Well, shirts seem to slowly evaporate. The material becomes thinner and thinner, until you can't take it off without the delicate gossamer tearing. At that point I have to throw it away.
Trousers and boxer shorts fail in the crotch. I don't know why - I don't think I put an especially high load on that area. But it gets to the point that when sitting on the train, I have to keep my legs carefully closed or else the lady across from me will get an ugly eyeful.
You used in the glorious 70s to be able to get nylon underwear here. Now that lasted!
I have essentially three levels of clothes. Work and church: underpants, long-sleeved shirt, trousers (cheap, always the same), tie (thrift store), socks, shoes (also always the same, cheap jogger type). Other formal occasions outside: underpants, short-sleeved shirt from thrift store, jeans (cheap), flip-flops (we call them thongs here, but that could lead to misinterpretation). Inside or out walking the dog, replace the underwear and jeans with a pair of shorts (always the same).