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A Beginner's Guide to Buying the Right Pair of Jeans

In the market for some good denim? We asked an expert, 3sixteen's Andrew Chen, for some pointers to make sure you're finding the right pair for you.

There are plenty of important things to consider when buying the right pair of jeans. 3sixteen founder Andrew Chen provides some of his pointers for buying premium denim.
Dan Chen

Key Takeaways

  • Andrew Chen of 3sixteen provides some key tips and tricks for any beginner’s in the market to buy premium jeans that age well.
  • He recommends denim-focused brands like Sugar Cane, 3sixteen, and Iron Heart over luxury fashion labels, suggests budgeting around $200–$400, and says Japanese denim is an excellent but not mandatory starting point. He also suggests learning to measure your current pairs and dialing in your preferred fit, rise, and leg opening.
  • Chen also provides some pointers for upkeep, longevity, exploring vintage, and more.

Jeans are a staple in any closet. Almost every brands makes them. They are accessible at any price point and can fit into any style. But when it comes to getting the right pair of premium denim that will last you for years, there are some things that you need to consider before making your purchase.

Not everyone is a denim expert. So, we asked someone who is. 3sixteen founder Andrew Chen is a veteran in the denim game. Chen started the brand in 2003, but didn’t release its first pair of cut-and-sew jeans until 2008. Nowadays, the New York-based label has become one of the go-to brands for premium denim. Chen is also a partner in the New York outpost of Self Edge, a premier destination for high quality denim with outposts in New York, Los Angeles, San Francisco, Austin, Portland, and Mexico.

“Generally speaking, everything that you have will lose value as soon as you drive it off the lot. Unless it's a future collector's car, there's depreciation immediately,” said Chen. “Most clothes, the more that you wear them, start to fall apart. But jeans get better the more that you use them.”

From brand recommendations to budgeting tips, check out some of Chen’s biggest pointers below.

Shop the Denim Collection on Complex.

How Do I Find the Right Size?

Andrew Says: “Number one thing everyone needs to learn how to do is learn how to measure their garments. If you are able to measure your jeans, the ones that you own, then now you at least can figure out what you like and don't like about them.

“You want to learn how to measure a leg opening, an inseam, how long the jeans are. We have a guide that we put together just to teach people this because once you have a baseline of being able to measure your garment, now you can go out and you can compare. A lot of online retailers have jean finders. You can plug in the measurements that you like and they'll find stuff for you that fits you well.

“A seasoned professional who understands how jeans fit, how they break in, how they stretch, how they shrink can really walk a customer through those different aspects of jeans, but it all starts out with personal preference of what you feel comfortable in.”

What Fit and Wash Should I Buy?

Andrew Says: "Oftentimes, when we're sizing people at our stores, I start with what they come in wearing. I ask them, ‘Do you like what you have on?’ It comes across very quickly whether they feel good in them or not. And then we start to dissect that. Is it too slim in the thigh? Do they not like where it sits on their waist? It all starts out with personal preference of what you feel comfortable in.

“If you've settle on a jean that you're into, you can just Google search what it looks like faded. Everybody wears in jeans differently, but at least it gives you an idea of where it goes.”

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What Brands Should I Check Out First?

Andrew Says: “Generally speaking, I find that brands that specialize in denim are going to just have a lot more experience with making a pair that lasts a long time, that's constructed the right way with quality hardware, sewn using the right machines. If you're buying jeans from a brand that doesn't specialize in denim, like a fashion brand, it's not their priority. I'm not saying that a fashion brand can't make good jeans, but I would take a jean from a jean brand any day.

“A pretty accessible first pair of jeans would be from Sugar Cane. I would take a look at them. They make a lot of modern and heritage-inspired fits. You can find a historically accurate Levi's reproduction from them, or you could also find a really nice lightweight slim straight jean as well.

“I love what we do [at 3sixteen], obviously. I think that we are the kind of brand that you come to for modern fits with an eye towards the way jeans were supposed to be made. So we have heritage in the construction, but the fits are modern.

