Has anyone ever regretted doing a major closet sweep?

I just did an "out with the old, in the with new year" sweep and my criteria was:
1) I had to love it
2) It had to fit what I see as "my" style (which has developed since YLF this fall)
3) I had worn it at least once this season

My closet is half empty, and I'm a little panicked. BUT, what I have hanging there is great, and I wear it all the time.

In a way, I feel great, but do you think I've gone too far? For example, there are things that I bought last year that cost good money that I am shedding (an Oilily skirt that is mid-calf that is just not me anymore, for example).