I also tend to hang on to stuff irrationally.
I have one suit with damaged pants that I still can't bear to part with.
Shirts are usually pretty frayed by the time they get trashed.
Pants always wear in the crotch first (see above), and get patched at least once and continue being used.
For shoes, I have only recently gotten into higher quality shoes, and haven't gotten to the recrafting point yet.
I'm curious to hear others' points of view.