“And then I would look at Iron Heart, for just sheer weight and what can be accomplished through denim. A lot of people have never felt something as heavy or as overbuilt as Iron Heart. It's kind of like the G-Wagon of jeans.”

Do I Need to Try Them On?

Andrew Says: “Go to a specialty denim shop, browse it in person, touch stuff, put it on. These are in-person services that you just can't replace, and there's no AI chatbot that's going to be able to explain it to you.”

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How Much Money Do I Need to Spend?

Andrew Says: “If you're buying it from a luxury house, typically it's too much for what it is. There's diminishing returns to scale.

“Now, do specialty Japanese brands have $500, $600 pairs of jeans? Yes, but that's not the norm. Generally speaking, you're going to get a world-class jean for $200 to $400, and there's no need to spend above that.

“I do want to clarify that lower priced garments have a place in the ecosystem. I understand that not everybody can afford what we make or what other Japanese brands make. But for me, I would much rather buy something once and enjoy it for a long time and have something that I'm really happy with and proud of at the end of it. I think that people learn this on their own when they buy something and are disappointed with it six months in.”

Is Raw Selvedge Denim From Japan the Only Way to Go?

Andrew Says: “No, but Japan is putting out, I believe, the best fabric in the world. It doesn't need to be raw. It doesn't need to be selvedge. It doesn't need to be from Japan to be a high quality pair of jeans, but it's such a great starting point. You're already halfway there if you are finding something from Japan. There's such a deep appreciation of craft and textiles from Japan to where it just results in a really beautiful product. So I would start there.”

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Do My Jeans Need to Be Heavy?

Andrew Says: “Weight is not the only signifier of longevity and quality.

“A lot of it has to do with care and maintenance. If you don't wash your jeans and just wear them for a year or two, then it doesn't matter how well they're made, they're going to just start falling apart. But people often like jeans that are heavy because older customers are like, ‘Oh, this is the way that jeans used to be made.’ Newer customers are just like, ‘I've never felt anything like this before. I didn't know that denim could be made this way.’

“And typically, heavier fabric is harder to work with. You need to tune your machines to be able to sew it correctly. So, it doesn't mean that the product itself is better, but what it says to you is that the brand made a conscious effort to source something that's more expensive. And so usually you're going to end up with something better.”

Once I Buy Them, How Often Do I Need to Wash My Jeans?

Andrew Says: “I wouldn't wash them as often as I do socks and underwear. They don't have to be washed after every wear, but consistent washing helps to preserve the life of the jean and keep it on the road for longer. Jeans that aren't washed often people think that they get this really beautiful fade. And what's happening is the dirt gets embedded in the fibers and then it starts to wear on the jean almost like sandpaper. People get premature rips in the knees or in the crotch or whatever.

"And also it just smells bad. It's not fun to be around. So for hygiene purposes, for longevity purposes, we recommend washing them when they feel dirty. So in the summertime, that could be once every two weeks. In the wintertime, it could be once every one or two months.

“I always cold wash my jeans and hang them up to dry. Dryers are just not good for clothes overall. Anything that I care about, I usually hang to dry. I don’t ever dry clean jeans.”

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Should I Tailor My Jeans?

Andrew Says: “Yeah, I shorten them all the time. I only tailor my jeans by shortening them to the length that I want. I don't change anything else about the fit of jeans. I think that if someone needs to change the fit of their jeans, they’re probably in the wrong cut or fit of jean. Jeans were sewn on factory machines. If you're taking them apart and putting them back together, they're not going to be as strong as how they were originally.”

What About Vintage Denim?

Andrew Says: “I think [vintage] is great, but what's hard about that is you just have to be really, really patient because you can't get a full size run in it. It's just whatever's at the store that day. But yeah, it's something that everybody should try if they have the patience for it.

“All the classic American brands have made good jeans over the years, but they all kind of had their own look to them. A lot of people over the past years have been really into Wrangler cowboy cuts because they like a tighter top with a little bit of flare from the knee down. But five, six years ago, nobody's really checking for them.”

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