Buying vintage means you save money and help keep clothing out of landfills, all while hunting for one-of-a-kind treasures, which can be thrilling and a little bit addictive. Plus, 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. I have a large collection of vintage men’s crewneck sweatshirts, denim jackets, and boxy novelty tees that I wear on a regular basis. I prefer to do most of my vintage menswear shopping in person, since it’s hard for me to know how men’s clothing might fit my body without trying it on, 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, 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 everyday for a year, many people are excited to experiment with fashion and bright colorful patterned shirts are an easy place to start. One of the coolest things about vintage clothing is you don’t have to spend a lot of money to experiment. You can find everything online 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.
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.