It's so interesting to read all these replies. I've been reading some minimalist blogs lately that really encourage purging but it's good to see both sides of the story; both the positives and negatives of purging. It makes me want to be more thoughtful when I purge.
I was about to get rid of some Stuart Weitzman black patent booties but as I look around, I've seen black patent coming back up for this fall/winter. I think I'll hold onto them for a while longer.
As for regrets, I got rid of a tunic sweater in the perfect shade of light gold that looked great with my hair/complexion. It's one of those colors that is really hard to find. It was about 10 years old but would be great to have now.