Christin......This is way too funny for me to answer......I have the dreaded Family curse of KEEPING things...handed down from one weird generation to the next, the curse AND the things!
I am relieved that you have limited the answer to "things we still wear." Please do not spread this around, but I literally have entire outfits, lovingly packed away in preservation, due to "sentimental reasons," (like the outfit I wore on my first date with my husband, 46 years ago) Is that old and creepy enough for you? Of course I don't wear it. It ceased to fit me 40 years ago! LOL
I do have a 50 year old jacket that I still wear occasionally. At the Post Office one day, a guy I grew up with, walked up to me and tugged on the sleeve.....and said, "Paula, really, if it's about the money, I can lend it to you."......Is that funny or what? I laughed so hard. I was actually AMAZED at his memory!
I can't get started on this subject....too much self-disclosure! I'll get quarantined to a padded room! LOL Great question!