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A First-Rate Guide to Buying Second-Hand Clothes

Here’s how to tell legitimate grails from what’s just plain old

Vintage stores can feel like textile wastelands — endless rows of clothes with tiny histories. Some of them can be weird. Others can be gross. Almost all of their wares will emit a distinctive odor. Moreover, when inside, you have to be patient and willing to fail — very much okay with the fact that you may not find anything you’re looking for. Still, I’ve found some of my most prized possessions within them.

It helps too that buying vintage is the only half-decent way to be sustainable. Sure, fast-fashion brands like H&M have their “Conscious” lines, clothes that are ostensibly made up of “more sustainable materials, like organic cotton or recycled polyester.” But they also churn out 500 new designs per week. Which is to say, if you want to be genuinely conscious of your environmental footprint, you either need to stop shopping altogether or go mine for your clothes.

To help with your vintage expedition — and to hone your eye so it can immediately tell the difference between a genuine grail and something that just looks old — I enlisted the aid of Ethan Wong, a fashion blogger whose writing is largely dedicated to explaining the history behind some of his favorite vintage pieces, and Mark Boutilier, a fashion influencer with an eye for secondhand gems. Here’s what they had to say…


T-shirts are probably what vintage stores are best known for. But according to Wong, camp collar and Western-style shirts in twill and chambray are great too, which he says are typically of higher quality than today’s fast-fashion alternatives. His favorite vintage shirts, however, are made of rayon — a fabric that he and many others are particularly obsessive about. “Good vintage rayon gabardine feels amazing,” he boasts. “Soft with a bit of heft and sponginess that helps it take a beating.”

As for Oxford button-downs, Wong suggests the old standby — Brooks Brothers. Besides, he explains, “They’re the most ubiquitous. It’s one of those things where people ask what brand they should look for, and Brooks Brothers is just usually readily available.” Keep in mind, though, you want to make sure they’re actually vintage. “After the 2000s, Brooks Brothers made their Oxfords slim fit and the collars shorter,” Wong tells me. “I look for ones that are 100 percent cotton and aren’t non-iron since I don’t like how stiff non-iron collars are. I want mine soft.” 

Speaking of famous brands, he also likes older L.L.Bean shirts, “because it’s not the current manufacturer” and the details are more refined. “I have an L.L.Bean sports vest with sleeves,” he says, an item that cost him less than 40 bucks. “It’s just so different from anything they currently put out.”  


Like with Oxfords, typically the easiest pants to find are World War II khaki chinos, which Wong likes since they’re wider-legged and higher-waisted than the modern J. Crew knockoffs. “[Vintage] khakis are everywhere because they made a bunch of them during World War II and Vietnam,” he explains. Less common are P43 pants in olive herringbone. Their defining feature — big, front-facing cargo pockets. “You might have to scour Etsy or eBay or get lucky at a flea market,” Wong says. They’re about $250, but again, you can’t compare them to the cheaper reproductions. “[Reproductions] just feel like they’re meant for reenactment,” Wong argues. “They’re still 100 percent cotton, but they just don’t feel great.”


Some of the most expensive and sought-after jeans — generally those from the 1940s to the early 1960s — originate from vintage shops. “They’re very rare, but I remember seeing a pair of 1960s jeans for $600,” Wong says. “If you find 1940s jeans, you’re looking at $500 bare minimum.” 

A cheaper alternative is a reproduction he can get behind — LVC, or Levi’s line of reproductions. “I have a pair of Levis 501 LVC from 1945,” he says. “They were made in 2001. I got them for $50.” He does recommend, though, to size up since the sizing used to be slightly different back in the day. They also didn’t have any buttons on the fly, so Wong had to have a tailor sew them on. 


As someone with a Sid Vicious-level attachment to my vintage Buco leather jacket, I can tell you straight-up, they don’t make leather jackets like they used to. For his part, Wong likes A-2 style ones, or what he calls “single-breasted zip.” “When you think of leather jackets and Indiana Jones, this is the style you’re thinking of,” he says. Not to mention, he adds, “It’s easiest to wear. You can wear them with button-downs and T-shirts. One of mine has a patch pocket and a Western-style pocket that’s angled downward like a suit pocket. It’s a small detail but it makes all the difference.”

Other vintage leather jackets he thinks fits the bill — double riders (“I prefer ones from the 1930s to 1950s, like Hercules or Buco, which usually have a cool label”); M43 military jackets (“Most field jackets are easy to find at vintage stores that specialize in old American clothing”); and  jungle jackets (“The pockets are really fun”). 

He does tend to avoid, however, any leather jacket with a hole, which he says is harder to patch up than other particularly worn second-hand items.


To Wong, the ties of yore are just more fun than the ones from today. “I have a blue foulard from the 1940s,” he tells me. “The squares are almost abstract; they’re not perfect squares. They’re more oblong and without perfect edges. I got it for less than $20. I’ve looked for stuff like it in other places like J. Crew, but they were unique to random department stores that had a dedicated tie designer.”


As far deal-hunting goes, Boutilier tells me antique shops are a great bang for your buck on jewelry. “I have a few pieces that I wear nearly everyday,” he tells me. “They’re simple sterling rings that flow very cohesively with one another. I purchased them from the same woman’s booth at an antique expo thing for around $20 each.” (For comparison’s sake, even a plain sterling silver ring with no character retails for at least $100; one thing to note, however — it’s important that there’s a .925 stamp on any vintage piece of jewelry, which indicates it’s sterling silver-ness.)

“In terms of styles, I look for more basic styles such as signets or ones with small stones,” he says. Stones on rings, Boutilier says, can also be a good indicator of value. “Personally, I’m a fan of turquoise and onyx,” he says. “While I’m certainly not a ring expert, if you’re finding sterling rings for under $50 at antique shops/resell shops, you’re doing something right!”