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The Best Vintage T-Shirts for Men

“They don’t make ‘em like they used to” is a common refrain, but when it comes to T-shirts, there’s some truth to it. The vintage market — especially vintage tees — is full of high-quality shirts that, more often than not, are way cooler than anything you’d find on a shelf nowadays. Vintages are full of life, just waiting to be rediscovered by a new audience. Plus, they’re a great way to show off personal tastes or interests.

Hunting for vintage tees? Well, that’s a different story. As cool as vintage shirts are, the market for them is incredibly robust, not to mention overwhelming for beginners. Diving into the resale rabbit hole can make your eyes bleed pretty quickly, as they’re filled with hundreds of listings where it’s tough to figure out whether or not what’s listed is even legit. 

Don’t fret: At SPY, we spoke with some experts about the best kinds of vintage tees to shop, as well as where to find them. Because listings of vintage tees come and go so quickly, we’ve linked out to some searches to make things easier for you to find as well as some modern options to give you a general idea of what to look for. We even got some intel about what to look for when doing some online browsing for the perfect tee of yesteryear. 

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The Best Vintage T-Shirts: At a Glance

BEST OVERALL

The Band Tee

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MOST FUN GRAPHICS

The Harley Davidson Tee

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BEST FOR LIVED-IN FEEL

The Mechanic or Car Tee

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ALSO CONSIDER

The Collegiate Tee

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UNEXPECTED SURPRISE

The Camp Tee

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Best WARDROBE BASIC

The Blank Tee

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BEST CLASSIC

The Recognizable Graphic

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BEST SURPRISE

The Pop Culture Reference

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ALWAYS A HIT

The Sports Tee

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What the Experts Say

To help source this piece, SPY spoke with Daniel Brown, the founder and owner of vintage shop Nylo Wool in Dallas, Texas, and digital creator/fashion TikTokker Xander Torres. When asked about what makes a good vintage tee, Brown states, “When I’m looking for tees for my shop, my first priority is age. I tend to go for older, 80s being the newest, and then focus on the style of the tee. I gravitate towards old gym tees, humor tees, and stripes. When determining the age, the best luck you’ll have is doing some label research.”

BEST OVERALL

$34.50

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“Concert/band tees, like this Van Halen World Tour tee, are still going strong in the vintage community,” says Brown. Old bands — especially ones that are considered to be legends — are pretty timeless, doubly so if they’re known for their slick graphics. 

They’re also a great way to show off personal taste in both style and music. And, more often than not, they’re just really cool. Torres also pulled a sick Joni Mitchell shirt with a graphic: “There’s a subtlety to it that is refreshing,” he says. “It’s a great design. It’s perfectly faded. Plus, I mean, it’s Joni fucking Mitchell!”

There are a handful of different routes to go with vintage music tees, too, from opting for something louder or playing it down. Just maybe stick to beloved icons. “Stick to the classics when it comes to bands, and you won’t be embarrassed you have it ten years later,” Brown adds.

MOST FUN GRAPHICS

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Why It Stands Out: Typically adorned with sweet graphics, vintage Harley Davidson tees are an easy way to add some attitude to an outfit. It’s the right amount of swagger without needing to worry about whether or not you’ve got a motorcycle to match.

Made For: Those who want to pretend that they ride a motorcycle. 

ROI: A particular one that Brown selected was a 60s-70s tee, notable because “you don’t see them as often as the 80s-90s Harley Tees, which makes them cooler and more valuable.”

BEST FOR LIVED-IN FEEL

Why It Stands Out: “Any mechanic shop or car tee is killer, in my opinion, especially this one from the 1950s,” says Brown. “The wear and tear on mechanic tees give the tee a lived/worked-in look and feel. Can’t beat that real wear-and-tear feel.”

Made For: Those who want their vintage tees to feel, well, vintage. Part of the appeal of getting vintage gear is feeling like it’s had a whole other life before it arrives with you, and that’s the case here.

Hot Take: Getting distressed or worn tees is much better than buying any sort of pre-distressed option online. 

