed-from-the-boys touch with an extra-wide leg that will make any look feel effortlessly cool.

Leave it to Khaite, one of the coolest brands out there, to create a seriously good pair of trousers you’d want to wear to the office and drinks after work. The tapered leg emphasizes the volume the pleats create, and it’s also the perfect reason to show off your heels.

Money’s on the idea that these will be one of your go-to pairs. The wider leg isn’t so wide that the silhouette feels trendy, the pants are long enough to puddle perfectly, and that high-rise will truly never get old. Plus, for under $200, it has an impeccable cost-per-wear.

When associate fashion commerce editor Meg Donohue first mentioned these were from Lululemon (and that she loved them so much she wrote a story on them), we were pleasantly surprised. These are ultra-soft and so much more comfortable than they look. If you’re into stealthy comfort, these are for you.

In case you don’t already know, Gap is really good right now. I’ve been loving nearly everything they put out, and these pants are no exception—especially for that under-$90 price point.

A lot of these pants are twill and wool, but a satin pair of trousers is just as worthy of a spot in your rotation as the others—and these will feel perfect for the moments you want to be a little dressed up. Whether you wear these with a T-shirt, a sweater, a button-down, or even a sleeveless halterneck top for the sultry occasions, these will never fail you.

Yes, it’s a hefty price tag, but when you factor in The Row’s commitment to quality materials and craftsmanship, the timeless design, and this gorgeous dark chocolate hue, you’ll see just how much of an investment in your wardrobe this can be.

If you plan on keeping your pleated pants forever—and trust, they will be in style for that long—then a pair from Ralph Lauren is the way to go. These expertly crafted pants ooze sophistication, from the long inseam to the mid-rise waistband and quality fabrics. And FYI: The pleats are present on both the front and back.

Assistant accessories editor Madison Rexroat isn’t one to lean into the season. Instead, while everyone is still dressing for the colder days, she’s looking toward these 100 percent linen pants as a way to “pretend I’m on vacation when I’m really just going to the office.” As for the inevitable wrinkles that appear with this type of fabric, she says, “Embrace them—or get them in black and don’t even worry about it.”

For Chong, these pleated trousers are filed under her “essentials” list. “For something a bit more polished, you can’t go wrong with one of Tibi’s most iconic silhouettes: the Stella,” she says. “With a high waist and pleated details, these wide-leg trousers are the office essential everyone needs in their closet. Personally, I’d style them with a classic T-shirt and loafers with a half-slip layered over it, but really, these will go with just about anything,” she adds.

Model Elsa Hosk’s clothing label has rapidly grown in popularity thanks to pieces that consistently resonate with fashion lovers. Take these pleated trousers, for example—they have the perfect drape, pleats, length, and volume. Keep in mind: The 100 percent wool will require trips to the dry cleaner if you want to maintain its quality, but we believe they’ll make the perfect fall or winter pants.