5 Vintage T-shirts That Cost Two Arms and a Leg

by John Amato

What’s the price of a memory? We’d argue that it’s priceless!

As you chase down, bid on, or replicate your vintage t-shirt of choice, you’re attempting to put a price tag on an emotion, a memory, an inimitable moment in time.

It’s your first concert, or what you spent your first paycheck on, or the first time you fell in love.

“I'd trade all my tomorrows for one single yesterday.”
- Kris Kristofferson

That said, priceless vintage t-shirts go beyond age and nostalgia. They comprise a delicate mix of high-quality fabrics, limited availability, high-caliber craftsmanship and artistry, and, of course, the notoriety of the subject.

Jupmode might be a few years shy of Keith Haring’s notoriety, but we’re definitely getting everything else right in our vintage t-shirts.

We’re therefore qualified to give you this rundown of notable vintage t-shirts as we drop some gems about:

  • What to look out for when choosing a vintage t-shirt
  • Why some vintage t-shirts cost two arms and a leg
  • How you can replicate the vintage aesthetic on a t-shirt

Let’s break down this list of vintage t-shirts that sold at eye-watering prices. Keep in mind that when we talk about vintage, we’re looking at least two decades old as well as the retro aesthetic.

1 - The Nike and The Beatles Revolution Collaboration, 1987

The Beatles and Nike collaboration vintage t-shirt

Photo credit: Ragstock

We’ll put you out of your misery and start with the highest ticket vintage t-shirt on this list.

This deceptively unremarkable gray t-shirt depicting the Beatles as actual beetles with Nike scrawled on the drum is a rare vintage t-shirt going for a whopping $50,000 or best offer on eBay.

Why It’s Expensive

In a nutshell, it’s a vintage t-shirt based on The Beatles, one of the greatest bands of all time. It’s also linked to sportswear giant Nike and has limited availability.

We’ll keep it brief, but here’s the tea.

In 1987, Nike licensed the Beatles’ song, “Revolution”, for its first major television advert. It was immediately controversial since the band didn’t want their song used but had no rights to it.

Eventually, Nike pulled the plug on the Revolution campaign and discontinued the merchandise, making the t-shirts already produced rare and valuable.

Why We Love It

This tee meets our requirements for a vintage t-shirt:

  • Soft feel: The tee looks so soft that it’s begging to be worn.
  • Quirky artwork and warm color palette: Vintage t-shirts tend to be screen printed in warm tones or distressed designs which soften the look and ramp up the nostalgic factor.

Pro Tip: If you wish to replicate a vintage t-shirt feel, go for a tri-blend t-shirt. Tri-blend shirts combine cotton, polyester, and rayon in varying ratios to give you the softest worn-in t-shirt.

Jupmode’s Michigan is Super shirt perfectly pairs these vintage t-shirt qualities with its super-soft tri-blend material and nostalgic print in bright, warm tones.

soft tri-blend vintage t-shirt from Jupmode

"As a former Michigander, Superman ice cream is still one of my favorite summer traditions! I was so excited when I saw this shirt! It’s super soft and true to size!"
- Emily P., United States

2 - Grateful Dead T-shirt, 1967

The Grateful Dead yellow vintage t-shirt

Photo Credit: Sotheby’s

For Deadheads, any original piece from the Grateful Dead is priceless. This 1967 original yellow vintage t-shirt with bold Grateful Dead typography sold through Sotheby’s for $17,640—adding up to $19,315.80 with taxes and buyers premium.

Why It’s Expensive

The Dead t-shirt has many claims to fame that justify the hefty price tag. It is:

  • 50 years old and in mint condition
  • One of the original t-shirt designs the band released
  • Connected to the inner circle of the Dead, having belonged to Dan Healy, the band’s audio engineer
  • A limited release as only 150 t-shirts had the design
  • Part of the legacy of Allan Gut Terk, a former Hell’s Angel, artist, and key contributor to the 1960s counterculture scene in California

Why We Love It

Nothing beats warm mustard yellow as a background palette for your vintage shirt. It serves up a heavy dose of nostalgia.

This warm yellow pops up in Jupmode’s selection of vintage t-shirts as well as in the colors we choose for our t-shirt prints. Here are a few examples in the table below.

Jupmode Mustard Yellow Vintage T-shirt Selection

midwest goodbye shirt

Midwestern Goodbye Shirt

mustard yellow t-shirt with a pet slogan

Ask Me About My Dog Shirt

mustard yellow t-shirt celebrating University of Toledo

UToledo Love Cropped Shirt

We also love the simple yet bold typography on the Grateful Dead t-shirt. It commands your attention and is memorable while still fitting the vintage aesthetic.

This simple yet eye-catching design feature is one we reach for time and again with our vintage shirt designs.

Below are three great examples of bold vintage-style typography on t-shirts.

