I'm a Recent Cargo Pants Convert—How I'm Wearing Them This Winter
I tried them out in a few different scenarios, and, I have to say: I’m hooked.
There comes a time in every New Englander’s life when a canvas utility pant becomes a necessary piece of your wardrobe. For me, this happened to coincide with a moment when we, as a collective, are basking in a ‘00s revival—which means I have been casually searching for a pair of cargo pants that can carry me through several seasons.
The secondhand market is usually my first stop, especially for a nostalgic piece boomeranging back into the present day. I had a few boxes I wanted my cargos to tick: baggy but long; not cropped; no cinching at the bottom; a bold statement pocket; beige or tan. I felt strongly like this could be a job for Ralph Lauren, but could not find a vintage pair in a more winter-friendly weight. I also considered Sanctuary, recalling that the brand was a cargo pant authority when I worked at a boutique in the early ‘00s during high school. (Bonus: ThredUp has a huge selection.) But none were quite exactly what I was looking for. I had to venture out into new arrivals.
I didn’t want to commit to anything super expensive, in case these didn’t feel quite “me”. One of the New England girlies’ go-tos in this category are Rudy Jude’s utility pants, but I think I need to work up to them. (I’m not that “utility” quite yet, and they didn’t really have the big pocket vibe I was craving.) In the meantime, I thought Free People could definitely have the baggy silhouette I was looking for in cotton twill—and I was correct!
The Brentwood Slouch Pants give off a Carhartt-meets-Isabel-Marant vibe with a slightly tapered leg. As one of my favorite memes says, “Everyone wants to wear Carhartt until it's time to do Carhartt shit,” and I certainly am not, so these fashionized versions are much more in my wheel house.
I’ve already worn these cargo pants quite a bit in what turned out to be a late winter tundra effect. They’re warm, durable, and a little more “fashun” than a pair of jeans, which helps pull a look together when we’re stuck in 20º weather for weeks on end. I tried them out in a few different scenarios, and, I have to say: I’m hooked.
Wearing Cargos at Work
I loved trying these out on set for a shoot I was styling. I luckily was able to bring a change of footwear for a more “indoor” look away from the two feet of snow ruining my outfits. I did some light colorblocking, drawing from some Spring 2026 styling inspiration with a navy wool blazer and light blue sweater vest layered over a pale yellow turtleneck. A pointed-toe, shearing-trimmed boot looked great with the tapered leg of the cargo pant. I popped on a cheery yellow faux flower, too, because, why not? 10/10, would wear again.
Wearing Cargos on a Date
What I had intended to wear on a date night that unfortunately fell apart thanks to a snowstorm and some seasonal germs sadly only got as far as my living room. But the vibes were right! Because I literally cannot stop wearing a turtleneck under everything this time of year, I opted for a fitted cashmere version with raw hems under my trusty crochet top from Diotima for a playful texture in an attempt to “dress up” in a deep freeze. I can see me wearing this combo again with just a bandeau top come summertime. I love these old Celine boots with the square toe as well, proving that the length of the pants can indeed accommodate a heel and not lose that “coolness” I was craving with a baggy shape.
Wearing Cargos to be Cozy with Friends
I walked over in the snow to my friend Kelly’s, who lives nearby, for a cozy sushi dinner night with gal pals. I was bummed I didn’t pack my tan Birkenstock clogs for the intent of documenting this ‘fit, but I knew I would end up in cozy socks for our hang anyway. These sturdy Uggs I received earlier in the season are now sold out, but they have served me well in this snow.
Aside from these technical details, I loved the cargo with a cozy nordic-type knit. It felt like an effortless combo that I will be sure to tap into for the rest of winter and perhaps a future ski trip—Birkenstock clogs included.
Wearing Cargos for Momming
On a particularly freezing day, I was determined to feel some kind of springy-ness, which meant including some color in my outfit—even if that outfit just went as far as the library with my son. I can still dress for the other moms!
My most cheerful floral Miu Miu sweater and Damson Madder knit hood were an unstoppable combo against my black shearing coat and black Ugg snowboots. The cargos in their tan also played into the contrast that pulled the whole thing together and grounded it in reality. I will definitely replay this one in springtime.
