How to Find the Pair of Vintage Levi's Jeans That Fit You Best

Kirstin Sinclair/Getty; Embroidery by LaughingWife

It seems as though everyone I know is currently obsessed with vintage jeans. Myself included. It's all I want to wear, and it's the only thing I want to buy—something easier said than done, which I didn't learn until I was in the fitting room at a vintage pop-up shop in SoHo trying on what seemed like my 50th pair. It was a disheartening process and the search seemed futile—so much so that at one point the shop's denim expert began to avoid eye contact and hint at what I suspected 25 pairs ago: "We might not have anything for you."

Of course, it wasn't her fault. I had given her very strict parameters to work within: only vintage Levi's 501s, a fit that wasn't too tight nor too baggy, and a wash that was neither too dark nor too light, but had that medium, faded "vintage-y" coloring. Instead, I tried on pairs with mysterious stains along the back and sides, some that were too dark, others too light, jeans that were baggy in the butt or poofy in the front. In a last ditch effort, she asked me if I wanted to try the 505—a style that's very similar to the 501s in almost every aspect except that it has a zipper fly instead of buttons. Sure. And they were perfect. My butt was perkier, it was both straight-leg and snug, and there were these cool faded lines—scars from years of wear from another life, but nothing icky.

I may have lucked out as Goldilocks with my "just right" jeans, but it struck me just how much of a challenge it is to shop for vintage denim. All of them run small by several sizes, and if I had been left to my own devices, I would have been at a complete loss. Why are vintage jeans so small? Why are no two pairs alike? Why is vintage denim shopping so damn difficult? To get to the bottom of this, I chatted with Karyn Hillman, Levi's Chief Product Officer, and Jonathan Cheung, Levi's Head of Design, for some answers, which inevitably led to a comprehensive step-by-step guide on how to find the right vintage jeans for you.

Adjust Your Expectations

"Carve out some time, and know that it's going to take you awhile to find the perfect pair of vintage Levi's," Cheung says. "You might try on, say 20 pairs, but enjoy the experience, enjoy the journey. It can get really addictive once you find one."

Judging from my personal experience, I can wholeheartedly attest to that. But why is each pair so different? A lot of it can be attributed to its past life. "Denim is a living, breathing fabric—it molds and takes the shape of the previous owner's body, like physical attributes—their waist, hips, and knees—or their lifestyle choices," Hillman says. "You can argue that that they're all one-of-a-kind for that reason alone."

Another reason that's specific to the 501, is that the style was cut from a shrink-to-fit fabric, or raw denim. That means a newly purchased pair of 501s from back in the day would have shrunk down to fit the owner's body once it touched water. "Each pair of 501s is very individualized; it also depends on how the previous owner was washing them—they could have been stretched out, or shrunken down if they were washed in super hot water," Cheung explains. "You definitely go on a journey with the previous owner."

Don't Get Hung Up On Sizing

Throw everything you know about sizing out the window. Vintage sizing on its own is tricky, but vintage Levi's sizing is especially tricky. "There's vanity sizing (an industry-wide practice of assigning smaller sizes to boost sales), which means the marked size of your jeans today is actually smaller than your true waist size," Cheung says of how things are sized today. "Vintage Levi's denim fits differently because it's based on a men's fit. The 501s and 505s were designed with a 'true to size' fit for men and their waists, who used to wear their jeans that high up in those days."

Because of both factors—vanity sizing and men's fits—it's a little harder to pinpoint your size in vintage denim. The general rule of thumb though, Hillman says, is to go two sizes up (so if you're a size 27 in contemporary women's sizing, then you're a 29 in men's vintage Levi's).

Again, because no two pairs of 501s are alike, it's still important to try each one on. However, Cheung says that 505s are more consistent in their fits because they were cut from a pre-shrunk material. But contrary to what you might think, they're not looser in fit. In fact, they fit tighter, more snug, which means you might consider sizing up one more.

Women's 501s, though, were introduced in 1981, and if you find vintage women's cuts of the 501, their sizes are fairly comparable to today's sizing (so if you're a 27 in contemporary sizing, then you're a 27 in women's vintage Levi's). Not sure how you can tell the difference between men's and women's vintage 501s? "The women's rise is much lower," Cheung says. "The J stitch—the stitch where the button fly is—is substantially shorter, and it's why we lengthened it for the current women's 501s that you can buy in stores now, to make it more like the vintage men's 501."

