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Every so often, we're faced with some tricky fashion questions that have us wanting to phone a friend. Consider our column Ask an Expert that friend, turning to the experts — designers, stylists and other fashion professionals — to address your sartorial thoughts, comments and concerns.

It's safe to say a large majority of us gave our denim an extended break throughout a large chunk of the past two years. In many ways, 2021 was harder on us than 2020, and much like our lives have changed, our bodies and our wardrobes have, too. Shopping for denim can be a bit of a nightmare to begin with — add a global pandemic to the mix, and there's an entirely other set of challenges.

Most of our shopping has become even more online than it was before. Buying secondhand on the Internet, however, hasn't necessarily gotten easier. The biggest obstacle when it comes to finding vintage online is sizing, which is notoriously inconsistent in this category. Then, if you're looking at smaller e-commerce stores or individuals selling their thrifted goods, there isn't always the option for returns. Add in shipping lag times, and online shopping becomes a guessing game of when your items will actually arrive.

The benefits, however, are enticing. It's a more sustainable, and often more affordable choice. And there's nothing quite like the satisfaction of finding The Perfect Vintage Jeans.

Enter Alex Stevens, the owner of the New York-based vintage shop St. Evens and a deeply knowledgeable denim resource, who has developed a foolproof guide to finding your best pair of jeans without ever trying them on. (I'm 3-for-3 on vintage denim bought from her shop and on eBay using the guide.) We asked her to break down her biggest tips for buying vintage online — read them all, below.

Forget your size — and learn your measurements

"I feel like a lot of that typically turns into frustration with ourselves like something is wrong with us because those don't fit. At the end of the day, it's not about you or your body shape," Stevens says. "It's the fact that there are only 10 pants sizes, and those 10 exact sizes are supposed to every single person."

Because numeric sizing is so inconsistent — especially in denim — she won't look at the number on a tag. "I can wear a 2 in one brand and a 10 in another," she says. Shopping on sizing alone only adds to the frustration of finding the right fit, because there are quite a few measurements that go into that. You're better off working off of individual metrics: hips, waist (in terms of where you actually wear your pants rather than your natural waist), rise, inseam and length from waistband to ankle. (Men's denim nearly always comes with the waist and inseam measurements. If you're shopping for vintage women’s styles online, sellers will typically share the measurements; otherwise, you can ask for them.)

To begin, look through your own closet first. "For denim especially, but also for everything else, I recommend measuring your actual clothing and using that as a reference," Stevens says. This makes it so you know the measurements of the clothing you want to buy, not simply what your body measures.

Lay the garment flat, and measure from the top corner of one side of the waist to the other, not along the curve of the waistband. (Steves notes that you shouldn't pull the pants taut, but rather keep them relaxed.) Double that number, and you'll have the waist measurement.

For the hips, you'll want to measure at the widest point of the denim, between the waist and crotch or around the bottom of the zipper. Stevens' guide for St. Evens reads: "Think about how your body shifts as you move. Your hips and thighs spread when you sit, so make sure you have enough room that you can actually do things in your pants."

The inseam is measured from the crotch to the ankle, down the inside of the leg, while length is from the top of the waist down the outside of the ankle to the hem. Length minus inseam equals rise. The latter's important because you may not want your denim to fit at your natural waist: "If you aren't looking for something that's true high rise, you do need to know your waist measurement at a lower point," Stevens says.

Stevens recommends taking these measurements at least twice a year, since bodies change — however, you know your body best, and maybe more frequent measurements could be helpful. "It will give you a helpful range because you could have a pair of jeans you really love and realize they're really uncomfortable one week out of every month," she says.

Look closely at the fabric

Stretch denim versus non-stretch denim are very different, fit-wise and measurement-wise.

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"Traditionally, denim has always been 100% cotton, but during the '60s and '70s, there were some that had a little bit of polyester added to it," Stevens says, noting that synthetic fibers became more popular as "brands claimed it made it so the denim didn’t crease or wrinkle, and so that they were easier to take care of." Still, jeans didn't have that much stretch until the '80s and '90s — "then in the 2000s, we got a little crazy with it."

Older stretch denim is going to have a really small percentage of lycra or spandex, typically around 5%; anything you find with 20 to 50% of fibers outside of cotton are much more contemporary.

The stretch-versus-non-stretch debate really comes down to preference and what you consider comfortable: Stretch denim tends to have more give and offer a closer fit, but can be more challenging to shop for online and may require different laundering than 100% cotton denim. However, a little bit of stretch enables a pair of jeans to hold its original shape longer than its non-stretch counterparts.

Familiarize yourself with the brands

In her guide, Stevens offers suggestions as to which brands might work better for certain body types, based on her knowledge of the vintage market. (I've learned that Wranglers are a great option for me because they run long and narrow, and I'm 6' tall.)

She recommends Wrangler for a "narrower" body type or for someone looking for something more fitted: "When we talk about narrowness, we're saying that waist to hip measurement is closer – there's less of a difference between hip and waist," she says.

Lee might work well on hourglass shapes, since its jeans "tend to have a bigger waist-to-hip ratio and run a little curvier. They definitely have more shape in the waist and the butt than some other popular denim brands do." (Even if you don't have curves, they can create it for you, Stevens argues: "That excess volume can actually kind of create the illusion of having a little bit more in the hips and the butt, if that's something that you're looking for.")

Levi's are a good option if your body falls somewhere between a high waist hip ratio and a low one. "I think that's one of the reasons why Levi's have been so popular for such a long time — in terms of shape, they're very good for the middle," she says.

Visit your tailor

Stevens is a big supporter of tailoring our denim. ("It's probably cheaper and easier than you realize," she writes in her guide.) "The idea that we're all pulling the same clothing off the rack and that they're just going to fit everyone great is absurd," she says. "There are so many different body types, objectively, it's unrealistic."

If you're shopping with the intention of tailoring your denim, it's easier to size up than it is to size down. "If you flip any of your clothing inside out and actually look at the way that the garment is constructed, there's typically not going to be a lot of extra fabric with denim."

Hemming denim is the easiest fix, and doesn't typically affect the shape of the pants unless you're working with a specific leg shape, like flares. Then, how much you're shortening the pants comes into play.

"When it comes to alterations in the hips and the waist, I would say that two inches is probably the absolute max you're going to be able to alter them without significantly changing the shape and structure of the denim itself," Stevens says.

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