I often find myself considering this question. I've got what I consider to be a 'fair amount' of clothes, I do love clothes, but I'm pretty disciplined about jettisoning things that don't really work for me, so there's a good bit of natural churn that goes on.
I actually feel quite stressed when I have too many clothes as I forget what I've got, and I do like to wear all my clothes, and then I'll read about capsule wardrobes and it all sounds very serene and organised, but then I'll think about the implications of that and I'd find it very limiting. I lull myself to sleep thinking about outfit combinations it's very soothing!
I don't think I ever wear the same outfit more than twice, each individual item yes, but in different ways.
There's no real point to this thread, I'm just interested to hear other people's approach to their wardrobe. I just fancy a bit of wardrobe chat!