I stood next to a man on the Broad Street line last week who wore pants so cavernous around the ankle that they appeared to be hanging off a store hanger. They weren’t slim. They weren’t straight. Hell, they barely qualified as what I’d call relaxed—they were full-on voluminous. I saw enough thigh to remember his pants were there despite plenty of pant-leg lying around his boots like an ungainly parachute. My immediate thought was “did he snag those from someone else’s closet.” About four seconds later, my second thought was I’d already spotted three other guys that week who wore almost the exact same outfit, style-wise, and it never occurred to me it was a trend until I saw this guy’s massive pants.
I’ve been thinking about whether men’s baggy pants are making a comeback ever since.

If you’re looking for me to put that question to rest right here in the opening section, I’m afraid you’ll be disappointed. There’s no definitive yes or no answer to that question, because the truth is it depends on what part of town you live in and who you’re reading this article next to. What I can do for you is explain what I’m seeing out and about myself. Because more than anything I want to distinguish between what’s happening on the streets and what’s happening on runways. Actual people wearing clothes in climates that match ours as opposed to what some designer thinks we should be wearing while standing on plywood atop what’s vaguely suggestive of a downtown Manhattan street.
On streets, not runways
The thing that no one wants to acknowledge whenever this conversation heats up online is that when someone bookmarks a fashion article to prove their theory months or years later, what they’re really doing is finding a middle ground to justify their initial stance. People see one photo from fashion week of a guy in pants so baggy they could double as shorts, no gap style, and scream “SEE I TOLD YOU SO baggy jeans are back!” Sure, if you want to say they’re “back.” But they weren’t ever gone if you were paying attention to your local bars, concerts, and restaurants, not to mention high school—where teenage boys have been slopping around in relaxed-fit jeans since the day they were invented.
I love clothes. I will happily spend all day thinking and reading about clothes, which is why I end up with a paycheck from doing so. But I also pay attention to stuff in my own life—I shop for clothes, I own clothes, I wear clothes practically every day regardless of whether I’m going somewhere fun or just turning antennas at my desk. And what I’m seeing isn’t-that-big pants.
What I’m seeing is slightly more room than we’re used to seeing at the waist and thigh. Nothing so voluminous that your dad would wear them thinking they’re biking shorts in disguise, but something noticeably slouchier than your standard slim fit.
I have a buddy named Dallas who works in retail at a menswear store in Fishtown. He told me a couple of customers who came in routinely buying skinny jeans a size too small have recently asked for the same brand in sizes larger than they were previously buying. And they weren’t doing it to lose the tags. They wanted the extra space.
I know what you’re thinking. Wait, wasn’t that kinda the thing ten years ago? Yes and no. See the difference between what’s happening now versus what happened then is all about how we classify certain words. Skinny jeans aren’t skin tight anymore, which means “skinny” now applies to anything that comes anywhere near your natural leg line. And what I’m seeing myself, and what Dallas is telling me he’s seeing represent a shift away from that skin tight towards something slightly more roomy but not nearly as … ahem … roomy as it was a decade ago.
Me trying not to sound like I got this wrong before
I’ll own my flaw in all of this right now. About two years ago I bought a pair of wide leg trousers because I saw someone wear them that looked unreal and assumed their outfit would recreate itself on me as well. It did not.

I’m 5’9 and those, what were intended to be high fashion on a 6’2 dude with hip pockets that wouldn’t giggle fell somewhere between “I don’t own any other pants” and “people who do laundry.” My ankles swayed in fabric like I was proposing to my jeans instead of the other way around.
The difference between then and now is that I know how to actually wear them. Which is not super goddamn baggy all over. Allow me to explain. If you’re wearing a baggy waist, you gotta give somewhere else some shape or you’re just wearing a sack with straps. I’ve seen guys pull it off—and that subway dude was one of them—but they always have something tight/cinched/close fitting to balance out all that loose fabric. Be it a fitted t-shirt, a jacket that isn’t boyfriend style, or even just a slim tie to offset a baggy sweater.
I also learned that in order to actually pull off full-on baggy pants you gotta commit. Don’t try it with shorts stuck in your thighs unless you’re going for a look I can’t even describe to you right now because I don’t know how comfortable you are with naked ankles. But if you’re going to wear them, own it..land full-on commit and get yourself a pair of baggy pants.
Ryan is a Nottingham resale obsessive who hunts secondhand trainers and streetwear, and can tell you which app, which search term and roughly which hour a good listing drops. He also knows how to check a pair is genuine.



