What are the oldest pieces of clothing you own?

I knew a girl in high school who worked at the T-Shirt World shop in the mall in 1986-87.
We had worked together at the ice cream parlor in the same mall, but we got fired for smoking pot in the back of the shop.

Anyway, she made me several shirts, and I still have one.
A green polo for a fictional bar she made up called O'Flaherty's.

 

Some old ties from at least 25 years ago.

 

I have a black T-shirt from the Onion that reads, "Your favorite band sucks," and it's more than 20 years old. I intend to be buried in it.

 

I have some very old ties.

 

Well, I've got a couple ties of my grandfathers' that have to be from the 1930s, a couple dozen of my dad's, and even 10 or so of my own. I wear ties about twice a year, so I'm pretty well set.

 

I've got some old ties; oldest one I really still wear is the tuxedo I was married in 20 years + ago; still fits and I've gotten a great deal of use out of it since I wear it at least once or twice a year.

 

Have a Jacksonville Jaguars shirt from before they played, when the Jaguar looked too much like the car logo for the car company's liking. It was changed.

 

One of the more awesome things I've seen is a guy's wife who made a quilt for his man-cave couch out of his old T-shirts. That is love personified, right there.

 

I have a couple of t-shirts from the mid-1990s, including a Grateful Dead inspired Lithuanian basketball shirt which I got at the Atlanta Olympics.

I still have the shirt which I wore on my first date with Mrs. W in 1997. I break it out every now and then.

I had 3 suits made in 2000 which now fit again and I wear them from time, as does my wedding tux from 2001.

 

I used to have a t-shirt compulsion. I had way too many. They took up my entire dresser, and there were still a lot of them that didn't fit in the dresser.
I had no room in any of my closets or drawers for anything by t-shirts.

I wanted to have them sewn into some kind of wall hanging or blanket.
The wife looked at me as if I were insane.

I took almost all of them to Goodwill.
I am down to only three drawers of t-shirts now, and likely to pare down again in the near future.

 

I still have a V-neck sweater for my high school that I got when I was a sophomore in 1970, my old letter jacket (Class of '73) and a leather fringe jacket that I bought in the summer of 1972 when my family took a sidetrip to Matamoros while we were vacationing at Padre Island.

I also have, somewhere in my possession, a pale blue dressing gown allegedly from when my father was a baby, which would have been around 1931-32.