Jupmode Bold Typography Vintage T-shirts

black t-shirt with four one nine slogan

Fancy Four One Nine Shirt

brown t-shirt with bold typography print

Happy to be a Falcon Shirt

blue t-shirt with you belong slogan

You Belong Shirt

3 - The Beatles Butcher Cover Promo T-shirt, 1966

The Beatles butcher cover promotional vintage t-shirt

Photo Credit: Defunkd

Baby doll parts and raw meat seem counterintuitive as promotional images for an album. Yet, the controversy surrounding the shocking images makes this t-shirt valuable, selling at auction for $20,000.

Why It’s Expensive

The image of The Beatles dressed as butchers amidst doll parts and raw meat was disturbing and controversial.

The uproar from fans forced the record label to cancel production of the promotional merch for the English rock band’s ninth album, Yesterday and Today.

Somehow this piece survived the culling. The shock factor of the artwork, coupled with its rarity, makes it extremely valuable.

Why We Love It

The creativity of a t-shirt print can make or break the tee’s success. We love that they took a wild chance on the shocking visuals.

Pro Tip: You don’t have to go the gory way to elicit a reaction from the artwork on your vintage shirt. Humorous slogans and puns or heartfelt messages can be just as memorable.

Take, for example, this slogan vintage t-shirt we made custom that plays on the words, “piece of me” with “pizza me”.

funny slogan vintage t-shirt

 4 - Andy Warhol Keith Haring T-shirt, 1986

vintage t-shirt with Keith Haring portrait by Andy Warhol

Photo Credit: Artsy

What’s not to love about artists creating art about other artists?

Andy Warhol’s portrait of famous street artist Keith Haring on a basic white t-shirt sold for $11,866.

Why It’s Expensive

There are several reasons this t-shirt is worth over $11,000:

  • It’s an Andy Warhol drawing, an art icon whose works have sold for over $100 million at auction.
  • The subject is a famous street artist, Keith Haring, known for his energetic, cave-dweller-style art.
  • Neither of the artists are alive today, which exponentially increases the value of their pieces.

Why We Love It

There’s a reason white t-shirts continue to be a staple, year in, year out. They are a forgiving canvas that allows the artwork or message on your t-shirt to shine.

Here are some of our favorite vintage-style t-shirts from Jupmode. 

Jupmode White Vintage Style T-shirt Designs

white t-shirt with vintage downtown Toledo print

Better in Toledo Vintage Downtown Shirt

white t-shirt with a slogan about Toledo

Doin' Better in Toledo Shirt

white Jupmode t-shirt printed love is love

Love is Love Shirt

5 - Run DMC vs. Adidas T-shirt, 1980s

vintage Run-DMC and Adidas t-shirt

Photo Credit: Defunkd

Last, but certainly not least, is the Adidas and Run-DMC collaboration that followed the release of the rap group’s 1986 hit record, “My Adidas”.

Following the success of this cultural moment, Adidas gave Run-DMC a million-dollar endorsement deal—the first such deal on the hip-hop scene.

While the Run-DMC and Adidas clothing range is still available, the original vintage t-shirt from the 80s is a collector’s item that fetched $13,000 in its last sale.

Why It’s Expensive

Two reasons make this Run-DMC vintage t-shirt valuable:

  • Hip-hop tees have always been scarce, and gaining an original piece from an influential hip-hop group's glory days and concerts make it doubly valuable.
  • This shirt came from a groundbreaking partnership between one of the biggest rap groups of the time and a sportswear company.

Why We Love It

We hope you’ve caught onto the fact that we love all things Midwestern. It’s no surprise that we love seeing art that celebrates iconic cultural moments from other cities.

The Run-DMC and Adidas collaboration was the first of its kind and inspired so many artists, fashion brands, and an entire generation of vintage t-shirt buffs.

Check out some of the culture-defining, historical people and places we celebrate with these Jupmode vintage t-shirts.

Jupmode Vintage T-shirts Celebrating Midwestern Cities

gray vintage t-shirt celebrating Moses Walker

Moses Fleetwood Walker Shirt

Rusty’s Jazz Cafe vintage t-shirt

Rusty's Jazz Cafe Shirt

gray vintage t-shirt with Macmen print

Macmen Shirt

"This shirt is very soft and comfortable and true to size, which is consistent across all Jupmode shirts I own. I love Toledo. It’s my home and where I grew up, and wearing shirts like these that create conversations allow me to share my passion for my home with people that don’t know much about Toledo."
- Michael, United States

Jupmode vintage t-shirts photo snippet

Express Yourself With Your Vintage T-shirt

Vintage t-shirts pay homage to historical moments and cultural items. They also enable us to relive the best of the past.

That said, if you don’t want to drop a bundle on a t-shirt, consider recreating the vintage aesthetic with Jupmode.

Alternatively, shop our quirky, funny, and nostalgic collection of vintage t-shirts inspired by the Midwest and overall good vibes.

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  • Comment Author: Nick

    I really enjoyed this article…learned a lot. Thank you so very much and please keep up all your great work at Jupmode…your efforts are very much appreciated

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