How to Wear Cargo Pants With Your Tiny Shirts

We are in an era when the big-pants, little-shirt combo reigns supreme. And for that, we have to thank our ’90s/Y2K-aesthetic founding mothers: Aaliyah, Christina Aguilera, and Jennifer Affleck (née Lopez).

The big pant du jour occupying the closets of many a New York City baddie and their dads alike? Cargo pants. Definition: “loose-fitting casual slacks with large patch pockets on the thighs.” But for me, cargo pants are defined as such: any pant, many pockets.

I bought my first pair this past winter at L Train Vintage in the East Village from Little Donkey Andy. It’s safe to say these babies have never seen a hike while being worn on my body, but they have been the object of envy at many cafés throughout the city. They fit me like a glove, are incredibly insulated, and make my butt look like a set of perfectly inflated balloons. I usually pair them with a plain cropped shirt and platform boots.

I had long been a cargo pant/cargo short hater. I thought they were ugly. I had no excuse. They’re practical with their plethora of pockets for storage, comfortable thanks to their loose fit, and nostalgic in the way they remind me of my father (a nice thing for some people, bad for others).

At some point over the past year, I developed taste and became a believer in the cargo pant. Or perhaps I got tired of my fingers and hands being sore because for years we women and femmes have rightfully complained about the lack of pockets in our clothing and rejoiced when stylish articles contained them: “Look! It has pockets!” As a result, we have become increasingly adept at holding 8 million things in our precious hands (think: that one photo of Dakota Johnson holding two coffees, her phone, her wallet, a set of keys, a bag of food, and some other unidentified beverage all in her bare hands). Never again! Instead, thanks to our collective newfound love of cargo pants, we will have far too many pockets to fill and hands that are free for more important things, like holding someone else’s or making ceramics.

India Roby, a fashion writer at Nylonloves the phenomenon because of the roominess: “I think people are into the cargo-pants trend because no one wants to feel restricted, whether that’s physically with clothes, especially since it’s so hot outside, or even in other aspects in life.” When she feels like jazzing things up, she usually pairs her favorite ones from Hollister with a blouse and a pair of platform shoes.

My personal preference for cargo pants is that they should, if possible, be secondhand. With cyclical, nostalgia-adjacent trends like this, quality pieces are likely already in circulation at your local thrift stores and on Etsy, Depop, thredUP, or Poshmark. If you’re looking to cast your net a little wider, below are some options we stand by.

I have never laid my eyes on a pair of cargo pants more beautiful than these. Our beauty writer, Asia Milia Ware, recommended these to me, and I would do anything (almost) to own a pair.

These are fun and funky, as is customary with Collina Strada, and are made entirely of cotton. Comfort and chaos! We love to see it.

Yes, these come only in black but are statement-making due to their taffeta material. Imagine how mesmerizing these would look in motion.

These are bound to get you attention simply because of how utterly massive they are. The bigger the pant, the bigger the icon.

From Maison Margiela and on extreme markdown: 100 percent cotton and an elastic waistband. I’m not sure it gets better, or chicer, than that.

Another markdown goodie coming at you by way of Isabel Marant, recommended to me by senior writer Sangeeta Singh-Kurtz, who just purchased these because she likes to “dress exclusively like Lara Croft.” Don’t we all?

A beautiful marriage of the wide-leg, tailored trouser trend and a cargo pant.

Our shopping writer Chinea Rodriguez opts for this set with an adjustable waist and cuffs, calling it the “perfect oversize fit.”

What you see is what you get with these pants, a favorite of shopping editor Bianca Nieves, who wore them so much that she left them at the laundromat by accident. (If anyone finds them, do the right thing and contact her.)

Our deputy style editor, Joanna Nikas, opts for these from Dave’s New York. They have an adjustable waist and cuff, which we love, and are likely heavy-duty enough to last you through an apocalypse.

This is the pair that started it all for me. They’re waterproof as heck, but thanks to the heavier material, I’d recommend saving them for colder weather.

The big-pant agenda in action.

I just know I could climb a rock wall, mountain, or very steep set of stairs no problem in this pair.

Beauty editor at Elle Margaux Anbouba swears by these waterproof, Kim Possible–esque pants. “I wear them out when it’s raining with my dress or outfit underneath,” she said, “and take them off in the bar because they fold up super-small.”

I would wear these to the movies every single time: 100 percent cotton and multiple pockets that are ready to be stuffed with snacks to sneak in.