How to Style Trousers: 10 Ways to Wear Work Pants Outside of the Office
Proof your most formal pants can add “errand runner” and “excellent dinner date” to their resume.
Back in January 2023, I professed my love to our Horton pants, which I’d recently begun to wear not only for work but also for farmers market runs, friend meet-ups, and a variety of other weekend activities. Now, over a year later, our collective obsession with wearing trousers as an everyday staple hasn’t gone anywhere; in fact, it’s only intensified.
It used to be that tops were the hero variable in our wardrobes, but in recent years, pants have gradually taken over, and for me, they’re often what makes or breaks an outfit. I’ve noticed that every single one of the women whose style I admire (e.g. Laurel Pantin and Harling Ross Anton) knows how to harness the power of a great pant—specifically a tailored trouser. That’s right: The chicest among us are out here rocking menswear-inspired silhouettes and suiting fabrics for work, weekend, and everything in between.
If you’re still of the mindset that trousers = workwear, just know that yours aren’t living up to their full potential. Case in point: The other week, I wore a black pleated pair to the Comedy Cellar, an NYC establishment that’s literally underground and serves mozzarella sticks in plastic baskets (a.k.a. the antithesis of formal). I think all of our pants deserve more nights on the town—and afternoons in the sun—so I’ve been documenting a wide range of outfits that make tailored trousers worth owning even if they never step foot in an office.
Scroll to see 10 non-worky ways to wear work pants, featuring three of my favorite styles: the Hortons, the Bias, and the Jordans.
Shop all the looks from this story here.
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How to Style Trousers
Meet the Horton Pant
With a high rise and an elegant flare, the Horton pants give you legs for days and instantly elevate any item in their vicinity. Most of our trousers include extra hem allowance—to accommodate a wide range of heights—so at 5’6”, I had mine hemmed a couple of inches. A word to the wise: When it comes to trousers, just assume you’re going to have to alter them in one way or another, and when you don’t, consider it a pleasant surprise. Far too many people see tailoring as a loss when really, it’s an investment. Besides, the Hortons are made from washable wool twill, so you’ll end up saving far more money on dry cleaning than you spent on alterations.
Look #1
Since the Hortons are fitted through the thigh, I like to balance them out with a looser style up top. The Leslie T-shirt is always a go-to; it isn’t oversized but does have that just-a-tad-relaxed cut I always want from my tees. I own it in five colors, but I picked the contrasting version for this outfit because I like how the collar ties back to the pants. To add some styling flair—and because it’s still sub-60° in NYC—I draped a cashmere sweater over my shoulders. My Converse high-tops keep the look balanced both in terms of color and casualness.
Look #2
You could wear the Horton pants with your college sweatshirt for a ready-in-seconds meeting-friends-for-brunch combination, but I prefer to pair tailored styles with pieces that are equally as comfy and slightly more elevated. Our Kim sweater fits the bill, as it’s slouchy and breathable (thanks to its 100%-cotton composition) but also features a refined dot pattern and contrasting trim. This look could easily become an office outfit with some slingbacks or loafers, so I dressed it down with my Adidas Sambas.
Look #3
Whenever I want to add instant edge or evening-readiness to a trouser outfit, I shrug on a leather jacket. Our Nicky jacket features a slightly cropped, tented silhouette that makes it more charming than grungy, so it still makes sense with a style as elegant as the Horton. I wanted to layer a bit more depth into this all-black look, so I went with the Axam turtleneck in kaleidoscope print as my underpinning. With its black background, smooth jersey, and fitted neck, the Axam retains the look’s sleekness, while the small-scale print adds visual texture. If you want an extra pop of color, you could add coordinating red flats, but I went with the sharp Lana boots for a more night-time vibe and added in the gold Valeria earrings for some shine.
Look #4
I was going to stick to three outfits per pant, but my Hortons have been around the longest, and I need to discuss how they’ve been my secret Saturday weapon for over a year now. On lazy weekend mornings, I used to automatically reach for sweats, but over time, an inverse relationship has developed between my energy level and the formality of the pants I put on. The lower my motivation to leave my apartment, the fancier my pants need to be in order to fool myself into feeling put-together. Admittedly, there are plenty of days I remain in my pajamas past noon, but once I do get moving, I’m often reaching for my Hortons, a soft, oversized shirt like this one from AYR (similar: Larissa top), a hat (instead of doing my hair), and my favorite old Reebok sneakers (similar: Everlane).
