I've 'thinned the herd' a few times, reducing my inventory by a few dresses or shoes I rarely wore, but only one time did I truly purge. That was the day after my wife of (at the time) 17 yrs discovered my stash and was dumbstruck/angry/upset/ etc. I showed her that she came first in my life and threw away everything but my pantyhose. The pantyhose were part of our compromise...she could handle me wearing pantyhose, but she couldn't handle me dressing completely. I was actually OK with that situation for a few years, then the urge came back. I started acquiring a dress here, a skirt here, and now have a small wardrobe that she doesn't know about. I feel terrible dressing behind her back again, but she just can't understand why I that ingrained desire won't go away. But that's a whole 'nother discussion!
My biggest regret from that purge? a lovely pair of leather pumps that fit size 11's like a glove. I've never been able to find another pair that were so comfortable since!