Buying vintage clothing will save you money and help rescue perfectly good clothing from ending up in a landfill, all while taking you on a thrilling and somewhat addictive hunt for one-of-a-kind treasures. Since fashion trends are generally cyclical and inspired by the past, you can usually find near-identical versions of what is being sold by high-end fashion brands for a fraction of the price on eBay, Etsy, or Poshmark. What I really like about vintage menswear is sharing it with my fiancé. Over the last decade, I have accumulated a large collection of vintage men’s crewneck sweatshirts, denim jackets, and boxy novelty tees that I wear on a regular basis. I do most of my vintage menswear shopping in person, partly because I love the thrill of finding a gem at the bottom of a bin in a suburban Goodwill, but also because it’s hard for me to know how men’s clothing might fit my body without trying it on. But there is value to shopping for vintage clothing online. For one, you can search for highly specific pieces, and things are often laundered before they are sold. But even if you’re a men’s sample size, it can still be overwhelming to sift through thousands of vintage chinos or perfectly worn-in button-downs on eBay. So to help you (and me) find the best vintage menswear online without drowning in options, I asked Brian M. Davis, owner and founder of vintage menswear store Wooden Sleepers, for the tips and tricks you need to find the best vintage menswear online — including fun patterned shirts for spring and summer, stylishly baggy chinos, and not-too-expensive denim chore jackets.
If you’re hoping to score something you can wear right away, before tailoring (and after washing it of course), you’ll need to put a little work in up front. Vintage sizing is notoriously unreliable, so most collectors only pay attention to each garment’s actual measurements. “I just can’t emphasize enough how helpful it is to compare the measurements of something you own that fits you well with the measurements that are being provided by a seller,” Davis says. Take your best-fitting shirt, jacket, or sweatshirt, lay it down flat on a table, and measure the chest, length, and sleeve. Keep these measurements handy to compare with how people are measuring things online. If a seller doesn’t list measurements, don’t be afraid to ask for them. “A great thing to ask would be ‘What’s the pit-to-pit measurement on this shirt?’ If it’s 20 inches and the one from your closet is 24, then you know that shirt is going to be too small,” says Davis. Pants are also measured flat across the top of the waistband as opposed to all the way around. So you could measure your own pants that way, or if you know you have a 32-inch waist, you’ll want to look for a number that’s around half of that.
Davis says because feedback and reviews on resale sites are so dominant, people are generally upfront about any damages or stains and don’t want to misrepresent anything. Finally he recommends not buying things that will just become a project to fix. “I have to look at something and be like, Is this more trouble than it’s worth? Some spots or whatever can add to the character of an item, but a busted zipper is just going to be a headache and end up costing you a bunch of money.” With that in mind, here’s his advice for finding great vintage clothing in different categories.
Colorful Summer Shirts
After wearing a version of the same outfit every day throughout lockdown, many people are excited to express themselves again and bright colorful patterned shirts are an easy place to start. One of the coolest things about vintage clothing is you can experiment without spending much money at all. Secondhand resellers are packed with everything from classic Hawaiian shirts (Davis recommends vintage Reyn Spooner) to brightly colored seersucker, and tons of quirky novelty prints to match any warm-weather hobby you can think of. “It’s endless. That’s one thing that can be maddening about looking for this stuff online, but also sort of fun,” he says. Try plugging in some specific summer-weight fabrics into your search — like vintage seersucker, madras, or batik — and look for patterns like vintage paisley or vintage patchwork.
As a general rule, Davis recommends searching for classic American menswear brands because there is usually a lot available and the stuff even from the ’80s is made of high-quality materials. This vintage color-blocked Brooks Brothers seersucker shirt may not be super-rare, but it is a very good deal.
These two vintage Polo Ralph Lauren Hawaiian shirts are also great options for anyone looking to show off a little this summer.
Davis says you can find nearly any pattern imaginable. “I really like fabrics that have certain specific seasonal motifs, like vintage men’s sailing print shirts.” Some are more absurd than others, and he says the key to making them look cool is all about how you mix it up. Because they are historically preppy in nature you’ll want to avoid wearing them with other traditionally preppy things like a pair of khakis with lobsters embroidered on them for example. Instead go for something more subdued like jeans.“You kind of want to mash these things up so that it’s not so one dimensional,” he says.
Shirt Jackets
Lightweight jackets are important layering tools that can turn a simple white T-shirt and jeans into a fully formed outfit. But as we have seen with the shacket trend of the past few years, an unbuttoned shirt made of slightly thick or rigid cotton can do the same job. “A kind of hack that I’ve always done is to wear military shirts as lightweight jackets because actual military jackets are kind of too heavy for spring, but military shirts, just by the nature of the fabric, are pretty hefty and substantial,” Davis says, stressing that you want to look for all cotton rather than the synthetic blends that were introduced in the ’80s because the all-cotton shirts are a lot softer. “If you search for OG-107 military shirts (or pants) you’re going to find the good stuff in my opinion,” he says. This one has two chest pockets big enough for keys and a wallet.
Denim Jackets
If you want an actual jacket instead, there isn’t much that’s cooler, or more widely available, than a vintage denim one. Because there are so many, Davis recommends using filters to refine your search. He suggests searching in the actual vintage sub category on eBay as opposed to the clothing, shoes, and accessories category, and he says you’ll have better luck finding the best stuff if you get rid of things that look professionally photographed. Searching for a specific brand can really help narrow things down, too. Levi’s is an obvious one, as well as Wrangler and Lee, but according to Davis “virtually every clothing brand ever has done a take on the denim jacket.” So you might find something unexpected by searching for things like Osh Kosh B’gosh (trust us) or Tommy Hilfiger. This Wrangler trucker jacket has a western feel giving it a more unique look than a classic Levi’s trucker.
Denim chore jackets with their boxier fit, big patch pockets, and corduroy collars look good on literally everyone. They fall into one of two categories: lined or unlined. For warmer weather, you’ll obviously want to find one without the blanket lining. Other than that, just find one that you think looks cool. “A lot of these things can get really expensive and really intimidating, depending on how old and rare they are,” says Davis. If you’re not a serious collector, there is no reason to spend $500 dollars on a vintage 1940s workwear piece. According to him. you can get great ’80s and ’90s versions from brands like Carhartt that have all the wear patterns and the same basic silhouette without the hefty price tag.
Roomy Pants
“Having my store has made it clear to me that guys want fuller-cut pants with a higher rise, and they are willing to pay for it,” Davis says. Men’s pants have slowly but surely been getting wider and roomier — but not at a mass level, so buying them new is still pretty expensive. “If you search for vintage Polo, Lands End, or Eddie Bauer khakis, you could probably get a pair for around $15 with a high rise, a single pleat leg, and a nice nine-inch leg opening at the bottom. That’s going to give you that full breezy kind of look that you want right now at a super-low price point,” he says.
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