In this section I highlight the worst vintage t-shirts ever created. No, I don’t mean Bad in the 1980s Michael Jackson way … I mean: offensive, vile, in poor taste, politically incorrect, or just plain ugly.

T-Shirt: Marky Mark and the Funky Bunch

Type: Band

Offense: Warning, contains nudity and sexuality, viewer discretion is advised.

Uses: Wear it, I dare you. It takes reverse cool in to unchartered territories.

I totally respect Marky’s acting career but this t-shirt causes audiences more pain than Max Payne. What is he doing with his hands, giving himself an Italian Job? Even Dirk Diggler wouldn’t have the balls to release such filth.

Aside from this shirt being a MM&FB band tee, it’s wrong on multiple levels. For one, it’s an ugly 1990s all over print (which are kinda due for a comeback). The best/worst part is that Wahlberg is shirtless and making a lewd gesture, conveniently located on your chest.

For the first time in this section I actually highly suggest this t-shirt. If you get a kick out of the super lame, enjoy turning heads and offending people, this shirt is right up your alley. It trumps every t-shirt on our list of the “10 Worst Vintage Band T-Shirts You Must Wear”.

Check out the previous worst entry: vintage devo t-shirt.

After visiting numerous skateboard forums to research this post I quickly learn how massive the scope of vintage skate tees really is. Out of fear of being called a poser (flashbacks to my lame skating days in the ’80s) I enlisted the help of a godsent who has one of the largest collections of vintage skateboard tees in the world. His name is Thomas and he occasionally musters up the strength to sell one from his collection via his eBay account rubysoho08.

Without further ado we present part one in a three part series. 

21. vintage Thrasher David Hackett t-shirt
22. vintage Santa Cruz Jeff Grosso Toybox t-shirt
23. vintage Powell Peralta Kevin Harris t-shirt
24. vintage Santa Cruz Rob Roskopp eye t-shirt
25. vintage Powell Peralta Animal Chin t-shirt
26. vintage Powell Peralta Tony Hawk t-shirt
27. vintage Santa Monica Airlines Boxer Kid t-shirt
28. vintage Powell Peralta banner dragon t-shirt
29. vintage Santa Cruz Tom Knox t-shirt
30. vintage Powell Peralta Bones Brigade t-shirt

Check out part 2 to the top 30 vintage skateboard t-shirts.

If you’re looking to snap up one of these badboys, good luck, you’d have better chance landing a 900. Keep your eyes peeled to this search for vintage skateboard shirts on eBay or use one of the brand specific links above to refine your search. 

Here’s a gem from 1943 that was recently sold by vintage clothing merchant torray. It was acquired from the widow of a WWII veteran who resided in the bay area of California. The art was hand drawn by a friend of her husband’s who made it to celebrate deployment.

Home made t-shirts were quite common back then, the t-shirt was quickly becoming a new medium for messages and people were percolating with social commentary (and couldn’t wait 60 years to wait until Threadless was born).

Get a load of the 1940s Hanes logo which almost inspired the title of this post to be “Mickey Gets His Hanes on Hitler”. It just didn’t have the same attention grabbing properties, know what I mean?

Happy belated birthday Adolf, we hope you enjoyed your gifts!

This t-shirt celebrates Mickey during his prime, in fine form and battling evil. It’s hard to believe only a few decades later the poor little rodent falls on hard times. Sorry Walt, there’s more unauthorized vintage mickey mouse t-shirts.

My Vintage T-Shirt is a section written by our readers. Thanks to Ron Graff over at craftymodolls for sharing this shirt and great story. If you have a rare vintage t-shirt and a great story please contact us.

When ‘Easy Rider’, the movie, came out in 1969 I was 19 years old and living in London while studying at the famed Morris School of Hairdressing. The school was situated in the heart of Soho, directly opposite Paul Raymond’s Revue Bar. What a location! One could look out of the upper floor school windows and see directly into the Revue Bar dancers’ changing room windows across the road!

Those were the heady days of Soho – all sex shops, strip joints, clubs, studios and fashion boutiques. Carnaby Street was just a five minute walk from the school. If you’ve ever seen any of those old movie clips of ’swinging’ London in the 60s, you get the idea!

I bought the shirt that year, shortly before leaving London to continue my misspent youth as a newly qualified ladies hairdresser. It wasn’t ’till about a year later that I saw the film. Moved to tears, I thought then as I think now, that it is an outstanding commentary about many things – not just the obvious search for the American Dream. Relevant then, and perhaps even more so today.

Maybe there was always a bit of Captain America hidden inside me – it just took an amazing movie to open the door.

The same year that I saw the film, 1970, I was working on the Isle of Wight. It was also the year of the last IOW Festival. Outdoing by far the massive crowds of the 1968 and 1969 events, 600,000 hippies and freaks invaded the island to see Jimi Hendrix, The Doors, The Who, Joan Baez, Ten Years After, Leonard Cohen, Hawkwind, and all the magnificent rest.

I was there and so was this rare t-shirt!

• View the vintage Harvey Milk t-shirt previously featured in My Vintage T-Shirt.
• Search eBay for a vintage Easy Rider T-Shirt.

An ongoing project to document all of the exquisite vintage Harley Davidson clothing. 

Item #2: Harley Davidson Keep America Beautiful T-Shirt

Availability: Explore Vintage Harley Shirts on eBay 

Dealer Customization: Blocker’s in Parryville, PA

Decade: 1980s

Label: Worn

Harley Fact: The Harley Davidson company and riders aren’t very fond of Japanese motorcycles.   

Approximate value: $100-$200

Check out previous vintage harley davidson shirts and clothing. 

Every so often we feature an interesting vintage tee that’s currently on the eBay auction block. Please feel free to link us if you create or discover an auction we might like.

Description: vintage 1970s Fila Bjorn Borg tennis shirt

Sold by: houseofcult

Measurements: 20″ pit-to-pit by 26″ length

What the Seller Says: You are bidding on a beautiful and original MEGA RARE TENNIS POLO FROM FILA, THIS KIND OF POLO WAS WORN BY BORG IN HIS EARLY DAYS!! REALY A COLLECTIBLE SHIRT!

What I Say: To complete the outfit you’ll just need the shorty Fila shorts, the matching striped headband and wristbands, the BJ logo socks and the Diadora Borg Elite Trainers.

Check out our post on the top 5 vintage tennis shirts.