I'm Running It Back to the '00s and Layering Dresses Over Pants—Here's How

In an attempt to diversify my winter layering even more as the intensity of the season trudged on, I looked to an old reliable styling hack and standard of 2000s dressing: dresses over pants.

An extra intentional layer is key in building warmth on the coldest of days. But layering pants under a dress—or something longer than a shirt or sweater—pushes the boundaries of what otherwise could be a more simple outfit. I think this can also work really well as a transitional approach from spring to summer, so these ‘fits aren't limited to just tundra conditions. It’s a weird enough combination to command the impression of having style, but it goes hand in hand with having the confidence to not let the heaviness of the layers wear you instead.

You really have to be prepared to bring a little drama. I tried three different types of pants as my base: baggy jeans, sturdy leggings, and a tapered trouser. My three dresses had to provide as much variety of texture in fabric, weight, and shape—and I actually loved all of the combos I threw together. I think they could all be interchangeable to a certain degree, so I look forward to trying out more riffs on this formula between now and summer, when my legs can finally be free.

A Sweater Dress Over Baggy Jeans

I was in New York for a quick overnight trip to style a shoot, and had intended to wear a cold weather go-to of mine: a Sacai sweater/shirtdress hybrid with wooly argyle tights and my Sacai x Ugg loafers. About 10 minutes before getting out the door on that brisk 15-degree morning, something about the flounciness of the dress with the tights seemed a little too “sweet” for the occasion. I panic-pinged Hanna, who was assisting me that day (and already on her way) to see if I should do the dress over the baggy jeans I wore on my train commute into the city instead. She has excellent personal style, so, naturally, she voted for the denim, which made the look about 10x cooler than I had planned. She was correct! The flounciness of the dress felt more like a peplum over the jeans, and the bigger silhouette brought more drama. I was super warm, and everyone on set had something nice to say about my outfit—a total win.

A Dress Over Leggings

I’ve been doing a ton of colorblocking in my winter layers (as inspired by the Prada Spring 2026 runway), and noticed this secondhand Prada T-shirt dress didn’t get nearly enough love this fall. I was trying to bring her into the fold this winter with some creative styling, because, in cotton and silk, she's rather flimsy. I layered it with a pop of red turtleneck and navy velour Alaïa leggings (an epic sample sale find) to peek out from the side slits, and topped it off with the wintry warmth of a cashmere cardi and Uggs.

I felt a little art teacher-y in this one, but I didn’t mind. It felt like a nice break from the robotic “sweater, jeans, repeat” formula forced upon me by the cold. And, all together, the layers were supremely comfortable and warm. Sometimes, in the effort of pushing an unordinary outfit of mine out the door, I can feel a little bit too “look at me!” in the dead of winter in my New England town, but this one felt actually pretty normal when I was bopping around running errands and walking the dog to my office. I also can see it working really well in March or April, when my outdoor coat isn’t fully covering it up.

A Dress Over Trousers

I’m constantly looking for more interesting “going out” looks for date nights or girls’ dinners that aren’t just a top and jeans, especially in the cooler months. One of my hacks is to add a touch of an unexpected texture, and, lately, that has been giving my crochet some airtime, even in the cold. I thought it would be fun to play with the sheerness of this ancient Zara dress (12 years strong!) over a very simple elastic-waist tapered trouser that I nabbed from a Margiela sample sale about 15 years ago.

I’m a little fatigued from an all-black look, and didn’t want to totally freeze, so I added a cream Ralph Lauren cashmere sweater tank from the RealReal and these super old Valentino lace-up ballet boots to bring a little more of a dancer off-duty vibe. This outfit was surprisingly comfortable and not as cumbersome as I imagined it would be. It feels like a refreshing, freezing-temps option that had me feeling fab instead of my usual winter drab.