One Reader Asks: Am I Wearing the Wrong Jeans?

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A few days ago, I received an email from a reader with a question that I thought I’d address here for everyone’s benefit, since I can’t imagine he’s alone in his plight. The email in question:

Yo, I’m having an existential crisis about the jeans I wear right now. I’m 25 years old, and I just got my first real job as an associate teacher at a Manhattan private school. The dress code is casual, so jeans are allowed, but I don’t think mine look right, either at school or at the bar afterward. I’ve always worn pretty cheap stuff, usually in a light wash and a slim fit, which I’m realizing might be the problem. I’m 6’3” with an average build. Any suggestions? The $35 Target jeans aren’t doing it for me anymore.

Thanks,
[Name Redacted]

First, thanks for writing in. Second, some good news: I don’t think this is going to be as complicated or as costly as you fear it might be, and I applaud your hunch that the fit and the wash of your current jeans are an issue. From what you’ve described to me — light and slim — I’m picturing something a little too close to what you might see on one of the dolts in an episode of Love Island.

So let’s start with the fit. You’re gonna want to go wider, no question, which I realize can feel a bit daunting if you’ve opted for a true slim fit for a long time. But don’t worry: I’m not suggesting you get yourself into something ultra-wide and billowy, only that you commit to the baby step that is moving toward a straight fit. You’ll find some variation from retailer to retailer in what exactly a straight fit entails, but the defining characteristic across the board will be a minimal taper below the knee, culminating in a slightly wider leg opening. In my experience, the reason this shift can be somewhat jarring is that the wider leg opening impacts the way your jeans interact with your shoes. We get used to that view from above looking a certain way, and to see it change even slightly can make you feel like you’re wearing a costume. I get it. But I assure you, it looks totally normal to everyone else you’ll encounter.

As for the wash, conventional wisdom dictates that a darker color is more acceptable in professional or dressier situations. There are no doubt ways to class up a worn-in, lighter-wash pair of jeans, but my recommendation would be to start out all the way on the other end of the spectrum, with something raw or rinsed in a deep indigo shade. I’d also recommend checking out some black jeans, which are extremely versatile. From there, feel free to revisit your lighter washes — as long as you’ve got the fit right, they’ll work just fine.

And getting back to the fit for a moment, there’s really no way around this: you’re gonna have to try on lots of different pairs from lots of different places. Or maybe you won’t — maybe the first pair you try on will be the perfect Goldilocks situation. But you should know going in that no two straight fits are exactly alike. Some will have a higher rise than others (perhaps too high), which will impact the overall fit if you generally wear your jeans closer to your hips than your natural waist. Some will be a little wider in the seat and thighs. Hell, a 32” waist from one brand might be a 35” from another. Given that these sizes are ostensibly actual measurements in inches, this should not be the case, but alas. The universe is an imperfect place.

Finally, let’s talk about prices. I don’t imagine you’re looking to go from $35 Target jeans all the way up to this impeccably broken-in $400 pair from RRL, and that’s perfectly fine. There’s a wide range of affordably priced denim, between, say, $60 and $150, out there for the taking — especially at this particular moment, when every retailer on earth is having holiday sales.

So where should you start your search? I’d say you start with the classic Levi’s 501 and branch out from there. I’ve gone on record as a fan of Madewell’s 1991 line. I think J.Crew’s 770 fit would work well for lots of people. Uniqlo is probably worth a look, as is Abercrombie and Everlane. I’ll drop a more complete list below, but remember, the first step was recognizing that you have a problem. So congrats, and good luck in your journey.

If anyone else has a style-related questions, drop a line, and if I can’t answer it myself, I’ll find someone on staff who can.