The only New York jeans worth buying (and the ones that are total scams)

I once spent $290 on a pair of raw denim jeans at a shop in Soho—I won’t name names yet—and proceeded to have the worst night of my life. It was 2017. I was meeting a date at a dive in Greenpoint, and I had decided this was the night to ‘break them in.’ Big mistake. By the time the second round of drinks came, the fabric was cutting into my hips so badly I couldn’t actually reach into my front pocket to grab my wallet. I had to stand up, awkwardly shimmy my hips like I was doing a low-speed hula hoop, just to pay for two Negronis. I looked like a lunatic. The date didn’t lead to a second one, and I walked to the G train with actual bruises on my iliac crest. Raw denim is supposed to be a journey, but sometimes the journey just sucks.

Most people writing about New York jeans brands are just regurgitating press releases. They haven’t actually bled into the waistband of a pair of 14.5oz Japanese selvedge on a humid July afternoon in the subway. I have. If you’re looking for ‘versatile staples for the modern man,’ go read a magazine. If you want to know which local brands actually make stuff that justifies the obscene rent they pay for their storefronts, keep reading.

3sixteen is the only hill I’m willing to die on

If you live in this city and you care about clothes, you eventually end up at 3sixteen. They started here, they’re still headquartered here, and they haven’t sold their soul to a private equity firm yet. I’ve owned three pairs of their Shadow Selvedge. I might be wrong about this, but I honestly think the way the indigo fades into that weird, electric blue is better than anything coming out of the high-end Japanese mills directly.

I tracked my last pair. I wore them for 412 days before the first wash. I know, that’s disgusting. My girlfriend at the time made me keep them in a freezer bag for a week because she said they smelled like ‘stale subway air and regret.’ But after that first soak in a bathtub? Perfection. The crotch finally blew out at month 14, which is a specific data point I’ve noticed across three different pairs of their ST-120x fit. It’s like a built-in expiration date. But I don’t even care. I just took them to a guy in the Lower East Side to get them darning-stitched and kept going.

The Shadow Selvedge is basically a cast for your legs that eventually turns into pajamas. It takes six months of misery to get there.

Anyway, I’m getting off track. The point is that 3sixteen feels like a New York brand because it’s tough and slightly unforgiving. It doesn’t apologize for being stiff. It’s the antithesis of that stretchy, spandex-infused garbage you find at the mall. Buy them once.

The Knickerbocker problem (and why I changed my mind)

I used to think Knickerbocker was just for guys who wanted to look like they worked on a 1940s shipyard but actually just work in ‘brand strategy.’ I hated the aesthetic. It felt performative. What I mean is—actually, let me put it differently. I thought they were all costume and no substance.

I was completely wrong.

I bought their standard denim on a whim because I needed something that wasn’t as skinny as my 3sixteens. The rise is higher. It actually lets you breathe. I wore them to a wedding in upstate New York last October and didn’t feel like I was wearing a costume. I felt like a person. They use a 12oz denim that’s surprisingly light but doesn’t feel cheap. It’s the kind of pair you can actually wear to a nice dinner without looking like you’re trying too hard to be ‘rugged.’

I’m going to be mean about Rag & Bone for a second

I know people will disagree with me here, and they’ll point to the ‘heritage’ or whatever, but Rag & Bone has become the official uniform of the guy who just moved to Murray Hill and wants to look ‘edgy’ for his parents. They’re airport mall clothes now. The quality has plummeted over the last five years while the prices stayed in the stratosphere. If I see one more pair of ‘distressed’ jeans that look like they were attacked by a very specific, very artistic sandpaper machine, I’m going to lose it. It’s fake. It’s unearned. Total lie.

The high-fashion trap on Elizabeth Street

There are a dozen other brands tucked into storefronts between Soho and Nolita. You’ve got places like 45R where a pair of jeans costs $600. I once spent forty-five minutes in there just touching the fabric. It felt like it was woven by angels. But let’s be real: nobody needs $600 jeans. I don’t care how many ‘natural indigo’ dips they did in a fermented vat in Okayama. At that price point, you aren’t buying pants; you’re buying a personality because you don’t have one of your own.

I actively tell my friends to avoid the ‘designer’ denim labels that pop up every season. They usually disappear in two years anyway. Stick to the shops that have been here. Self Edge on Orchard Street is still the mecca for a reason. They don’t stock junk. If they carry a brand, it’s because the construction is actually solid. I once saw a guy in there trying to return a pair of jeans because the button fell off after a week. The staff didn’t even argue; they just fixed it on the spot. That’s New York. Not the shiny windows on 5th Ave.

I still have that pair of bruised-hip jeans in the back of my closet. I can’t bring myself to throw them away, even though they represent a failed date and a lot of physical pain. Maybe I’m waiting for the day I magically lose two inches off my waist, or maybe I just like having a reminder that ‘premium’ doesn’t always mean ‘better.’

Why do we even care this much about indigo-dyed cotton? I honestly don’t know. It’s a lot of money and effort for something that mostly just makes your legs blue for the first month.

Go to 3sixteen. Get the Shadow Selvedge. Prepare to suffer. It’s worth every penny.