Know Your Numbers, and What They Mean

We've thrown out numbers like 501 and 505, which, by now, you know are the Holy Grail of vintage Levi's jeans. The three most popular vintage styles are the 501, 505, and 517, Hillman confirms. You can find it stamped on the leather patch on the back or on the tag inside. All three were originally designed for men, they're all extremely flattering on the butt, and they're all coveted. Yet, each one is slightly different.

The 501: Introduced in the 1890s, the 501s are the original "anti-fit" jeans from Levi's. They have a mid-high rise with a button fly.

The 505: The zip-fly version of the 501s with a slim straight leg that launched in the 1960s.

The 517: A zip-fly style inspired by the 505s with a boot-cut silhouette, which were originally designed to be a "cowboy jean."

And if you come across a 606 with an orange Levi's tab, then you're in luck—you found a rare, collectible item. Cheung says the 606 was one of the first slim jeans that Levi's ever made and are incredibly flattering.

Which Style Will Flatter Your Shape? 

To make things even more complicated, the vintage men's 501s, 505s, and 517s have gone through gradual and continual changes with each passing decade. There are popular, well-known ways to figure out when they were created, like if the red Levi's tab on the back has a big E, then it was created before the '70s, or if there are "care tags," which weren't added until the 1970s, or if the stitching on the inseam is single or double (if it's single, then it was made before the mid-1980s). So which one is best for you?

If you're an hourglass shape: You want to look for an older pair (any jean until the mid '90s), because they tend to be more nipped in at the waist. "It's really because as you go back deeper into history, men wore their jeans higher up, closer to their belly buttons," Cheung says. "The leg, too, was relatively slim in the '60s."

If you're rectangular: Search for a pair that was made in the mid- to late-'90s. "As men started started wearing their jeans toward their hips, due to rock 'n roll influences (Ramones, Iggy Pop, Kurt Cobain), the 501s evolved into a looser, more relaxed, more grunge-y shape," Cheung continues. "That's why the modern ones are cut a little squarer and rectangular on top, and have a wider leg."

If you're rounder in the tummy: The 505s are probably the most flattering on you. Because the 505 has a zipper fly, versus a button fly on the 501s, it lies flat on your midsection. "The buttons on the 501 push the front of the tummy out, creating a pouch," Cheung explains. "The zipper fly makes that area flat and holds you in."

If you're looking for a universally flattering cut: Then it's the 517s for you. The high-waist boot-cut style flatters everyone—crop them at the ankle to DIY a kick-flare silhouette or leave them long for a leg-lengthening effect. (Fun facts: The 517s were style icon Carolyn Bessette-Kennedy's preferred jean, and currently, they're very popular in Japan.)

Study the Shape

Got all that? When you're in the store, the easiest way to tell if the jean fit will flatter you is to, well, study it. Yes, it's that simple. "I literally hold it up, belt loop to belt loop and see the actual shape," Hillman says on her vintage denim shopping strategy. "By staring at it, you can tell if it's nipped in at the top or if it runs straight up and down, and know if it'll flatter your figure."

Do the Neck Test

If a jean is stripped free of tags or patches to denote its size and style, then do the neck test. "If I don't have a tape measure and I don't want to rely on the sizing, then I'll throw the jean around my neck—​if it fits, then I know it'll fit over my hips and waist," Hillman reveals. "I do this test a lot, especially if I can't be bothered to try on a style."

Make Sure It Fits from the Butt Up (You Can Tailor the Rest)

"Everything from the waist to the top of your thighs is critical," says Cheung, who personally gets his Levi's altered at any one of Levi's Tailor Shop locations. "You need to get that fit right, because you can tailor the length and the width of the leg, otherwise you'll have to reconstruct the entire jean."

Some insist that you must keep the original hem in order to maintain the jean's resale value, but Cheung says that that shouldn't be a priority. "It's more important to get the length you feel comfortable with, because someone 10 years later will appreciate it," he says. "Sometimes that even increases the value, especially with jeans are highly personable. It's all part of the journey."