ALSO CONSIDER

Why It Stands Out:  Old collegiate or fraternity tees typically look like they just came out of the wardrobe for Everybody Wants Some!! (a movie you didn’t likely see but one that has incredible sports style). That’s a good thing.

Made For: “Didn’t make it into a fraternity in college? Well, you can still look like a frat bro by finding a vintage fraternity tee,” says Brown. 

ROI: “I love the whole fraternity/varsity look, and the fabric these older tees come in is perfection,” he adds. “Just make sure you brush up on your Greek lettering before you go out wearing it.”

UNEXPECTED SURPRISE

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Why It Stands Out: “Souvenir/camp tees give me Wes Anderson vibes,” says Brown. He found one that’s from a Lutheran camping trip and states that he loves it “because it’s striped and a ringer. I wasn’t raised Lutheran, but that wouldn’t stop me from sporting this one often.”

Made For: Camp Staff tees often evoke the outdoors and already have a vintage appeal to them, so finding one is like a double dose of nostalgia. 

ROI: Without a doubt, a camp tee will be a great conversation starter — the more esoteric, the better.

Best WARDROBE BASIC

$45.00

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Why It Stands Out: “What’s not to love about the classic white Hanes blank tee,” says Brown. He’s right. (Remember how The Bear sent the popularity of a well-fitting white tee into the stratosphere?)

Made For: Those who want to look classically cool and effortless. “Don’t sleep on the Americana style of classic white tee, Levi’s 501s, and a beat up motorcycle jacket.”

Hot Take: The white tee may feel basic, but it’s far from boring when styled smartly.

BEST CLASSIC

Why It Stands Out: “This is just a killer tee shirt,” says Torres. “A great, easily recognizable design that is a little bit edgy and a little bit sensitive. It has the sex appeal of a vintage band tee while at the same time hinting at artistic sensibilities.”

Made For: “This is, in my opinion, the perfect vintage tee,” he adds. “It would work in just about anyone’s wardrobe, isn’t too terribly expensive, and it just looks damn cool.”

Hot Take: Don’t be afraid to go really esoteric with your vintage tees to evoke a real if you know, you know vibe. The people who get the reference will more than likely love to strike up a conversation with you about your tee!

BEST SURPRISE

$40.00

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Why It Stands Out: In a nod to his IG handle, Torres picked out a really sick X-Men tee as a great example of a good pop culture reference. “In all my years of buying vintage tee shirts, X-Men shirts have remained a high-ticket item in the resale market,” he says. “Besides being very, very cool, these shirts are also pretty rare, so getting one in good condition is a flex in and of itself. The designs on these are almost always top-tier.”

Made For: “Fans of comic books, movies, superheroes, and pop culture who want to flex their nerdy side without having to wear ugly graphic tees,” he adds.

ROI: A cool way to show off your own cultural bonafides and get a fit off at the same time

ALWAYS A HIT

Why It Stands Out: Torres specifically pulled this Olympic tee for the story behind it. “In 1992, the Lithuanian Olympic basketball team was incredibly talented but also ridiculously broke,” he says. “Fortunately, the Grateful Dead (yes, the iconic hippie jam-band) stepped in and sponsored the team. They even provided these insanely cool tie-dye Lithuania basketball tee shirts. These shirts are a badass and a particularly drippy piece of sports history.” That story speaks to why sports tees stand out amongst the vintage tee market. It’s always fun to hunt down a team shirt from a year where they were particularly popular, unique, or cool. 

Made For: Those who love the home team. Duh. But they can also be for those who want to tell a cool story while out and about. 

Hot Take: Sometimes, a tee can hit a variety of different interests. “This tee is cool with sports fans, history buffs, music lovers, hippies, potheads, people from Oregon, and people who don’t mind dropping 300 bones on a tee shirt,” says Torres.


William Goodman

Contributor

Will Goodman's work can be found at Complex, GQ, and InsideHook. He is based in Washington, D.C.

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