I have a pair that's from my high school days. I'm 47 years old, so that makes the underwear about 30 years old. Can anyone top that? The underwear is boys' size 20, but they still fit. They're a little threadbare, but that's an advantage on a hot summer day. I think I can get at least a few more years out of them. (Obviously, I don't wear this pair every day. I wear them mostly for dirty outside jobs.) I'm a lifelong bachelor, so I don't have a wife to throw away my stuff that's old but still good....