I'm on team "no, not really" -- I purge fairly frequently but I don't give away things I really love, I just store them on the top shelf of my closet for use later (though now I have a whole size 4 to 6 wardrobe stored on that top shelf and in my regular closet too). If I later decide to get rid of it, then I've had plenty of time to think about it. I do miss some things, but I never gave them away, I wore them out to the point that I threw them out.
My mom had great clothes in the 60s, that she stored in the basement, and when I was a teenager (in the 80s), I would go through every once in awhile and pull out a piece. She probably didn't know I was doing that and one day gave everything away to charity. Some of the stuff I wasn't gutsy enough to wear as a teenager but I totally would have worn it in my 20s (in the 90s) b/c then I had a more retro-inspired style. That is the only regret either one of us has of giving things away. From that I've learned to hang onto dear pieces for myself or for future generations.