Mine is one from the 1989 Amnesty International tour. It is amazing how soft it has become over the years.
I still have my “All That Jazz. Senior Follies, 1980” t-shirt from my senior year in high school and a Barry Manilow Copacabana World Tour t-shirt from about '81.
Not that they fit.
A Dylan and the Dead tie-dye (go figure) from their '82 (?) tour.
A t-shirt from a local club that my hubby won singing karaoke back when we were dating in '93. “Norma Jean’s” is no longer there…
That’s not my oldest shirt, though. I have the blouse I wore on our first date, too!
1972 Boy Scout camp shirt. My G*d was I ever that thin?
My ex gave me a Rocky Horror Picture Show t-shirt, after much hunting around for one, back in 1982.
LIPS! (sorry, had to do it! 
)
I still have it, but never wear it. It’s buried in my dresser drawer. I sometimes take it out and admire it, but it’s strictly a keepsake now.
1973 WRUC T-Shirt. Don’t wear it much, though.
A tee shirt from 1977 with the robot from Queen’s album cover for “News of the World” on it. I also have one from their 1979 “Jazz” tour.
One of my oldest T-shirts was bought in the late-'80s. I don’t wear it any more because although the company still makes similar shirts, they sold the copyright to this particular design and the owner is not making them.
On the front is a circular design, mostly in yellow, tan, black and white. It depicts a B-17 bellied in in the desert. The skeleton pilot is hanging out of the window (I think he’s giving a “thumbs up”). A joshua tree (familiar to anyone who has been in the Antelope Valley portion of the Moave Desert) and a signpost that points to Lancaster and to Edwards AFB. A B-2 it silhouetted in the far packground. Around the top of the circle is “Mojave Desert” and around the bottom is “Aero Club”.
On the back is a bold yellow-and-black “X-West” logo.
A 1977 “Jedi in Training” Star Wars Tee-shirt (that’s obviously not a licensed product). I also have an “Empire Strikes Back” shirt from the Star Wars fan club from what…1979? 1980?
Fenris
A yellow t-shirt from the original production of “Emily and Her Friends”, a sappy kid’s musical about a babysitter and her charges. (I played piano in the ‘orchestra’ - me and a flute player.) I think this was from about 1977.
Wow my oldest t-shirt is from 1997. Guess I don’t really compare to anyone in this thread now do I? I don’t get to where it anymore since I got it autographed by one of my brothers fav. bands and gave it to him.
A t-shirt I got when the Red Army Orchestra and Choir came through Naval Training Center, San Diego back in 1989 when I was stationed there. They really were the Commie version, too!
Pretty cool keepsake. I don’t wear it cause then I’d have to wash it and I’m afraid it’ll fade.
I also have a Crater Lake t-shirt that I got in 1990 when I drove through the Park on my way home to Michigan. That get’s worn all the time - its one of my favorites. Held up pretty well too.
I think my oldest is a Bob Dylan/Tom Petty tour shirt from…geeze, when did they tour? 1985?
Still fits, but my wife won’t let me wear it in public. She claims it’s a tad “sheer” now. Bah. I call it “light and airy.”
My Pink Floyd tour shirt from 1987. If I ever have a 7-year-old, it will fit him perfectly.
I also have an old, Ocean Pacific T-shirt circa the mid-1980s. It’s riddled with holes, and I never wear it now. But I can’t bear to throw it away.
An ancient “Mother Love Bone” shirt from '88. There was a brief, glorious time when I could wear it and folks didn’t look at me oddly.
Chicago Cubs 1984 Eastern Division Champions. Because it’s one of the few red, white & blue shirts I have, I used to wear it every 4th of July. I also have my high school gym shirt (Bonnabel Bruins) from the '83-'84 school year.
T-shirt from 1992. A local Topeka artist drew a design of a hand coming down out of a cloud, throwing a lightning bolt at a man(mostly fried) holding a(mostly charred) picket sign. The words said “God doesn’t hate anyone, but he ain’t too fond of Fred!”
The “Voice for Choice” t-shirt I got my freshman year in college. It’s practically see-through at this point, I only wear it to clean in(it would be indecent to wear outside), but it’s ever so comfortable.
A 1982 AC/DC concert t-shirt.
First live show I ever saw, the For Those About To Rock tour
It’s in bad shape now…sheer and no sleeves but sometimes it’s just perfect.