I think I would, especially the basics (black simple, etc) when I felt like it was time to go ahead and buy a new pair. In the end, they are shoes and if it would help another woman feel better about herself in a job interview (Dress for Success) then I would be happy to donate them. I generally go through all of my clothes once a season and get rid of the things I haven't worn in a while and that includes me shoes. Of course, there are some that I do have a sentimental attachement too and probably couldn't let loose of!