Meet the Bia Pant
When I first debuted the high-waisted Bia pants last fall, a super chic Englishwoman approached me on the street and simply had to know where I’d gotten my trousers. They’re one of those pieces. I know some of you are probably pleat-averse, but if you haven’t tried wearing them since the ‘80s, I encourage you to give them another go. I promise: They’re neither unflattering nor dated, especially when applied to wide-leg pants. The Bias feature a double pleat, which increases their gorgeous drape. As with the Hortons, I had mine hemmed two inches. These ones are also machine-washable.
Look #1
Since the double pleats of the Bia pants are a statement in and of themselves, I like to keep my top silhouettes relatively simple. Here, I paired them with a recently released version of our fan-favorite Leo top. Its polo-style neckline feels relaxed and looks dapper, while the new cotton-silk blend is polished, breathable, and most importantly, non-sheer. I bookended the look with a pair of ivory Mary Janes from Vagabond.
Look #2
One of my favorite things about spring (and fall) is that you can wear blazers as outerwear. Since the Bias are wide-legged, they look fantastic with fitted tops, but I’ve also started wearing them with my boxier blazers for a fully oversized silhouette. This navy one is from a secondhand shop, but you could go up a size in our Yiyan blazer for a similar look. I styled it with an old striped version of our Owen T-shirt (similar: our new signature stripe), and balanced out the preppiness with my Reebok sneakers (similar: Everlane). I really love the way their gum soles coordinate with the pants.
Look #3
I’ve been jamming to Cowboy Carter on repeat lately, which might explain why I had the sudden urge to dress down my saddle-colored trousers with the help of a denim button-down from AYR. I think the Bias look best with tops that don’t cover up their pleats, so I left the shirt open over my Sabine top. Made from our signature 365Knit, this thicker tank is the perfect springtime underpinning and pairs back to my white Birkenstocks, which I recently released from their winter hibernation.
Meet the Jordan Pant
Made from structured, super-smooth Italian ponte, the straight-leg Jordan pants are like sweatpants you can get away with wearing to work—meaning you can easily style them outside of the office, too. They’re pull-on, but the elastic waistband is discreet, and their wide legs feel freeing while reading effortlessly stylish. The front seams also lend a crisp, trouser-like look and elongate your silhouette in a really lovely way. Yes, you can toss these ones in the wash, too.
Look #1
Since the Jordans are sweatpant-adjacent, casualizing them comes easily. I like to counterbalance their smooth ponte fabric with a bit of visual texture and their muted ash hues with a pop of color. Here, I wore them with a graphic T-shirt from Imogene + Willie and a pair of cherry-red flats from Sam Edelman. Tip: I didn’t like the gold hardware on the flats, so I snipped it off and applied some super glue to the end of each string to ensure they won’t fray.
P.S. I was hesitant to get on board with the resurgence of ballet flats, but now I’m all in and especially love wearing them with full-length trousers. If you’re wondering what shoes go with each type of silhouette, check out our pants and shoes guide.
Look #2
On a recent drizzly Sunday, I had to catch up on a bunch of errands I’d been putting off, so I was craving an outfit that could both keep me cozy and withstand the unpredictability of a NYC day. The softness of the Jordan pants was calling my name, so I slipped them on and let them inspire the rest of my layered look. I went with the Larissa top, which provided a light, breathable base—ideal in the case that the weather took a turn—plus my new spring jacket, the Ness. I love the way the green complements the earthiness of the pants for a subtly springy palette.
Look #3
To be honest, it took me a couple of months before it even occurred to me that I could wear the Jordan pants past 8pm. There’s just something about stretchy, elastic-waist pants that sounds unsexy. As soon as I tried wearing them with the Lisey top, however, there was no stopping me and I’ve been experimenting with more zhushed-up looks ever since. Here, I paired them with a knit Cos vest for a balanced, waist-defining silhouette. To bring home the evening-y vibe, I added a pair of square-toed sandals I got from Miista a few years ago (similar: Ella sandals) and a set of sculptural Mejuri hoops.
