What is the oldest article of clothing that you still wear? I still wear a 40 year old bath robe.

I have a hoodie from my college days. That's about it, though. I recently donated most of my older clothes. 

I have a pair of Levi's 501 that I bought back in 1983 that I still wear.

Dad's dressing gown: he died 73 years ago. 

I have several pairs of these Circle Colored sunglasses I got in the 90's that I wear.  As for tops and pants, the oldest I have is 4 year old tank.

Hello Sailor:

I mentioned my Winston tee shirt..  I got that in 1989.  I have some suede Birkenstock's that are a little older.   My Birkenstock's are every day.  And, when the Winston shirt comes up in rotation, it gets worn.

excon

The oldest article of clothing that I wear (and then only rarely) is an old pair of work pants which I use as paint pants.... and I bought them in 2015.  Everything else has already hit the rag bag.  I wear out clothes quickly (even those paint pants are now on the "indecent" side).  Any old clothes that I didn't wear out I donate (I seem to have a habit of washing them in too hot of water and they shrink).  

I still have a Harris tweed jacket that I bought in 1988, but I can't wear it anymore. I didn't have the "dad bod" back then.