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.